You are cordially invited to attend a special meeting of stockholders (the “Special Meeting”) of Duck Creek Technologies, Inc. (“Duck Creek” or the “Company”) to be held on Tuesday, March 28, 2023, at 9:00 a.m., Eastern Time online at https://www.virtualshareholdermeeting.com/DCT2023SM.

At the Special Meeting, you will be asked to consider and vote on a proposal to adopt the Agreement and Plan of Merger, dated as of January 8, 2023 (as it may be amended, supplemented or otherwise modified from time to time, the “Merger Agreement”), by and among Disco Parent, LLC (“Parent”), Disco Merger Sub, Inc., a direct, wholly owned subsidiary of Parent (“Merger Sub”), and Duck Creek. Pursuant to the terms of the Merger Agreement, Merger Sub will merge with and into Duck Creek (the “Merger”), with Duck Creek surviving the Merger and becoming a wholly owned subsidiary of Parent. Parent and Merger Sub are entities that are affiliated with Vista Equity Partners Management, LLC, a leading private equity firm focused on investments in software, data and technology-enabled companies. You will also be asked to consider and vote on a non-binding, advisory proposal to approve compensation that will or may become payable by Duck Creek to its named executive officers in connection with the Merger.

If the Merger contemplated by the Merger Agreement is completed, you will be entitled to receive $19.00 in cash, without interest, for each share of Duck Creek’s common stock, par value $0.01 per share (“Duck Creek Common Stock”) that you own as of immediately prior to the effective time of the Merger unless you have properly exercised your appraisal rights with respect to such shares.

On January 8, 2023, a special committee of Duck Creek’s board of directors (the “Board”), consisting entirely of independent and disinterested directors (the “Special Committee”), reviewed and considered the terms and conditions of the Merger Agreement and the Merger and the other transactions contemplated by the Merger Agreement. After considering various factors, including those described in the accompanying Proxy Statement (the “Proxy Statement”), and after consultation with the Special Committee’s independent legal and financial advisors, the Special Committee unanimously (i) determined that it is in the best interests of the Company and its stockholders, and declared it advisable, to enter into the Merger Agreement providing for the Merger in accordance with the DGCL, (ii) approved and adopted the Merger Agreement and (iii) resolved to recommend that the Board approve and adopt the Merger Agreement. On January 8, 2023, Duck Creek’s Board, after considering various factors, including the unanimous recommendation of the Special Committee and the other factors described in the Proxy Statement, and after consultation with Duck Creek’s independent legal and financial advisors, (i) determined that it is in the best interests of the Company and its stockholders, and declared it advisable, to enter into the Merger Agreement and consummate the Merger and the other transactions contemplated by the Merger Agreement, (ii) declared it advisable and approved and adopted the Merger Agreement, approved the execution and delivery of the Merger Agreement by the Company, the performance by the Company of its covenants and other obligations thereunder, and the consummation of the Merger and the other transactions contemplated by the Merger Agreement upon the terms and conditions set forth therein and (iii) resolved to recommend that the stockholders of Duck Creek vote in favor of the adoption of the Merger Agreement and the approval of the Merger and the other transactions contemplated by the Merger Agreement.

The Board recommends that you vote (i) “FOR” the proposal to adopt the Merger Agreement, thereby approving the Merger, the Merger Agreement and the other transactions contemplated thereby and (ii) “FOR” the proposal to approve, by non-binding, advisory vote, compensation that will or may be payable by Duck Creek to its named executive officers in connection with the Merger.

The enclosed Proxy Statement provides detailed information about the Special Meeting, the Merger Agreement and the Merger. A copy of the Merger Agreement is attached as Annex A to the Proxy Statement. The Proxy Statement also describes the actions and determinations of each of the Special Committee and the Board in connection with its evaluation of the Merger Agreement and the Merger. You are encouraged to read the Proxy Statement and its annexes, including the Merger Agreement, carefully and in their entirety. You may also obtain more information about Duck Creek from documents we file with the United States Securities and Exchange Commission (the “SEC”) from time to time.

We appreciate you taking the time to vote promptly and encourage you to do so electronically. After reading the Proxy Statement, please vote at your earliest convenience by voting over the Internet using the Internet address on the proxy card or by voting by telephone using the toll-free number on the proxy card. If you do not have access to a touch-tone phone or the Internet, you may alternatively vote by signing, dating and returning the enclosed proxy card in the enclosed postage-paid envelope. Only your last-dated proxy will be counted, and any proxy may be revoked at any time prior to its exercise at the Special Meeting.

If your shares of Duck Creek Common Stock are registered directly in your name, you are considered the stockholder of record with respect to those shares. If your shares are held in a stock brokerage account or by a bank or other nominee, then the broker, bank, trust or other nominee is considered to be the stockholder of record with respect to those shares. However, you are still considered to be the beneficial owner of those shares, and your shares are said to be held in “street name.” Street name holders generally cannot submit a proxy or vote their shares directly and must instead instruct the broker, bank, trust or other nominee how to vote their shares using the methods described above. Because the proposals are “non-routine matters,” your broker, bank, trust or other nominee does not have discretionary authority to vote your shares on the proposals. If your shares of Duck Creek Common Stock are held in street name, your broker, bank, trust or other nominee has enclosed a voting instruction form with the Proxy Statement. If you hold your shares in street name and give voting instructions to your broker, bank, trust or other nominee with respect to one of the proposals, but give no instruction as to the other proposal, then those shares will be deemed present at the Special Meeting for purposes of establishing a quorum at the Special Meeting, will be voted as instructed with respect to the proposal as to which instructions were given, and will not be voted with respect to any other proposal. We encourage you to authorize your broker, bank, trust or other nominee to vote your shares “FOR” both of the proposals by following the instructions provided on the enclosed voting instruction form to provide your instructions over the Internet, by telephone or by signing, dating and returning the voting instruction form in the postage-paid envelope provided. We encourage you to vote electronically.

Your vote is very important, regardless of the number of shares that you own. We cannot consummate the Merger unless the proposal to adopt the Merger Agreement is approved by the affirmative vote of a majority of the outstanding shares of Duck Creek Common Stock entitled to vote thereon, provided a quorum is present. In addition, the Merger Agreement makes the approval by the stockholders of Duck Creek (“Company stockholders”) of the proposal to adopt the Merger Agreement a condition to the parties’ obligations to consummate the Merger. The failure of any stockholder of record to grant a proxy electronically over the Internet or by telephone, to submit a signed proxy card, or to vote by virtual ballot at the Special Meeting will have the same effect as a vote “AGAINST” the proposal to adopt the Merger Agreement, will not have any effect on the proposal to approve compensation that will or may become payable by Duck Creek to its named executive officers in connection with the Merger and will cause such stockholder’s shares to not be counted for purposes of determining whether a quorum is present for the transaction of business at the Special Meeting. Abstentions will be counted as votes “AGAINST” the proposal to adopt the Merger Agreement and the proposal to approve compensation that will or may become payable by Duck Creek to its named executive officers in connection with the Merger. Because both proposals presented to stockholders will be considered non-discretionary, we do not anticipate any broker non-votes at the Special Meeting. Broker non-votes will not be considered present for the purposes of establishing a quorum and will not count as votes cast at the Special Meeting, and otherwise will have no effect on a particular proposal.

The Special Meeting will be held virtually and you will be able to attend the meeting and vote via the Internet at https://www.virtualshareholdermeeting.com/DCT2023SM by using the 16-digit control number included in your proxy materials. You will not be able to attend the Special Meeting in person.

If you have any questions about the Proxy Statement, the Special Meeting, the Merger Agreement or the Merger or need assistance with voting procedures, please contact Innisfree M&A Incorporated, our proxy solicitor, by calling (877) 717-3923 (TOLL-FREE from the U.S. and Canada) or +1 (412) 232-3651 (from other locations).

On behalf of the Board, I thank you for your support and appreciate your consideration of these matters.

Neither the SEC nor any state securities regulatory agency has approved or disapproved of the transactions described in this document, including the Merger, or determined if the information contained in this document is accurate or adequate. Any representation to the contrary is a criminal offense.

The Proxy Statement is dated February 28, 2023 and, together with the enclosed form of proxy card, is first being mailed to Company stockholders on or about February 28, 2023.

You are cordially invited to attend a special meeting of stockholders (the “Special Meeting”) of Duck Creek Technologies, Inc. (“Duck Creek” or the “Company”) to be held on Tuesday, March 28, 2023, at 9:00 a.m., Eastern Time online at https://www.virtualshareholdermeeting.com/DCT2023SM.

The Special Meeting will be held for the following purposes:

The affirmative vote of a majority of the outstanding shares of Duck Creek’s common stock, par value $0.01 per share (“Duck Creek Common Stock”) entitled to vote thereon is required to adopt the Merger Agreement. The affirmative vote of the holders of a majority of the total number of votes of Duck Creek Common Stock present at the Special Meeting, or represented by proxy and entitled to vote thereon at the Special Meeting, provided a quorum is present, is required to approve, by means of a non-binding, advisory vote, the proposal to approve compensation that will or may become payable by Duck Creek to its named executive officers in connection with the Merger. The failure of any stockholder of record to grant a proxy electronically over the Internet or by telephone, submit a signed proxy card, or to vote by virtual ballot at the Special Meeting will have the same effect as a vote “AGAINST” the proposal to adopt the Merger Agreement, will not have any effect on the proposal to approve compensation that will or may become payable by Duck Creek to its named executive officers in connection with the Merger and will cause such stockholder’s shares to not be counted for purposes of determining whether a quorum is present for the transaction at business at the Special Meeting. Abstentions will be counted as votes “AGAINST” the proposal to adopt the Merger Agreement and the proposal to approve compensation that will or may become payable by Duck Creek to its named executive officers in connection with the Merger. Because both proposals presented to Company stockholders will be considered non-discretionary, we do not anticipate any broker non-votes at the Special Meeting. Broker non-votes will not be considered present for the purposes of establishing a quorum and will not count as votes cast at the Special Meeting, and otherwise will have no effect on a particular proposal.

Only Company stockholders of record as of the close of business on February 9, 2023 are entitled to notice of the Special Meeting and to vote at the Special Meeting or at any adjournment or postponement thereof. A list of stockholders entitled to vote at the Special Meeting will be available in our principal executive offices located at 22 Boston Wharf Road, Floor 10, Boston, MA 02210, during regular business hours for a period of no less than ten (10) days before the Special Meeting and at the place of the Special Meeting during such meeting. Stockholders may also access the list during the Special Meeting, by using the virtual meeting website link set forth above.

Company stockholders and beneficial owners who do not vote in favor of the proposal to adopt the Merger Agreement will have the right to seek appraisal of the fair value of their shares of Duck Creek Common Stock if they deliver a written demand for appraisal to the Company before the vote is taken on the proposal to adopt the Merger Agreement and otherwise comply with, and do not validly withdraw their demands or otherwise lose their appraisal rights under, the applicable provisions of Delaware law, which are summarized in the Proxy Statement accompanying this notice in the section entitled “Appraisal Rights” beginning on page 106 of the

Proxy Statement. A copy of Section 262 of the General Corporation Law of the State of Delaware, which details the applicable Delaware appraisal statute, may be accessed without subscription or cost at the following publicly available website: https://delcode.delaware.gov/title8/c001/sc09/index.html#262.

Duck Creek’s board of directors (the “Board”) recommends that you vote “FOR” the adoption of the Merger Agreement and “FOR” the non-binding, advisory proposal regarding compensation that will or may become payable by Duck Creek to its named executive officers in connection with the Merger. In considering the recommendation of the Board, Company stockholders should be aware that the Company’s executive officers and members of the Board may have agreements and arrangements in place that provide them with interests in the Merger that may be different from, or in addition to, those of Duck Creek. See the section entitled “The Merger—Interests of the Directors and Executive Officers of Duck Creek in the Merger” beginning on page 72 of the Proxy Statement.

Our Notice of Special Meeting and Proxy Statement are available at www.proxyvote.com.

Your vote is extremely important. Whether or not you plan to virtually attend the Special Meeting and regardless of the number of shares you own, we urge you to vote promptly “FOR” both of the proposals.

If you have any questions about submitting your proxy card or otherwise require assistance, please contact:

The following questions and answers are intended to address some commonly asked questions regarding the Merger, the Merger Agreement and the Special Meeting. These questions and answers may not address all questions that may be important to you as a Company stockholder. You are encouraged to read carefully the more detailed information contained elsewhere in this Proxy Statement, the annexes to this Proxy Statement and the documents we refer to in this Proxy Statement. You may obtain the information incorporated by reference in this Proxy Statement without charge by following the instructions in the section entitled “Where You Can Find More Information” beginning on page 112 of this Proxy Statement.

This Proxy Statement, and the documents to which Duck Creek refers you in this Proxy Statement, as well as information included in oral statements or other written statements made or to be made by Duck Creek or on Duck Creek’s behalf, contain “forward-looking statements” within the meaning of the federal securities laws, including but not limited to, those statements related to the Merger, including financial estimates and statements as to the expected timing, completion and effects of the Merger. You can identify forward-looking statements because they contain words such as “expect,” “believe,” “target,” “project,” “goals,” “estimate,” “potential,” “predict,” “may,” “will,” “might,” “could,” “forecast,” “outlook” and variations of these terms or the negative of these terms and similar expressions. Forward-looking statements, including statements regarding the Merger, are based on the Company’s current expectations and assumptions. Because forward-looking statements relate to the future, they are subject to inherent uncertainties, risks and changes in circumstances that may differ materially from those contemplated by the forward-looking statements, which are neither statements of historical fact nor guarantees or assurances of future performance.

Important factors, risks and uncertainties that could cause actual results to differ materially from such plans, estimates or expectations include but are not limited to: (i) the completion of the Merger on the anticipated terms and timing, including obtaining required stockholder and regulatory approvals, and the satisfaction of other conditions to the completion of the Merger; (ii) potential litigation relating to the Merger that could be instituted against the Company or its directors, managers or officers, including the effects of any outcomes related thereto; (iii) the risk that disruptions from the Merger (including the ability of certain customers to terminate or amend contracts upon a change of control) will harm the Company’s business, including current plans and operations, including during the pendency of the Merger; (iv) the ability of the Company to retain and hire key personnel; (v) potential adverse reactions or changes to business relationships resulting from the announcement or completion of the Merger; (vi) legislative, regulatory and economic developments; (vii) potential business uncertainty, including changes to existing business relationships, during the pendency of the Merger that could affect the Company’s financial performance; (viii) certain restrictions during the pendency of the Merger that may impact the Company’s ability to pursue certain business opportunities or strategic transactions; (ix) unpredictability and severity of catastrophic events, including but not limited to, acts of terrorism, outbreaks of war or hostilities or the COVID-19 pandemic, as well as management’s response to any of the aforementioned factors; (x) the possibility that the Merger may be more expensive to complete than anticipated, including as a result of unexpected factors or events; (xi) the occurrence of any event, change or other circumstance that could give rise to the termination of the Merger, including in circumstances requiring the Company to pay a termination fee; (xii) those risks and uncertainties set forth under the headings “Special Note Regarding Forward-Looking Statements” and “Risk Factors” in the Company’s most recent Annual Report on Form 10-K, as such risk factors may be amended, supplemented or superseded from time to time by other reports filed by the Company with the SEC from time to time, which are available via the SEC’s website at www.sec.gov; and (xiii) the risks described in the Proxy Statement.

There can be no assurance that the Merger will be completed, or if it is completed, that it will close within the anticipated time period. These factors should not be construed as exhaustive and should be read in conjunction with the other forward-looking statements. The forward-looking statements relate only to events as of the date on which the statements are made. The Company does not undertake any obligation to publicly update or review any forward-looking statement except as required by law, whether as a result of new information, future developments or otherwise. If one or more of these or other risks or uncertainties materialize, or if our underlying assumptions prove to be incorrect, our actual results may vary materially from what we may have expressed or implied by these forward-looking statements.

We caution that you should not place undue reliance on any of our forward-looking statements. You should specifically consider the factors identified in this communication that could cause actual results to differ. Furthermore, new risks and uncertainties arise from time to time, and it is impossible for us to predict those events or how they may affect the Company.

This Proxy Statement is being furnished to Company stockholders as a part of the solicitation of proxies by the Board for use at the Special Meeting to be held on Tuesday, March 28, 2023, at 9:00 a.m., Eastern Time or at any adjournment or postponement thereof. Duck Creek will hold the Special Meeting in a virtual format only at https://www.virtualshareholdermeeting.com/DCT2023SM.

At the Special Meeting, Company stockholders will be asked to consider and vote on proposals to:

Only Company stockholders of record as of the close of business on February 9, 2023 are entitled to notice of the Special Meeting and to vote at the Special Meeting or at any adjournment or postponement thereof. A list of stockholders entitled to vote at the Special Meeting will be available for inspection in Duck Creek’s headquarters located at 22 Boston Wharf Road, Floor 10, Boston, MA 02210, during regular business hours for a period of at least ten (10) days before the Special Meeting and at the location of the Special Meeting during the Special Meeting. To access the list during the Special Meeting, please use the virtual meeting website link set forth above.

The inspector of elections appointed for the Special Meeting will tabulate votes cast by proxy or by ballot at the Special Meeting. The inspector of elections will also determine whether a quorum is present. The presence of a majority of the outstanding shares of Duck Creek Common Stock entitled to vote at the Special Meeting constitutes a quorum. Shares that abstain from voting on any proposal will be treated as shares that are present and entitled to vote at the Special Meeting for purposes of determining whether a quorum is present.

With respect to shares held in street name, your broker, bank, trust or other nominee generally has the discretionary authority to vote uninstructed shares on “routine” matters, but cannot vote such uninstructed shares on “non-routine” matters. Because the Special Meeting Proposals presented to Company stockholders are considered non-discretionary, there will not be any broker non-votes at the Special Meeting. Broker non-votes will not be considered present for the purposes of establishing a quorum and will not count as votes cast at the Special Meeting, and otherwise will have no effect on a particular proposal.

The affirmative vote of a majority of the outstanding shares of Duck Creek Common Stock, including unvested Company RSAs, entitled to vote thereon is required to adopt the Merger Agreement. The affirmative vote of the holders of a majority of the total number of votes of Duck Creek Common Stock, including unvested Company RSAs, present at the Special Meeting, or represented by proxy and entitled to vote thereon, at the Special Meeting, provided a quorum is present, is required to approve, by means of a non-binding, advisory vote, the proposal to approve compensation that will or may become payable by Duck Creek to its named executive officers in connection with the Merger. This means that the proposal to adopt the Merger Agreement, and the transaction contemplated thereby, including the Merger, will be approved if the number of shares voted “FOR” such proposal is greater than fifty percent (50%) of the total number of outstanding shares of Duck Creek Common Stock entitled to vote at the Special Meeting. Abstentions will have the same effect as votes “AGAINST” the proposal to adopt the Merger Agreement and the transactions contemplated by the Merger Agreement, including the Merger and the proposal to approve compensation that will or may become payable by Duck Creek to its named executive officers in connection with the Merger. Because both proposals presented to Company stockholders will be considered non-discretionary, we do not anticipate any broker non-votes at the Special Meeting. Broker non-votes will not be considered present for the purposes of establishing a quorum and will not count as votes cast at the Special Meeting, and otherwise will have no effect on a particular proposal. However, if you hold your shares in street name and give voting instructions to your

broker, bank, trust or other nominee with respect to one of the proposals, but give no instruction as to the other proposal, then those shares will be deemed present at the Special Meeting for purposes of establishing a quorum at the Special Meeting, will be voted as instructed with respect to the proposal as to which instructions were given, and will not be voted with respect to any other proposal.

As of February 9, 2023, the Record Date, Duck Creek’s directors and executive officers beneficially owned, and were entitled to vote, in the aggregate, 3,733,584 shares of Duck Creek Common Stock, consisting of 2,098,465 shares of unrestricted Duck Creek Common Stock and 1,635,119 unvested Company RSAs, representing approximately 2.7% of the outstanding shares of Duck Creek Common Stock. We expect that Duck Creek’s directors and executive officers will beneficially own and be entitled to vote a similar figure at the close of business on the date of the Special Meeting. The directors and executive officers have informed Duck Creek that they currently intend to vote all of their shares of Duck Creek Common Stock and “FOR” the adoption of the Merger Agreement, and “FOR” the non-binding, advisory proposal regarding compensation that will or may become payable by Duck Creek to its named executive officers in connection with the Merger.

If your shares are registered in your name with Duck Creek’s transfer agent, American Stock Transfer & Trust Company, LLC, you may cause your shares to be voted by submitting electronically over the Internet or by phone a proxy authorizing the voting of your shares by following the instructions on your proxy card. You must have the enclosed proxy card available, and follow the instructions on the proxy card, in order to submit a proxy electronically over the Internet or by telephone. We encourage all stockholders to vote electronically. Alternatively, if you do not have access to a touch-tone phone or the Internet, you may sign, date and return the enclosed proxy card in the postage-paid envelope provided. Based on your proxy cards or Internet and telephone proxies, the proxy holders will vote your shares according to your directions.

If you plan to attend and desire to vote at the Special Meeting in a virtual format, you will be provided with a virtual ballot at the Special Meeting. Please note that if your shares of Duck Creek Common Stock are held of record by a broker, bank, trust or other nominee, and you decide to attend and vote at the Special Meeting in a virtual format, your vote by virtual ballot at the Special Meeting will not be effective unless you present a legal proxy, issued in your name from your broker, bank, trust or other nominee. Even if you plan to attend the Special Meeting, we encourage you to submit your proxy to vote your shares in advance of the Special Meeting.

Voting instructions are included on your enclosed proxy card. All shares represented by properly executed proxies received in time for the Special Meeting will be voted at the Special Meeting in accordance with the instructions of the Company stockholders. Properly executed proxies that do not contain voting instructions will be voted “FOR” adoption of the Merger Agreement and “FOR” the proposal to approve, by non-binding, advisory vote, compensation that will or may become payable by Duck Creek to its named executive officers in connection with the Merger. No proxy that is specifically marked against adoption of the Merger Agreement will be voted in favor of the proposed compensation arrangements for Duck Creek’s named executive officers in connection with the Merger, unless it is specifically marked “FOR” the approval of such proposal.

If your shares of Duck Creek Common Stock are held in street name and you do not instruct your broker, bank, trust or other nominee how to vote your shares, then, because both of the Special Meeting Proposals are “non-routine matters,” your broker, bank, trust or other nominee would not have discretionary authority to vote your shares on the Special Meeting Proposals. If your shares of Duck Creek Common Stock are held in street name, your broker, bank, trust or other nominee has enclosed a voting instruction form with this Proxy Statement. We encourage you to authorize your broker, bank, trust or other nominee to vote your shares “FOR” both of the Special Meeting Proposals by following the instructions provided on the voting instruction form. If you do not vote via the Internet or telephone through your broker, bank, trust or other nominee or do not return your bank’s, broker’s or other nominee’s voting form, or do not attend the Special Meeting and vote with a proxy from your broker, bank, trust or other nominee, it will be counted as a vote “AGAINST” the proposal to adopt the Merger Agreement and will not have any effect on the proposal to approve, by non-binding, advisory vote, compensation that will or may become payable by Duck Creek to its named executive officers in connection with the Merger. If you hold your shares in street name and give voting instructions to your broker, bank, trust or other nominee with respect to one of the proposals, but give no instruction as to the other proposal,

then those shares will be deemed present at the Special Meeting for purposes of establishing a quorum at the Special Meeting, will be voted as instructed with respect to the proposal as to which instructions were given, and will not be voted with respect to any other proposal.

You may change or revoke your previously submitted proxy at any time before the Special Meeting or, if you attend the Special Meeting in a virtual format, by voting by virtual ballot at the Special Meeting. If you hold your shares as a record holder, you may change or revoke your proxy in any one of the following ways:

Please note that to be effective, your new proxy card, Internet or telephonic voting instructions or written notice of revocation must be received by Duck Creek’s Secretary prior to the Special Meeting.

If your shares are held in street name by a broker, bank, trust or other nominee, you may change your voting instructions by following the instructions of your broker, bank, trust or other nominee. You may also vote at the Special Meeting by ballot if you register in advance to attend the Special Meeting following the procedures described below and if you provide a valid legal proxy from your broker, bank, trust or other nominee.

Any adjournment, recess or postponement of the Special Meeting for the purpose of soliciting additional proxies will allow Company stockholders who have already sent in their proxies to revoke them at any time prior to their use at the Special Meeting which was adjourned, recessed or postponed.

If a quorum is not present or if there are not sufficient votes for the approval of the proposal to adopt the Merger Agreement, Duck Creek expects that the Special Meeting will be adjourned by the chairman of the Special Meeting pursuant to Duck Creek’s bylaws to solicit additional proxies in accordance with the Merger Agreement. At any subsequent reconvening of the Special Meeting, all proxies will be voted in the same manner as the manner in which such proxies would have been voted at the original convening of the Special Meeting, except for any proxies that have been validly revoked or withdrawn prior to the subsequent meeting.

If the Special Meeting is adjourned, we are not required to give notice of the time and place of the adjourned meeting if announced at the Special Meeting at which the adjournment is taken, unless the adjournment is for more than thirty (30) days or the Board fixes a new record date for the Special Meeting. At any adjourned meeting, any business may be transacted which might have been transacted at the original Special Meeting.

If Duck Creek experiences technical difficulties during the Special Meeting (e.g., a temporary or prolonged power outage), it will determine whether the Special Meeting can be promptly reconvened (if the technical difficulty is temporary) or whether the Special Meeting will need to be reconvened on a later day (if the technical difficulty is more prolonged). In any such situation, Duck Creek will promptly notify stockholders of the decision via the virtual meeting website.

Technical support will be ready to assist you with any individual technical difficulties you may have accessing the virtual meeting website. Contact information for technical support will appear on the virtual meeting login page prior to the start of the Special Meeting.

All votes will be tabulated by the inspector of elections appointed for the Special Meeting. The inspector of elections will separately tabulate affirmative and negative votes and abstentions.

The cost of this proxy solicitation will be borne by Duck Creek. Our directors, officers and employees may solicit proxies in person, by mail, telephone, facsimile and email, or by other electronic means. We will pay these directors, officers and employees no additional compensation for these services. We will reimburse banks, brokers and other nominees for their reasonable, out-of-pocket expenses incurred in forwarding this Proxy Statement and related materials to, and obtaining instructions relating to such materials from, beneficial owners of Duck Creek Common Stock.

Duck Creek has retained Innisfree as its proxy solicitor. Innisfree will solicit proxies in person, by mail, telephone, facsimile and email, or by other electronic means. Under our agreement with Innisfree, unless otherwise agreed by the parties, Innisfree will receive an estimated fee not to exceed $45,000 plus reimbursement of its reasonable, out-of-pocket expenses for its services and plus fees for calls (if any) to Company stockholders. In addition, Innisfree and certain related persons will be indemnified against certain liabilities arising out of or in connection with the engagement.

Assuming timely satisfaction of necessary closing conditions, including, among other things, the Requisite Stockholder Approval and receipt of required regulatory approvals, we currently anticipate that the Merger will be consummated in the first half of 2023.

Stockholders may log into the Special Meeting using the 16-digit control number on their proxy cards. Once admitted to the Special Meeting, stockholders may vote their shares and view a list of stockholders by following the instructions available on the meeting website.

The virtual meeting site is supported on Internet browsers and devices (e.g., desktops, laptops, tablets and smart phones) running the most updated version of applicable software and plugins. Each participant should ensure strong WiFi or other Internet connection, allow plenty of time to log in and ensure that he or she can hear streaming audio prior to the start of the Special Meeting.

To vote during the Special Meeting, you must do so by logging into https://www.virtualshareholdermeeting.com/DCT2023SM using the 16-digit control number included in your proxy materials. After accessing the Special Meeting as described above, stockholders of record may vote by clicking on the Stockholder Ballot link on the Special Meeting site, completing the electronic ballot, and clicking ‘Submit’ to have it sent directly to the inspector of elections before the polls are closed at the Special Meeting.

Stockholders of record are reminded that they can vote their shares prior to the Special Meeting over the Internet using the website indicated on the proxy card, by telephone using the toll-free number on the proxy card or by signing, dating and returning the proxy card in the postage-paid envelope previously provided. We encourage shareholders to vote electronically. If you have submitted your vote by proxy in advance of the Special Meeting, you do not need to vote by ballot, unless you wish to change your vote.

A beneficial owner who holds shares through a broker, bank, trust or other nominee and intends to vote at the Special Meeting must present a legal proxy, issued in its name from its broker, bank, trust or other nominee, in order for its vote to be effective. This legal proxy must be saved as a PDF or image file format and attached with its electronic ballot, using the ‘Choose File’ button on the ballot, during the Special Meeting.

After accessing the Special Meeting as described above, beneficial owners may vote by clicking on the Stockholder Ballot link on the Special Meeting site, completing the electronic ballot, attaching their legal proxy

using the ‘Choose File’ button on the ballot, and clicking ‘Submit’ to have it sent directly to the inspector of election before the polls are closed at the Special Meeting. The voting instruction form received by stockholders in connection with the Special Meeting is not a legal proxy.

Beneficial owners are reminded that they can instruct their brokers, banks or other nominees to vote their shares prior to the Special Meeting by following the directions on the voting instruction form to provide their instructions over the Internet, by telephone or by signing, dating and returning the voting instruction form in the postage-paid envelope previously provided. We encourage shareholders to submit their instructions to their brokers, banks or other nominees electronically. If you have submitted your instructions to your bank, broker, bank, trust or other nominee in advance of the Special Meeting, you do not need to vote by ballot, unless you wish to change your vote. Please note that if you request a legal proxy from your bank, broker, bank, trust or other nominee, it will automatically revoke any instructions you may have previously given to that bank, broker, bank, trust or other nominee.

If you need assistance in completing your proxy card or have questions regarding the Special Meeting, please contact Innisfree, our proxy solicitor, by calling (877) 717-3923 (TOLL-FREE from the U.S. and Canada) or +1 (412) 232-3651 (from other locations). Brokers, banks and other nominees may call collect at (212) 750-5833.

The discussion of the Merger in this section and elsewhere in this Proxy Statement is qualified in its entirety by reference to the complete text of the Merger Agreement, a copy of which is attached as Annex A to this Proxy Statement and is incorporated into this Proxy Statement by reference. This summary does not purport to be complete and may not contain all of the information about the Merger that is important to you. You are encouraged to read the Merger Agreement carefully and in its entirety as it is the legal document that governs the Merger.

Additional information about Duck Creek may be found elsewhere in this Proxy Statement and in Duck Creek’s other public filings. See the section entitled “Where You Can Find More Information” beginning on page 112 of this Proxy Statement.

Duck Creek is the leading cloud-based SaaS provider of core systems for the global property and casualty (P&C) and general insurance industry. Core systems comprise the end-to-end back-office infrastructure of insurance companies and include underwriting, rating and policy management; billing and payments; distribution management; claims management; reinsurance management; and data insights. Insurance companies choose Duck Creek’s solutions for its flexibility and seamless cloud-based deployment or on-premises deployment, based on a respective insurance company’s technology strategy.

Duck Creek Common Stock is currently listed on the Nasdaq under the symbol “DCT.”

Parent was formed on January 6, 2023, solely for the purpose of engaging in the transactions contemplated by the Merger Agreement, including the Merger and the related financing transactions. Parent has not engaged in any business activities other than in connection with the transactions contemplated by the Merger Agreement and arranging of the equity financing in connection with the merger.

Merger Sub is a direct, wholly owned subsidiary of Parent and was formed on January 6, 2023, solely for the purpose of engaging in the transactions contemplated by the Merger Agreement, including the Merger, and has not engaged in any business activities other than in connection with the transactions contemplated by the Merger Agreement.

Parent and Merger Sub are each affiliated with Vista Fund VIII, and Vista Fund VIII is affiliated with Vista. Vista is a leading private equity firm focused on investments in software, data and technology-enabled companies.

In connection with the transactions contemplated by the Merger Agreement, Vista Fund VIII has provided Parent with an equity commitment of up to approximately $2.65 billion, which will be available, together with cash on hand at Duck Creek as of the Closing, to fund the aggregate merger consideration and to pay the fees, expenses and other amounts required to be paid in connection with the Closing by Duck Creek, Parent and Merger Sub. For more information, please see the section entitled “The Merger—Financing of the Merger” beginning on page 76 of this Proxy Statement.

The Merger Agreement provides that, upon the terms and subject to the conditions of the Merger Agreement, and in accordance with the DGCL, at the Effective Time, Merger Sub will be merged with and into Duck Creek, whereupon the separate corporate existence of Merger Sub will thereupon cease, and Duck Creek will continue as the Surviving Corporation. As a result of the Merger, the Surviving Corporation will become a wholly owned subsidiary of Parent and Duck Creek Common Stock will no longer be publicly traded. In addition, Duck Creek Common Stock will be delisted from Nasdaq and deregistered under the Exchange Act, in each case, in accordance with applicable laws, rules and regulations, and Duck Creek will no longer file periodic reports with the SEC on account of Duck Creek Common Stock. If the Merger is consummated, you will not own any shares of capital stock of the Surviving

Corporation. The Effective Time will occur upon the filing of a certificate of merger with, and the acceptance for record of such filing by, the Secretary of State of the State of Delaware (or at such later time as Duck Creek and the Buyer Parties may agree and specify in the certificate of merger).

If the Merger Agreement is not adopted by the Company stockholders, or if the Merger is not consummated for any other reason:

Upon the consummation of the Merger, each share of Duck Creek Common Stock outstanding as of immediately prior to the Effective Time (other than the Owned Company Shares or the Dissenting Company Shares, as applicable) will be cancelled and extinguished and automatically converted into the right to receive the Per Share Price. Each Owned Company Share will be cancelled and extinguished without any conversion thereof or consideration paid therefor.

Company RSAs. At the Effective Time, each Company RSA, whether vested or unvested, that is outstanding as of immediately prior to the Effective Time will be fully vested, cancelled and automatically converted into the right to receive an amount in cash equal to (A) the number of shares of Duck Creek Common Stock subject to such Company RSA, multiplied by (B) $19.00. Notwithstanding the foregoing, the cash amount relating to each Company RSA granted after January 8, 2023 will not be fully vested and will instead remain subject to the same terms and conditions and be paid out on the same vesting schedule as applied to such Company RSA prior to the Effective Time, subject to the holder’s continued employment or service through the applicable vesting date.

Company RSUs. At the Effective Time, each Company RSU, whether vested or unvested, that is outstanding as of immediately prior to the Effective Time will be fully vested, cancelled and automatically converted into the right to receive an amount in cash equal to (A) the number of shares of Duck Creek Common Stock subject to such Company

RSU, multiplied by (B) $19.00. Notwithstanding the foregoing, the cash amount relating to each Company RSU that was granted after January 8, 2023 will not be fully vested and will instead remain subject to the same terms and conditions and be paid out on the same vesting schedule as applied to such Company RSU prior to the Effective Time, subject to the holder’s continued employment or service through the applicable vesting date.

Company Phantom Stock Awards. At the Effective Time, each Company Phantom Stock Award, whether vested or unvested, that is outstanding as of immediately prior to the Effective Time will be fully vested, cancelled and automatically converted into the right to receive an amount in cash equal to (A) the number of shares of Duck Creek Common Stock measured by reference to such Company Phantom Stock Award, multiplied by (B) $19.00.

Company Options and Company SARs. At the Effective Time, each Company Option and Company SAR will be cancelled immediately upon the Effective Time without payment or consideration.

The Board and the Company’s senior management periodically review the Company’s long-term strategic plan with the goal of maximizing stockholder value. As part of these ongoing evaluations, the Board and the Company’s senior management have, from time to time, considered various strategic alternatives, including the continued execution of the Company’s strategy as a stand-alone public company or the possible sale of the Company to, or combination of the Company with, a third party.

On August 2, 2022, Mr. Wright, Chairman of the Board and a partner at Apax Partners, LLP (collectively, with its affiliates, “Apax”), met for dinner with a representative of a private equity firm (“PE Firm A”), at which they discussed the Company generally. No terms of a potential transaction were discussed.

Following an introduction by Mr. Wright, Mr. Jackowski, the Chief Executive Officer of the Company, and representatives of another private equity firm (“PE Firm B”) met on August 15, 2022, via videoconference, and discussed the insurance software industry generally, and recent developments in the industry. No terms of a potential transaction were discussed.

On August 17, 2022, at the request of another private equity firm (“PE Firm C”), Mr. Jackowski and a representative of PE Firm C met via videoconference and discussed the insurance software industry generally, and potential opportunities for PE Firm C and the Company to work together. No terms of a potential transaction were discussed.

On August 19, 2022, representatives of PE Firm A and a portfolio company owned by PE Firm A (“Company A”) had an introductory call with Mr. Wright, during which they discussed, on a high-level and preliminary basis, the potential interest of PE Firm A and Company A in exploring a strategic transaction with the Company. No terms of a potential transaction were discussed.

On August 30, 2022, Mr. Jackowski met with the chief executive officer of Company A via video conference. The meeting consisted of an introduction between Mr. Jackowski and the chief executive officer of Company A and a high-level acknowledgment between them that the two companies could be interested in exploring a potential strategic transaction. No terms of a potential transaction were discussed.

On September 21, 2022, Mr. Jackowski and Mr. Rhodes, the Chief Financial Officer of the Company, met in person with representatives of PE Firm B, and attended a dinner together following their meeting. The discussions at the meeting and at the dinner were introductory in nature. The parties discussed on a high level PE Firm B’s potential interest in exploring a strategic transaction involving the Company. No terms of a potential transaction were discussed.

On September 22, 2022, Mr. Jackowski and Mr. Rhodes met in person with the chief executive officer, chief financial officer and chief products officer of Company A and representatives of PE Firm A. The discussions at the meeting were preliminary in nature. The parties discussed on a high level the possibility of a strategic transaction involving the Company, PE Firm A and Company A. The representatives at the meeting also discussed, at a high level, certain changes the Company could implement in its expenditures, including its investment in new products, if it ceased to be a public company. No terms of a potential transaction were discussed.

As a follow-up to the meeting between Mr. Jackowski and a representative of PE Firm C on August 17, 2022, a representative of PE Firm C called Mr. Jackowski on September 26, 2022 to discuss on a high level

PE Firm C’s potential interest in exploring a strategic transaction involving the Company. On September 27, 2022, Mr. Jackowski and Mr. Rhodes met with representatives of PE Firm C to further discuss their interest in the Company. No terms of a potential transaction were discussed at either of these meetings.

On October 3, 2022, the Board held a meeting with all members of the Board and representatives of Skadden, Arps, Slate, Meagher & Flom LLP (“Skadden”), the Company’s outside legal counsel, in attendance. At the meeting, Mr. Wright updated the Board on the indications of interest that had been received from PE Firm A, PE Firm B and PE Firm C in exploring a potential transaction with the Company. Mr. Jackowski updated the Board on the meetings Mr. Jackowski and Mr. Rhodes held with representatives of PE Firm B on September 21, 2022, with PE Firm A and Company A on September 22, 2022, and with PE Firm C on September 26, 2022 and on September 27, 2022. Mr. Jackowski informed the Board that no non-public information had been shared with such parties and that there had not been any discussion with any party about the Company’s valuation, the price or terms of any potential transaction, or the potential role of the Company’s current management after a potential transaction.

During the meeting, Mr. Wright stated that Apax would be supportive of a potential sale of the Company, if it were on attractive terms. Mr. Nicoll, a member of the Board and a managing director of Accenture plc (“Accenture plc”), stated that Accenture plc would be supportive of exploring potential third-party interest in the Company. The Board determined that it was supportive of conducting further discussions and explorations of third-party interest in the Company. The Board determined to establish an ad hoc transaction committee of the Board (the “Transaction Committee”) to work with management in exploring potential interest in a strategic transaction involving the Company. The Board appointed Mr. Bloom, Mr. Nicoll and Mr. Wright to the Transaction Committee based on their experience with respect to strategic transactions and their availability. The Board did not delegate any decision-making authority to the Transaction Committee. During the meeting, representatives of Skadden reviewed with the Board its fiduciary duties in the event the Board were to pursue a change in control transaction.

During the same meeting, the Board discussed whether to engage a financial advisor to assist Company management and the Board in identifying other parties that might have interest in a strategic transaction involving the Company. The Board considered the Company’s existing investment banking relationships and the qualifications of those investment banks. The Board authorized the Company’s management and the Transaction Committee to contact J.P. Morgan for assistance with the exploratory process for a strategic transaction, based on J.P. Morgan’s qualifications and experience advising, and familiarity with, companies operating in the same industry as the Company.

At this meeting, Company management updated the Board on the status of management’s preparation of a long-range plan for the Company. The Board discussed with management the assumptions to be included in a long-range plan, including with respect to revenue and Adjusted EBITDA growth rates. The Board authorized management to engage an internationally recognized consulting firm with expertise in the Company’s industry to assist Company management in further developing the assumptions which would serve as the basis for the Company’s long-range plan.

Later, on October 3, 2022, at the request of the Board, Mr. Wright contacted representatives of J.P. Morgan to discuss the potential engagement of J.P. Morgan by the Company in connection with the Company’s evaluation of a potential strategic transaction. Mr. Wright informed the J.P. Morgan representatives that the Company had received unsolicited indications of interest from PE Firm A, PE Firm B and, PE Firm C. Mr. Wright requested that J.P. Morgan identify additional strategic parties and financial parties that the Company could consider contacting to solicit indications of interest for a strategic transaction involving the Company.

On October 6, 2022, Mr. Jackowski held a meeting with representatives of Vista, during which they discussed the insurance software industry generally, and potential opportunities for Vista and the Company to work together. No terms of a potential transaction were discussed.

On October 11, 2022, Mr. Wright held a meeting with a representative of another private equity firm (“PE Firm D”) on matters not related to the Company, during which they briefly discussed the Company generally and PE Firm D’s potential interest in exploring a strategic transaction involving the Company. No terms of a potential transaction were discussed.

On October 18, 2022, at the request of Vista, Mr. Jackowski and Mr. Rhodes met with two representatives from Vista. Mr. Jackowski and the Vista representatives met in person, and Mr. Rhodes joined the meeting via videoconference. The parties discussed on a high-level Vista’s interest in exploring a potential strategic transaction involving the Company. No terms of a potential transaction were discussed.

On October 27, 2022, Vista submitted an oral, non-binding, preliminary indication of interest for a strategic transaction involving the Company, with a preliminary offer price of $15.00 per share of Duck Creek Common Stock, in cash.

Between October 3, 2022 and November 30, 2022, J.P. Morgan, together with members of the Transaction Committee and Company management, identified strategic parties and financial parties that the Company could consider contacting to solicit indications of interest for a strategic transaction involving the Company. The Transaction Committee directed J.P. Morgan to contact approximately 17 strategic and financial parties, including Vista, PE Firm A, Company A, PE Firm B, PE Firm C and PE Firm D, to assess (or follow up on, in the case of potential counterparties who had already been in contact with the Company) their interest in exploring a potential strategic transaction involving the Company. During that period, Mr. Jackowski and Mr. Rhodes also met with a number of those potential counterparties to discuss at a high level the Company’s business and, on a preliminary and high-level basis, the party’s interest in a potential transaction involving the Company. In those initial meetings, no non-public information regarding the Company was shared and no terms of any potential transaction were discussed. These initial meetings included a meeting on October 18, 2022 among Mr. Jackowski, Mr. Rhodes and representatives of Vista, and a meeting on November 4, 2022 between Mr. Jackowski and a representative of Vista. In addition, on October 26, 2022, Mr. Jackowski and Mr. Rhodes met with investment professionals from Vista at an investor conference, which was unrelated to any potential transaction, and no potential transaction was discussed.

On November 2, 2022, the chief executive officer of another strategic party (“Company B”), which was among the parties contacted by J.P. Morgan after the Board meeting on October 3, 2022, contacted J.P. Morgan to request a management presentation from the Company and requested that Company B be sent a draft confidentiality agreement. The Company entered into a confidentiality agreement with Company B on November 8, 2022, which included customary standstill provisions (which standstill terminated, in accordance with its terms, upon the Company’s entry into the Merger Agreement).

On November 14, 2022, Mr. Wright met with representatives of PE Firm A to discuss, on a preliminary basis, a potential strategic transaction among the Company, PE Firm A and Company A. Representatives of J.P. Morgan also attended this meeting on behalf of the Company. During the course of the meeting, representatives of PE Firm A presented various preliminary and high-level financial data generated by PE Firm A regarding a potential strategic transaction, including PE Firm A’s suggestion that a combination of the Company with Company A could potentially result in meaningful synergies. PE Firm A’s presentation posited an illustrative offer price of $15.00 per share of Duck Creek Common Stock, in cash. The parties present at the meeting did not discuss PE Firm A’s preliminary views in detail; however, Mr. Wright and the J.P. Morgan representatives informed PE Firm A that although the Board had not previously discussed any potential offer price, it was their expectation that an offer price would need to be significantly higher than $15.00 per share of Duck Creek Common Stock in order for the Board to consider a sale of the Company. The parties present at the meeting discussed at a high level, among other things, that, if the Company and Company A were to combine, they would together be able to make larger investments in product development. No other terms of any potential transaction, business plans or financial or other analyses or proposals were discussed.

On November 16, 2022, Mr. Jackowski and Mr. Rhodes met in person with representatives of PE Firm C. During the meeting, representatives of PE Firm C informed Mr. Jackowski and Mr. Rhodes that PE Firm C was not interested in pursuing a strategic transaction with the Company at this time, but could be interested in providing funding to a potential acquirer of the Company if such an opportunity were to arise in the future.

In the afternoon of November 16, 2022, Mr. Jackowski and Mr. Rhodes met in person with representatives of Company B. At the meeting, Mr. Jackowski and Mr. Rhodes presented an overview of certain publicly available information about the Company and its business, and the parties present at the meeting discussed the insurance software industry generally.

On November 18, 2022, representatives of another private equity firm (“PE Firm E”) met with Mr. Jackowski and Mr. Rhodes to discuss PE Firm E’s preliminary interest in a strategic transaction involving the Company.

On November 21, 2022, Mr. Jackowski, Mr. Rhodes and representatives of J.P. Morgan, and on November 22, 2022, Mr. Rhodes and representatives of J.P. Morgan, held additional financial and technology due diligence sessions with representatives of Company B.

On November 22, 2022, PE Firm A submitted a non-binding, preliminary indication of interest for a strategic transaction involving the Company, with a preliminary indicative offer price range of $16.25-$16.50 per share of Duck Creek Common Stock, in cash. PE Firm A’s indication of interest stated that the transaction, if completed, would be structured as an acquisition of the Company by Company A.

On November 28, 2022, PE Firm D and another private equity firm (“PE Firm F”), which had been contacted as part of J.P. Morgan’s outreach to potential counterparties after the October 3, 2022 meeting of the Board, informed representatives of J.P. Morgan verbally of their preliminary interest in jointly pursuing a strategic transaction with the Company, together with one of their shared portfolio companies, and provided J.P. Morgan with a non-binding, preliminary offer price range of $14.00-$16.00 per share of Duck Creek Common Stock, in cash.

On November 30, 2022, another private equity firm (“PE Firm G”) submitted a non-binding, preliminary indication of interest for a strategic transaction involving the Company, with a preliminary indicative offer price range of $14.00-$16.00 per share of Duck Creek Common Stock, in cash.

On November 30, 2022, PE Firm E informed representatives of J.P. Morgan that PE Firm E intended to submit a non-binding, preliminary indication of interest for a strategic transaction involving the Company, with a preliminary indicative offer price range of $15.00-$18.00 per share of Duck Creek Common Stock, in cash, and that PE Firm E would submit a written letter to the Company with its proposal following the meeting of its internal investment committee to approve the proposal. On December 4, 2022, PE Firm E submitted this proposal in writing.

On November 30, 2022, the Transaction Committee held a meeting with all members of the Transaction Committee and with representatives of J.P. Morgan and Skadden in attendance. At the meeting, J.P. Morgan representatives updated the Transaction Committee on the status of the outreaches to potential counterparties and the non-binding indications of interest that had been received to date. During the meeting, Mr. Wright informed the Transaction Committee that, subject to Apax’s investment committee’s approval, a different Apax fund than the fund owning Duck Creek Common Stock might be interested in investing in the buyer group for a strategic transaction involving the Company if the Board determined to pursue a sale of the Company to PE Firm A and Company A (but would not be interested in investing in a buyer group with any other potential counterparty), which interest was new and therefore had not previously been raised with the Transaction Committee or the Board. Mr. Wright further informed the Transaction Committee that PE Firm A was not yet aware of such Apax fund’s potential interest and that there had not been any discussions between Apax and PE Firm A regarding the potential participation of an Apax fund as an investor in such a transaction. Mr. Wright further informed the other members of the Transaction Committee that Apax’s investment committee was scheduled to discuss the matter on December 5, 2022, and that Mr. Wright would update the full Board on Apax’s decision, so that the Board could, if appropriate, determine to implement any appropriate decision-making procedures (including the potential recusal of Mr. Wright and Mr. Mackenzie, the Apax-nominated directors on the Board, from a strategic alternatives review process). During the meeting, Skadden representatives reviewed with the Transaction Committee the fiduciary duties of directors when considering a change in control transaction, recent trends in regulatory review of mergers and acquisitions, and procedural protections the Board could consider if certain directors had interests in a potential transaction that differed from the interests of the Company’s other stockholders.

On December 1, 2022, the Board held a meeting with all members of the Board, except Mr. Rajasekar, and representatives of J.P. Morgan and Skadden in attendance. During the meeting, J.P. Morgan representatives updated the Board on the status of the outreaches to potential counterparties and the non-binding indications of interest that had been received to date. During the meeting, Skadden representatives also reviewed with the Board the fiduciary duties of directors in considering a change in control transaction, procedural protections the Board could consider in the event that certain directors had an interest in a transaction that differed from the interests of the Company’s other stockholders, and how the Board should evaluate closing uncertainty and regulatory risk in determining the value to Company stockholders of any proposal. During the meeting, the Board instructed Mr. Jackowski to, and to cause management to, refrain from engaging in any discussions with potential counterparties with respect to any post-closing employment or equity participation, none of which had occurred to date. Mr. Wright informed the Board that, subject to Apax’s investment committee’s approval, a

different Apax fund than the fund owning Duck Creek Common Stock may potentially be interested in investing in the buyer group for a strategic transaction involving the Company if the Board determined to pursue a sale to PE Firm A and Company A (but would not be interested in investing in a buyer group with any other potential counterparty), and that Mr. Wright would update the Board following a meeting of Apax’s investment committee on December 5, 2022 to discuss the matter, so that the Board could, if appropriate, determine to implement appropriate decision-making procedures (including the potential recusal of Mr. Wright and Mr. Mackenzie, the Apax-nominated directors on the Board, from a strategic alternatives process).

At this meeting, Mr. Jackowski also updated the Board on the continuing work by Company management to use the draft long-range plan to develop the Stand-Alone Projections (as defined in the section entitled “The Merger—Forecasts” beginning on page 68 of this Proxy Statement). The Board discussed and provided input on the draft Stand-Alone Projections, asked for more detail in various areas and instructed Company management to prepare and circulate a further revised draft of the Stand-Alone Projections incorporating the Board’s input in advance of the next meeting of the Board, scheduled for December 4, 2022.

On December 4, 2022, the Board held a meeting with all members of the Board and representatives of J.P. Morgan and Skadden in attendance. The Board reviewed with Company management the further revised draft of the Stand-Alone Projections, and Mr. Rhodes explained the modifications that had been made in the current draft based on the Board’s questions and comments at its prior meeting. Mr. Jackowski reviewed certain metrics with the Board, including 2022 revenue of the Company, the Company’s estimated 2023 revenue, and how revenue and Adjusted EBITDA in 2022 and estimated revenue and Adjusted EBITDA for 2023 compared with models prepared by the Company in connection with its IPO. The Board requested additional detail and comparisons from Company management to review before approving the draft Stand-Alone Projections. At the meeting, J.P. Morgan representatives reviewed with the Board the status of the outreaches to potential counterparties. Skadden representatives further discussed with the Board certain procedural protections the Board could consider if an Apax fund, with the approval of the Apax investment committee determined it were interested in investing in a buyer group for a strategic transaction.

On December 5, 2022, the Board held a meeting with all members of the Board and representatives of J.P. Morgan and Skadden in attendance. Mr. Wright informed the Board that an Apax fund, with the approval of the Apax investment committee, had determined to evaluate whether such Apax fund would be interested in potentially pursuing an investment in the buyer group for a strategic transaction involving the Company with PE Firm A and Company A, if the Board determined to pursue a sale of the Company to PE Firm A and Company A (but would not be interested in investing in a buyer group with any other potential counterparty). In light of an Apax fund’s interest in evaluating whether to pursue such a transaction, the Board determined to dissolve the Transaction Committee and establish a special committee of the Board (the “Special Committee”) comprised of independent and disinterested directors of the Board. The Board appointed Mr. Bloom, Ms. Dodd and Mr. Nicoll to serve as members of the Special Committee. In selecting Mr. Nicoll to serve on the Special Committee and concluding that he was disinterested and independent, the Board considered Mr. Nicoll’s affiliation with Accenture plc, and the fact that Mr. Nicoll, on behalf of Accenture plc, had indicated during the Board meeting held on October 3, 2022 that Accenture plc was not interested in participating in a potential transaction as a buyer. The Board delegated to the Special Committee the power and authority of the Board, to the fullest extent permitted by law and the Company’s bylaws, to consider, negotiate and evaluate the terms, conditions and advisability of any strategic transaction involving the Company, to oversee negotiations of any strategic transaction, and to reject any strategic transaction. The Board resolutions forming the Special Committee also provided that the Board would not approve any strategic transaction, or recommend that the Company’s stockholders approve any strategic transaction, that was not recommended by the Special Committee. The Board also granted the Special Committee the authority to engage, at the Company’s expense, its own legal, investment banking, accounting and other advisors or consultants to assist the Special Committee as the Special Committee determined appropriate in its sole discretion.

At this meeting, after further review of the information requested by the Board from Company management at its meeting on December 4, 2022 and after further discussion, the Board approved the Stand-Alone Projections.

Mr. Wright and Mr. Mackenzie then left the meeting, and J.P. Morgan representatives presented to the rest of the Board J.P. Morgan’s preliminary financial analyses of the Company, including analyses based on the Stand-Alone Projections. J.P. Morgan representatives also updated the Board on the outreaches to potential counterparties to date, and the indications of interest received to date.

On December 5, 2022 and December 6, 2022, representatives of Apax, including Mr. Wright and Mr. Mackenzie, met with representatives of PE Firm A, who are also members of the board of directors of Company A, to discuss at a preliminary and high level the possibility of a potential equity investment by an Apax fund in Company A in connection with a strategic transaction among PE Firm A, Company A and the Company. The discussions were exploratory in nature, and were part of the Apax fund’s evaluation of whether such Apax fund would be interested in potentially pursuing an investment in a strategic transaction involving the Company with PE Firm A and Company A. Apax representatives later informed the Special Committee of such discussions.

On December 6, 2022, Mr. Rhodes held an introductory call with representatives of another private equity firm (“PE Firm H”), which had been contacted as part of J.P. Morgan’s outreaches to potential counterparties after the October 3, 2022 meeting of the Board, to discuss at a high level the Company’s business and the insurance software industry generally. No non-public information regarding the Company was shared and no terms of any potential transaction were discussed.

The Special Committee considered recommendations for law firms and interviewed law firms seeking to act as independent counsel to the Special Committee. After considering presentations of these law firms to the Special Committee, and the respective qualifications, reputation and experience of these and other law firms, on December 7, 2022, the Special Committee selected Paul, Weiss, Rifkind, Wharton & Garrison LLP (“Paul, Weiss”) to act as its independent legal counsel.

On December 8, 2022, the Special Committee held a meeting with all members of the Special Committee and representatives of Paul, Weiss in attendance, to discuss initial matters to facilitate the Special Committee’s oversight of the process for exploring a potential strategic transaction involving the Company, including the engagement by the Special Committee of an independent financial advisor.

The Special Committee discussed the benefits of engaging J.P. Morgan as the Company’s financial advisor and the need to understand if any of J.P. Morgan’s relationships with the Company, Apax and the other potential counterparties could adversely affect J.P. Morgan’s ability to act as an unconflicted advisor. After this discussion, representatives of J.P. Morgan joined the meeting and updated the Special Committee on the status of the outreaches to potential counterparties and the non-binding indications of interest J.P. Morgan and the Company had received. The Special Committee interviewed the J.P. Morgan representatives about J.P. Morgan’s past engagements with, and the fees J.P. Morgan and its affiliates have earned from, the Company, Apax and certain other potential counterparties to a strategic transaction, the percentage of J.P. Morgan’s revenues derived from work for private equity sponsors, and J.P. Morgan’s perspectives on designing a process that would maximize stockholder value. The J.P. Morgan representatives left the meeting and then provided to the Special Committee, in writing, disclosure of relationships between J.P. Morgan and its affiliates on the one hand, and the Company, Apax and certain other potential counterparties to a strategic transaction, on the other hand, that the J.P. Morgan representatives discussed with the Special Committee during the meeting. After discussion and deliberation, the Special Committee determined that, based on J.P. Morgan’s disclosures, J.P. Morgan’s relationships with potential counterparties, including Apax, should not adversely affect J.P. Morgan’s ability to act as an unconflicted financial advisor for the Company in respect of its evaluation of a potential transaction and that the Special Committee supported J.P. Morgan being engaged as the financial advisor of the Company. The Special Committee also determined that it would engage a second financial advisor who had no prior involvement with the process to date to serve as the independent financial advisor to the Special Committee, and decided to interview two different financial advisors, including Evercore Group L.L.C. (“Evercore”), regarding their qualifications and experience, and relationships with the Company, Apax and the other potential counterparties, for the potential engagement.

On December 8, 2022, representatives of Paul, Weiss contacted legal counsel for Apax to discuss the possibility of a potential equity investment by an Apax fund in Company A in connection with a strategic transaction among PE Firm A, Company A and the Company. Legal counsel for Apax advised Paul, Weiss of the disclosure obligations under Regulation 13D of the Apax fund through which Apax owns Duck Creek Common Stock and informed Paul, Weiss that any such potential equity investment would be undertaken by a new fund as a new investment and that the Apax fund owning Duck Creek Common Stock would intend to sell its shares of Duck Creek Common Stock in a transaction recommended by the Special Committee and approved by the

Board. Representatives of Paul, Weiss and legal counsel for Apax also discussed the applicability of the restrictions on business combinations with interested stockholders under Section 203 of the DGCL (“Section 203”), which could apply to any potential counterparty bidding jointly with an Apax fund, unless the Board granted the counterparty a waiver in advance.

On December 9, 2022 and December 10, 2022, following discussions with Paul, Weiss, the Special Committee provided the other members of the Board (excluding Mr. Wright and Mr. Mackenzie) and certain members of the Company’s management with internal communications guidelines to protect the confidentiality of the Special Committee’s process and ensure that the Special Committee would be able to negotiate with potential counterparties vigorously on an arms’ length basis and effectively execute its mandate. The Special Committee instructed such parties to refrain from discussing the potential strategic transaction or the Special Committee’s process with, and not to provide any information to, any potential counterparty to a transaction involving the Company, including Apax and Apax-nominated directors, without first consulting with the Special Committee.

The Special Committee and representatives of Paul, Weiss met on December 12, 2022 to interview representatives of one potential financial advisor, and on December 13, 2022, to interview representatives of Evercore. In each interview, the Special Committee asked representatives of the financial advisors questions regarding their qualifications and experience in special committee engagements in similar transactions, their past engagements with, and the fees they and their affiliates have earned from, the Company, Apax and the other potential counterparties to a strategic transaction, and their perspectives on designing a process that would maximize stockholder value, and discussed with representatives of the financial advisors their answers. After the conclusion of Evercore’s interview, the Special Committee discussed with Paul, Weiss the qualifications and experience, and relationship disclosure, of each financial advisor.

On December 13, 2022, the Special Committee met again with representatives of Paul, Weiss also in attendance to further discuss the interviews the Special Committee had conducted with representatives of Evercore and representatives of the other potential financial advisor. Following this discussion, the Special Committee determined that it would engage Evercore as its independent financial advisor, based on Evercore’s qualifications and experience advising special committees in circumstances similar to that of the Special Committee, Evercore’s experience advising, and familiarity with, companies in the same industry as the Company and the Special Committee’s determination that Evercore’s relationships with potential counterparties, including Apax, should not adversely affect Evercore’s ability to act as an unconflicted financial advisor for the Special Committee in respect of its evaluation of a potential transaction. The Special Committee directed Paul, Weiss to notify Evercore, J.P. Morgan and the other potential financial advisor the Special Committee had interviewed of the Special Committee’s decision to engage Evercore as the Special Committee’s independent financial advisor.

During its December 13, 2022 meeting, the Special Committee also discussed the importance of confidentiality and deliberate management of information flow to potential counterparties in order to structure a process that would maximize stockholder value. The Special Committee also reviewed with Paul, Weiss the obligations of the Apax fund through which Apax owns Duck Creek Common Stock under Regulation 13D to make public filings disclosing certain changes in its plans or proposals regarding its investment in the Company and the restrictions on business combinations with interested stockholders under Section 203, which could apply to any potential counterparty bidding jointly with Apax, unless the Board granted the counterparty a waiver in advance. The Special Committee considered, among other things, whether to request that Apax cease discussions of a strategic transaction with PE Firm A, Company A and any other potential counterparty until further notice; whether Apax’s ceasing such discussions would be likely to decrease the amount PE Firm A and Company A would be willing to offer in any proposal for a strategic transaction; and whether permitting the discussions to continue would increase the risk of a market leak that could harm the Company’s relations with its customers and employees or decrease competitive dynamics of the process.

Representatives of Apax informed the Special Committee that on December 14, 2022, Apax and Company A entered into a confidentiality agreement with each other, following which, representatives of Apax attended a management presentation about Company A by representatives of Company A. Representatives of Apax informed the Special Committee that only information relating to the business of Company A was presented and discussed at the meeting and that Apax continued to comply with its confidentiality obligations to the Company restricting the disclosure of any confidential information of the Company.

Following Evercore’s selection as the Special Committee’s independent financial advisor on December 13, 2022, and J.P. Morgan’s selection as the Company’s financial advisor on the same day, representatives of Evercore and of J.P. Morgan met from time to time, separately from each other, with members of Company management to review information regarding the Company, including the Stand-Alone Projections. Each financial advisor also continued to work separately to refine its preliminary financial analyses of the Company based on, at the direction of the Board, in the case of J.P. Morgan, and at the direction of the Special Committee, in the case of Evercore, the Stand-Alone Projections.

On December 14, 2022, Paul, Weiss, at the direction of the Special Committee, contacted Apax’s legal counsel to inform them that the Special Committee requested that Apax cease all discussions and communications with PE Firm A and Company A, and any other parties, relating to a strategic transaction involving the Company, until further notice.

On the same day, Mr. Wright received an unsolicited inbound request from another private equity firm (“PE Firm I”) to discuss its potential interest in exploring a strategic transaction involving the Company. Mr. Wright did not respond to PE Firm I’s inbound request and forwarded the request to representatives of Evercore and of J.P. Morgan.

On December 15, 2022, at the direction of the Special Committee, representatives of Evercore and J.P. Morgan discussed with representatives of Apax, and separately, representatives of Paul, Weiss discussed with Apax’s legal counsel, the Special Committee’s request that Apax cease discussions with PE Firm A and Company A. Representatives of Apax informed the Company that later that day, representatives of Apax would inform representatives of PE Firm A and Company A that the Special Committee had requested that Apax, PE Firm A and Company A cease further discussions of a strategic transaction among them involving the Company, and cease further sharing of information by Company A, pending the Special Committee’s consent to further discussions. Each of Apax, PE Firm A and Company A agreed that day to abide by the Special Committee’s request at that time, and PE Firm A and Company A confirmed to the Special Committee that they had not had discussions with Apax about a strategic transaction since December 8, 2022.

On December 15, 2022, Vista submitted a written, non-binding, preliminary indication of interest for a strategic transaction involving the Company, including a preliminary offer price range of $16.00-$18.00 per share of Duck Creek Common Stock, in cash.

Also on December 15, 2022, the Company publicly announced its intention to release its financial results for the fiscal quarter ended November 30, 2022 on January 5, 2023, and to hold an earnings call with analysts on that day.

On December 16, 2022, at the request of the Special Committee, representatives of Evercore provided customary relationship disclosures to the Special Committee, which included disclosure of certain relationships between Evercore and its affiliates, on the one hand, and the Company, Apax, Accenture plc and their respective affiliates and portfolio companies, as applicable, on the other hand.

Also on December 16, 2022, representatives of Apax, Evercore, J.P. Morgan, Paul, Weiss and Apax’s legal counsel had further discussions about Apax’s continued requests to permit an Apax fund to engage in discussions with PE Firm A and Company A and conduct due diligence on Company A to evaluate whether such Apax fund would be interested in potentially pursuing a strategic transaction involving the Company with PE Firm A and Company A.

Later on December 16, 2022, the Special Committee held a meeting with all members of the Special Committee and representatives of each of Evercore, J.P. Morgan and Paul, Weiss in attendance. During the meeting, the Special Committee nominated and elected Mr. Nicoll as the Chair of the Special Committee. The Special Committee discussed with representatives of each of Evercore, J.P. Morgan and Paul, Weiss Apax’s continued request to permit an Apax fund to continue discussions with PE Firm A and Company A, including to conduct due diligence on Company A, with a view towards evaluating whether such Apax fund would be interested in potentially pursuing a strategic transaction involving the Company with PE Firm A and Company A. The Special Committee considered, among other things, the interest of the Company’s stockholders in potential counterparties having a meaningful opportunity to submit a competitive proposal for a transaction, including by having time to conduct due diligence and gain a familiarity with the Company’s business; that Apax, and if working with an Apax fund, potentially PE Firm A and Company A, had a much greater familiarity with the Company’s business than many other potential counterparties, given Apax’s history with the Company; the

restrictions on business combinations with interested stockholders of Section 203, which could apply to any potential counterparty bidding jointly with an Apax fund, unless the Board granted the counterparty a waiver in advance; and the benefits to the Company and its shareholders of the Special Committee’s process remaining confidential at that time. After consideration and deliberation, the Special Committee determined that it would continue to request that Apax refrain from having discussions with PE Firm A and Company A regarding a potential transaction, including by pausing its due diligence discussions with Company A.

During this meeting, J.P. Morgan representatives updated the Special Committee on the outreaches to potential counterparties, noting that, at the direction of the Special Committee and the Board, respectively, representatives of Evercore and of J.P. Morgan had contacted 21 financial and strategic parties. The Special Committee decided to further explore the indications of interest that the Company had received to date and commence preparation of an electronic data room (the “Data Room”) to facilitate potential counterparties’ due diligence on the Company. The Special Committee directed representatives of Evercore and of J.P. Morgan to contact one additional financial party and four additional strategic parties to assess their interest in participating in a process for a potential strategic transaction with the Company. The Special Committee further determined that it would invite certain potential counterparties, including those who had submitted preliminary indications of interest with an offer price of at least $16.00 per share (or an offer price range that included prices above $16.00 per share) of Duck Creek Common Stock, to negotiate confidentiality agreements with the Company and receive access to the Data Room, and directed representatives of Evercore and of J.P. Morgan to encourage the other parties who had submitted indications of interest to increase their offer prices.

Between December 16, 2022 and December 29, 2022, the Special Committee, with the assistance of its advisors negotiated, and the Company executed, six confidentiality agreements with potential counterparties, including with (i) Vista, (ii) PE Firm A and Company A, (iii) PE Firm E, (iv) another private equity firm (“PE Firm J”), (v) two additional private equity firms and their shared portfolio company (which we refer to collectively as “PE Firm K”) and (vi) another private equity firm (“PE Firm L”), and each of these parties and their representatives were granted access to non-public information of the Company in the Data Room and were invited to schedule diligence meetings with Company management. Each confidentiality agreement included customary standstill provisions (which standstills terminated, in accordance with their terms, upon the Company’s entry into the Merger Agreement). During this period, the Special Committee, with the assistance of its advisors, also negotiated, and the Company executed, a clean team confidentiality agreement with PE Firm A and Company A providing for special procedures for reviewing and handling competitively sensitive information of the Company provided to PE Firm A and Company A in their diligence review. Over the course of the last two weeks of December 2022, through January 8, 2023, each of the parties executing a confidentiality agreement with the Company was provided access to the documents included in the Data Room.

On December 17, 2022, representatives of PE Firm A’s legal counsel and Paul, Weiss discussed briefly the Special Committee’s process for the evaluation of a strategic transaction. PE Firm A’s legal counsel requested that the Special Committee permit an Apax fund to conduct due diligence on Company A.

On December 19, 2022, Apax’s legal counsel called Paul, Weiss to ask for an update on the process and on the Special Committee’s consideration of Apax’s request to permit an Apax fund to continue discussions and due diligence with PE Firm A and Company A. Apax’s legal counsel informed Paul, Weiss that an Apax fund had engaged a consulting firm with expertise in the Company’s industry to assist with its due diligence review of Company A, which was the same firm that had recently been engaged by the Company to assist Company management in developing some of the market-based assumptions in its drafts of the Stand-Alone Projections (“Consultant A”). Paul, Weiss representatives also relayed that the Special Committee would consider Apax’s requests again.

On December 19, 2022, PE Firm K submitted a non-binding, preliminary indication of interest for a strategic transaction involving the Company, with a preliminary offer price range of $16.00-$17.00 per share of Duck Creek Common Stock, in cash.

On December 20, 2022, PE Firm L submitted a written, non-binding, preliminary indication of interest for a strategic transaction involving the Company, with a preliminary offer price range of $16.00-$17.50 per share of Duck Creek Common Stock, in cash.

On December 20, 2022, the Special Committee held a meeting with all members of the Special Committee and representatives of each of Evercore, J.P. Morgan, Paul, Weiss and Skadden in attendance. Prior to

J.P. Morgan representatives joining the meeting, representatives of Evercore reviewed with the Special Committee Evercore’s preliminary financial analyses of the Company. After J.P. Morgan representatives joined the meeting, Evercore representatives and J.P. Morgan representatives updated the Special Committee on the status of discussions with potential counterparties and their review of the Company. J.P. Morgan representatives also advised the Special Committee that representatives of PE Firm A had informed them that PE Firm A did not require Apax as a partner for its proposal for a strategic transaction with the Company, and that PE Firm A would continue to follow the Special Committee’s requests with respect to communications with Apax.

During this meeting, Paul, Weiss representatives informed the Special Committee that Apax, through its legal counsel, notified them that an Apax fund had engaged Consultant A to conduct due diligence on Company A in its evaluation of whether such Apax fund would be interested in potentially pursuing a strategic transaction involving the Company with PE Firm A and Company A. The Special Committee considered this and decided to communicate to Apax the Special Committee’s concerns about Apax continuing to use Consultant A for this work, because Consultant A had received access to the Company’s confidential information as part of its engagement by the Company and the Special Committee believed that allowing Apax to continue to use Consultant A could give Apax an informational advantage over other potential counterparties because Consultant A was unlikely to have sufficient consultants with relevant industry experience to establish separate, dedicated teams to represent each potential counterparty to a strategic transaction involving the Company who wished to engage Consultant A to assist in its diligence of the Company.

During this meeting, representatives of Evercore and J.P. Morgan advised the Special Committee that earlier that day, Vista requested permission to share Company confidential information with three potential co-investors, and PE Firm A requested permission to share Company confidential information with a number of direct lenders. The Special Committee determined, in light of risks of premature market leaks of the process, to permit the sharing of Company confidentiality information with potential co-investors but not direct lenders at that time.

Also during this meeting, the Special Committee discussed with its advisors whether to provide the Stand-Alone Projections to potential counterparties during their due diligence. The Special Committee determined that the Stand-Alone Projections should be provided to potential counterparties, and the Stand-Alone Projections were uploaded to the Data Room shortly thereafter.

At this meeting, the Special Committee also discussed that certain potential counterparties had requested the ability under their confidentiality agreements with the Company to conduct market diligence through the use of third-party consultants, including in certain cases, Consultant A. On December 22, 2022, in response to these requests, the Special Committee determined to allow potential counterparties who had executed confidentiality agreements with the Company to conduct market diligence, but that, in light of Consultant A’s access to confidential information of the Company and the potential information advantage a party engaging Consultant A may have over parties that cannot engage Consultant A, the Special Committee would not consent to potential counterparties engaging Consultant A in connection with their evaluation of a potential transaction. The Special Committee further instructed representatives of Paul, Weiss and of Skadden to request Consultant A not accept engagements with potential counterparties relating to an evaluation of a potential transaction involving the Company.

On December 20, 2022, representatives of Apax spoke with representatives of Evercore regarding Apax’s request to be permitted to have discussions with PE Firm A and Company A.

On December 22, 2022, Apax’s legal counsel and Paul, Weiss representatives again spoke to discuss whether an Apax fund should be permitted to have access to the Data Room, to conduct due diligence on Company A, and to have discussions with PE Firm A, and representatives of Paul, Weiss confirmed that the confidentiality agreement PE Firm A and Company A entered into with the Company prohibited PE Firm A and Company A from having any discussions or other contact with Apax. Paul, Weiss representatives updated the Special Committee on this discussion, and on December 23, 2022, the Special Committee authorized Paul, Weiss to begin negotiating a letter agreement with Apax to authorize Apax to conduct due diligence on Company A, so long as such diligence would not reasonably be expected to require the Apax fund through which Apax owns Duck Creek Common Stock to file an amendment to its Schedule 13D for a period of time (the “Apax Letter Agreement”). From the period between December 23, 2022 and January 7, 2023, representatives of Apax, Evercore, J.P. Morgan, Paul, Weiss and Apax’s legal counsel communicated from time to time about Apax’s requests to permit an Apax fund to conduct due diligence on Company A and conduct discussions with PE Firm A and Company A, with a view towards evaluating whether such Apax fund would be interested in

potentially pursuing a strategic transaction involving the Company with PE Firm A and Company A. The Special Committee’s advisors kept the members of the Special Committee apprised of these negotiations, and the Special Committee discussed and directed the negotiations of the Apax Letter Agreement with its advisors.

On December 22, 2022, Mr. Jackowski and Mr. Rhodes met with representatives of PE Firm A and Company A for a management due diligence meeting. During the period between December 22, 2022 to January 2, 2023, members of Company management conducted six diligence meetings with potential counterparties and their counsel, covering an overview of the Company’s business and, to the extent requested and scheduled by the potential counterparties, additional topics including financial diligence, product and technology diligence, operations diligence and go-to-market diligence.

On December 27, 2022, Paul, Weiss delivered a draft of the Apax Letter Agreement to Apax’s legal counsel and, later that day, Apax’s legal counsel sent to Paul, Weiss a revised version reflecting Apax’s comments.

On December 30, 2022, Paul, Weiss representatives informed counsel to Apax that the Special Committee would review the revised Apax Letter Agreement the week of January 2, 2023.

On January 1, 2023, Vista inquired with J.P. Morgan representatives as to the status of the Special Committee’s process and asked for guidance on whether the terms of Vista’s preliminary indication of interest were competitive. J.P. Morgan did not tell Vista where Vista stood relative to other potential counterparties, but in response to Vista’s question, indicated that the Special Committee would consider offer price and certainty of closing in evaluating a proposal submitted by Vista relative to proposals submitted by other potential counterparties.

On January 3, 2023, the Special Committee held a meeting with all members of the Special Committee and representatives of Evercore, J.P. Morgan and Paul, Weiss in attendance. At that meeting, representatives of Evercore and J.P. Morgan reviewed with the Special Committee the outreach made to date to potential counterparties to a strategic transaction and the status of discussions with those potential counterparties, including the indications of interest received, the parties’ progress in conducting due diligence, Vista’s inquiry regarding the competitiveness of its preliminary indication of interest, and J.P. Morgan’s response to Vista’s inquiry. As of the time of this meeting, 24 potential counterparties had been contacted during the process, including 18 financial parties (including four with ownership of portfolio companies in the same industry as the Company) and six strategic parties. Of those, 13 potential counterparties had declined to continue with an evaluation of a strategic transaction, five potential counterparties showed an interest in a potential transaction but were not actively engaged in due diligence with the Company, and six potential counterparties were actively engaged in due diligence with the Company, all of which were financial parties (and in some cases, together with their portfolio companies). The Special Committee discussed with representatives of each of Evercore, J.P. Morgan and Paul, Weiss that Vista and PE Firm A had completed the most diligence of all the potential counterparties to date, and had made more progress on their diligence during the holiday period than the other potential counterparties. In light of the outstanding management diligence meetings scheduled with some potential counterparties for the weeks of January 2, 2023 and January 9, 2023, the Special Committee determined at that time that it would continue to monitor the due diligence progress of the potential counterparties and would consider, at the beginning of the week of January 9, 2023, the deadline for initial proposals that it would set.

During the meeting, the Special Committee discussed the process, risks and timing for obtaining necessary regulatory clearances for a transaction with PE Firm A and Company A, relative to a transaction with the other potential counterparties then conducting diligence on the Company, including Vista. The Special Committee directed Paul, Weiss and Skadden to begin working with legal counsel for PE Firm A and Company A on regulatory diligence and to begin negotiations with legal counsel for PE Firm A and Company A on the terms of a potential merger agreement relating to regulatory efforts standards and regulatory-related conditions to closing and termination rights. The Special Committee considered that, because Company A was a participant in the Company’s industry, a transaction with PE Firm A and Company A could potentially involve more regulatory risk or a longer time to close than transactions with the other potential counterparties.

On January 4, 2023, Paul, Weiss provided to legal counsel for Apax a further revised version of the Apax Letter Agreement and Paul, Weiss and legal counsel for Apax continued to negotiate the final terms of the Apax Letter Agreement during the period up to January 7, 2023.

On January 5, 2023, the Company announced its financial results for the fiscal quarter ended November 30, 2022. On January 5, the Company also announced that it had agreed to acquire Imburse. In light of the announcement of this acquisition, and its projected effects on the Company’s future financial results and long-term value, the Special Committee discussed the Stand-Alone Projections and the Imburse Projections (as defined in the section entitled “The Merger—Forecasts” beginning on page 68 of this Proxy Statement) with its advisors and directed the Company’s management to provide the Imburse Projections to Evercore and J.P. Morgan, and directed Evercore and J.P. Morgan to utilize both the Stand-Alone Projections and the Imburse Projections, in their updated preliminary financial analyses of the Company.

On Friday, January 6, 2023, Vista submitted a written, non-binding proposal to acquire all outstanding shares of Duck Creek Common Stock for $16.50 per share of Duck Creek Common Stock, in cash (the “$16.50 Vista Proposal”). On the same day, and prior to submitting the $16.50 Vista Proposal, representatives of Vista informed representatives of Evercore and J.P. Morgan that Vista would no longer be interested in pursuing a transaction with the Company if Vista and the Company did not finalize a definitive agreement and publicly announce a transaction by the morning of Monday, January 9, 2023.

In connection with submitting the $16.50 Vista Proposal, Vista also submitted a draft merger agreement, voting agreement, equity commitment letter and limited guarantee to the Special Committee. The $16.50 Vista Proposal stated that Vista was prepared to deliver fully committed equity financing (providing for a full equity backstop) to fund the transaction and to proceed with executing definitive agreements, that would grant the Company the right to specific performance to enforce Vista’s obligations to close; commit Vista to a “hell or high water” standard for its obligations to obtain regulatory clearances required for closing; and provide the Company a 30-day “go-shop” period after signing the merger agreement, during which the Company would be permitted to solicit and negotiate competing proposals for a strategic transaction. The $16.50 Vista Proposal provided for a termination fee payable by the Company in the event that the Company terminated the merger agreement to accept a superior proposal or in certain similar circumstances, and such termination fee would be equal to 1.6% of the equity value of the transaction if termination occurred during the go-shop period, and 3.2% of the equity value of the transaction if termination occurred after the go-shop period. As part of the $16.50 Vista Proposal, Vista contemplated that certain of the Company’s large stockholders would execute a voting agreement with Vista to support the Vista transaction.

After receiving the $16.50 Vista Proposal, the Special Committee held a meeting in the early afternoon of January 6, 2023 with all members of the Special Committee and representatives of Evercore, J.P. Morgan and Paul, Weiss in attendance. During the meeting, representatives of Evercore and of J.P. Morgan reviewed the financial aspects of the $16.50 Vista Proposal with the Special Committee and Paul, Weiss representatives reviewed with the Special Committee the key terms of the $16.50 Vista Proposal and the fiduciary duties of the members of the Special Committee under Delaware law in considering a potential transaction. The Special Committee discussed with the representatives of each of Evercore, J.P. Morgan and Paul, Weiss the conditions to completion of the $16.50 Vista Proposal, including that Vista would not require debt financing or additional equity partners in order to complete a transaction, and the “high or hell water” regulatory commitment from Vista in the draft merger agreement. The Special Committee also considered the ability for third parties to submit a superior proposal during the “go-shop” period proposed by Vista in the draft merger agreement; the broad outreach to a large number of potential counterparties that had been undertaken by representatives of Evercore and of J.P. Morgan since October 2022, at the direction of the Special Committee and of the Board, respectively; the likelihood that PE Firm A, PE Firm E, PE Firm J, PE Firm K or PE Firm L would submit a proposal with a higher offer price or higher closing certainty than the $16.50 Vista Proposal; the difference between the offer price of $16.50 per share of Duck Creek Common Stock proposed by Vista and the offer prices that such other parties had indicated to date, equity research analysts’ price targets for the Duck Creek Common Stock and the value at which the Duck Creek Common Stock was then trading; that PE Firm E, PE Firm J, PE Firm K and PE Firm L were still in early stages of their diligence review on the Company based on their progress through the Data Room and the diligence meetings they had or were then scheduled to have with the Company’s management team; the fact that, like Vista, PE Firm A had completed much more diligence on the Company than the other potential counterparties during the holiday period, and therefore that PE Firm A was likely to be able to accelerate its diligence review on the Company and potentially submit a proposal that could be competitive with the $16.50 Vista Proposal on price and contract terms on the same timeline as Vista; and the fact that Vista and

PE Firm A had each demonstrated a high level of interest in a strategic transaction with the Company and that allowing them to compete over an abbreviated timeline could provide the Company with enhanced negotiating leverage in the process and maximize the offer prices proposed by Vista and PE Firm A.

The Special Committee engaged in an extensive discussion regarding the Special Committee’s review of its strategic alternatives, including whether to inform Apax of, and solicit a proposal for a transaction from Apax and PE Firm A on, the accelerated timeframe of the $16.50 Vista Proposal and the actions the Special Committee could consider taking with the other potential counterparties engaged in the process with the Company at that time. After discussion and deliberation, the Special Committee directed representatives of Evercore and of J.P. Morgan to inform Vista that the Special Committee would be willing to consider negotiating the terms of the $16.50 Vista Proposal, and allowing Vista to preempt the broader process that the Special Committee had established, if Vista were willing to increase its offer price to a materially higher price per share of Duck Creek Common Stock. The Special Committee further directed representatives of Evercore and of J.P. Morgan to inform PE Firm A, on a no-names basis, that another potential counterparty submitted a non-binding proposal and had indicated its willingness to negotiate and execute definitive documentation and announce a transaction by January 9, 2023, that if PE Firm A were still interested in a transaction involving the Company, PE Firm A must also submit a proposal on that timeline, and that PE Firm A was competing with a proposal that had full equity financing and a “hell or high water” regulatory commitment.

At the conclusion of its meeting in the early afternoon of January 6, 2023, the Special Committee further directed Paul, Weiss to prepare a draft merger agreement to send to legal counsel for PE Firm A and Company A and to negotiate the draft with them if PE Firm A and Company A indicated they were interested in negotiating and executing definitive documentation by January 9, 2023. The Special Committee further directed Paul, Weiss and Skadden to engage with legal counsel for each of Vista and PE Firm A and Company A to conduct regulatory due diligence on a strategic transaction with each of them over the course of the weekend.

Also on January 6, 2023, representatives of Evercore and of J.P. Morgan, as directed by the Special Committee, held separate telephone conversations with representatives of PE Firm A and Vista to relay the Special Committee’s decision. Representatives of PE Firm A informed J.P. Morgan representatives that PE Firm A would assess whether it would submit a proposal for a transaction, but in the event PE Firm A decided to do so, it would not need a co-bidder in order to submit a competitive proposal and did not intend to partner with Apax in a proposal for a strategic transaction involving the Company. PE Firm A requested that the Special Committee propose an initial draft of the merger agreement. On that call, representatives of PE Firm A also requested guidance on offer price. Representatives of Evercore and of J.P. Morgan did not give a price target but told PE Firm A that they would need to put their best foot forward with respect to both price and the regulatory efforts standard in their proposed merger agreement in order to be competitive.

Later in the day on January 6, 2023, the Special Committee held another meeting at which all members of the Special Committee, except Ms. Dodd, and representatives of Evercore, J.P. Morgan, Paul, Weiss and Skadden were in attendance. Representatives of Evercore and of J.P. Morgan updated the Special Committee on their discussions with Vista and PE Firm A. During this meeting, the Special Committee directed Skadden representatives to inform the Company’s Chief Executive Officer, Chief Financial Officer and Chief Legal Officer about the $16.50 Vista Proposal and work with such management members as necessary to assist with the negotiations of the draft definitive agreements with Vista and PE Firm A and the completion of each counterparty’s confirmatory due diligence review. The Special Committee also discussed Apax’s request to continue to use Consultant A to conduct due diligence on Company A, with a separate team walled off from any Consultant A employee advising the Company and so long as Consultant A did not use or disclose any confidential information of the Company. For the reasons the Special Committee had discussed and considered in its prior meetings, the Special Committee determined that it would not be appropriate for an Apax fund to be permitted to continue to use Consultant A to conduct due diligence on Company A at this time unless a strict information wall were implemented and no employees of Consultant A that did work for the Company would be on the Consultant A team advising Apax with respect to its due diligence on Company A.

In anticipation of finalizing the Apax Letter Agreement, the Special Committee discussed with its advisors the potential timing for granting PE Firm A and Company A a waiver under Section 203. The Special Committee determined to consider and discuss the potential Section 203 waiver once the Apax Letter Agreement was finalized and ready to be executed.

On the evening of January 6, 2023, PE Firm A submitted a written, non-binding proposal to acquire all outstanding shares of Duck Creek Common Stock for $16.35 per share of Duck Creek Common Stock, in cash (the “$16.35 PE Firm A Proposal”). PE Firm A’s proposal stated that PE Firm A was prepared to deliver fully committed equity financing to fund the transaction and requested exclusivity. At the direction of the Special Committee, J.P. Morgan representatives informed PE Firm A that the offer price in the $16.35 PE Firm A Proposal was not high enough and asked PE Firm A to increase its offer price in a revised proposal.

On January 7, 2023, at the request of the Special Committee, representatives of Evercore provided further customary relationship disclosures to the Special Committee, which included disclosure of certain relationships between Evercore and its affiliates, on the one hand, and the Company, PE Firm A, Vista and their respective affiliates and portfolio companies, as applicable, on the other hand.

Also on January 7, 2023, the Special Committee held a meeting at which all members of the Special Committee and representatives of Evercore, J.P. Morgan, Paul, Weiss and Skadden were in attendance. The Special Committee discussed with the representatives of each of Evercore, J.P. Morgan, Paul, Weiss and Skadden the proposal made by PE Firm A and directed representatives of Evercore and of J.P. Morgan to continue to solicit a higher offer price from PE Firm A.

At this meeting, the Special Committee also reviewed with its advisors the terms and conditions of the $16.50 Vista Proposal, including the conditions to closing in the proposed merger agreement, the terms of the go-shop and no-shop periods included in the proposed merger agreement, the termination fees proposed in the merger agreement to be payable in the event that the Company terminated the merger agreement to accept a superior proposal, among other events, the remedies available to the Company in the event that closing conditions were satisfied but Vista did not consummate the closing, and the termination rights available to the Company and Vista under the proposed merger agreement. The Special Committee also reviewed with its advisors the terms of the draft merger agreement that Paul, Weiss was preparing to send to PE Firm A and its counsel, including the regulatory covenants included in the proposed merger agreement. The Special Committee discussed with its advisors the potential for a longer period to closing a strategic transaction with PE Firm A and Company A, relative to the anticipated period to close a transaction with Vista, because of potential additional informational requests from regulators relating to the involvement of a portfolio company in the Company’s industry. The Special Committee, following discussion with its advisors, determined that the proposed draft of the merger agreement for PE Firm A would be substantially similar to the proposed merger agreement with Vista, but that the draft agreement for PE Firm A would contain various timing and other specifically tailored regulatory-related provisions and would provide for a reverse termination fee payable by PE Firm A in the event of termination of the merger agreement for failure to obtain regulatory clearances.

On January 7, 2023, the Company and Apax finalized and executed the Apax Letter Agreement, reflecting the terms proposed by the Special Committee at its meeting earlier that day, and Apax received access to the Data Room. The Apax Letter Agreement, in its final form, permitted Apax to receive access to the Data Room, subject to confidentiality obligations, engage in co-bidding discussions with PE Firm A and Company A intended to permit the evaluation as to whether an Apax fund would be interested in potentially pursuing a strategic transaction involving the Company with PE Firm A and Company A, and conduct diligence on Company A, and provided that Apax would continue to limit its engagement of Consultant A to its evaluation of Company A, using a team that did not have confidential information of the Company and who had not worked, and would not work, on Consultant A’s engagement by the Company. The Apax Letter Agreement also prohibited Apax from taking certain actions that would reasonably be expected to require the Apax fund through which Apax owns Duck Creek Common Stock to file a Schedule 13D amendment for a period of time.

Later in the day on January 7, 2023, once the Apax Letter Agreement was confirmed by the parties and their counsel to be in final form for execution, the Special Committee discussed, and resolved by written consent to grant, a waiver to PE Firm A under Section 203. The Special Committee further granted a waiver in favor of PE Firm A and Company A of the prohibitions on co-bidding discussions in their confidentiality agreement with the Company that would permit PE Firm A and Company A to engage in discussions with Apax regarding a joint proposal for a strategic transaction involving the Company if they decided they wanted to do so. Following receipt of the Section 203 waiver and the waiver to permit co-bidding discussions under the confidentiality agreement, PE Firm A’s legal counsel stated to Paul, Weiss that PE Firm A and Company A did not wish to have discussions with Apax regarding any joint proposal for a strategic transaction at that time and intended to submit a proposal, without Apax, for negotiation and execution prior to January 9, 2023.

On January 7, 2023, Paul, Weiss sent a revised draft of the merger agreement and related documents on behalf of the Special Committee to Kirkland & Ellis LLP (“Kirkland”), Vista’s legal counsel. Later in the day on January 7, 2023, representatives of Paul, Weiss discussed via telephone with Kirkland the draft merger documents.

On January 7, 2023, Paul, Weiss also sent an initial draft of the merger agreement on behalf of the Special Committee to legal counsel for PE Firm A and Company A.

Also on January 7, 2023, a representative of Apax reiterated to J.P. Morgan representatives via a telephone call that Apax was not interested in investing in the buyer group for a strategic transaction involving the Company with any partner other than potentially PE Firm A and Company A. Separately, that day, as directed by the Special Committee, Mr. Nicoll informed Mr. Wright via a telephone call that the Special Committee had received proposals from two potential counterparties for a strategic transaction involving the Company and that the terms of both proposals were viewed by the Special Committee as attractive. Mr. Nicoll did not disclose the identity of the two potential counterparties or the terms of the proposals.

On January 7, 2023, the Company executed an engagement letter with J.P. Morgan, providing for J.P. Morgan’s engagement as financial advisor to the Company in connection with the process for a potential strategic transaction, and the Company, and the Special Committee, executed an engagement letter with Evercore, providing for Evercore’s engagement as financial advisor to the Special Committee. J.P. Morgan confirmed in its engagement letter that it had no conflicts of interest that would prevent J.P. Morgan from acting as a financial advisor to the Company in connection with a potential strategic transaction.

On January 7, 2023, the Special Committee informed Accenture plc that the Special Committee had received a proposal from Vista that it was negotiating, with the potential for finalizing and executing transaction documents in the coming days, and that Vista had requested voting agreements from the Company’s significant stockholders. The Special Committee requested that Accenture plc negotiate and execute a voting agreement with Vista (or, if the Special Committee decided to recommend a transaction with PE Firm A rather than Vista, with PE Firm A). Later that day, Accenture plc’s legal counsel informed representatives of Paul, Weiss that Accenture plc would be willing to execute a voting agreement with Vista or PE Firm A, if a transaction with either party were approved by the Special Committee. Throughout the day on January 7 and January 8, 2023, Accenture plc’s legal counsel negotiated and finalized the terms of a proposed voting agreement with Vista with Kirkland, and during the day on January 8, 2023, discussed the terms of a proposed voting agreement with PE Firm A with PE Firm A’s legal counsel.

On January 8, 2023, the Imburse Projections were uploaded to the Data Room and made available to potential counterparties for their due diligence.

On the morning of January 8, 2023, the Special Committee held a meeting with representatives of each of Paul, Weiss, Skadden, Evercore and J.P. Morgan in attendance. The Special Committee discussed the developments since the last meeting of the Special Committee in negotiations with Vista and PE Firm A, and the significant open points remaining in negotiations of the terms of the proposals and definitive agreements with each party, relating to offer price, the terms of the “go-shop” and non-solicit periods and regulatory-related covenants and related provisions. Representatives of Evercore and J.P. Morgan updated the Special Committee on the progress and engagement demonstrated by each of Vista and PE Firm A in completing their due diligence that weekend. The Special Committee directed its representatives to inform each of Vista and PE Firm A that the deadline for submitting final proposals for a strategic transaction with the Company would be 7:00 p.m., Eastern Time that day and that the Special Committee would be reconvening at 8:00 p.m., Eastern Time to consider the final proposals.

The Special Committee invited Ms. Crusco, Mr. Love, Mr. Rajasekar and Mr. Pelzer, the other members of the Board (other than the Apax nominees and Mr. Jackowski), to join the meeting. The Special Committee informed these directors of the process followed by the Special Committee and its advisors in the Special Committee’s exploration of a potential strategic transaction involving the Company, the terms and accelerated timeline of the $16.50 Vista Proposal, the terms of the $16.35 PE Firm A Proposal, and other recent events in the sales process. The Special Committee advised these directors that both Vista and PE Firm A were expected to submit revised proposals with higher offer prices later that day. Skadden representatives reviewed with all of the directors present the fiduciary duties of directors considering a change in control transaction, and reviewed with them the protocols that the Special Committee had implemented since its formation.

The Special Committee then invited Mr. Jackowski and Mr. Rhodes to join the meeting. Representatives of Evercore reviewed with the Special Committee, the additional directors (including Mr. Jackowski) and Mr. Rhodes the process undertaken by the Special Committee in evaluating a transaction, including that representatives of Evercore and of J.P. Morgan had contacted 24 parties, including 18 financial parties (including 4 with ownership of portfolio companies in the same industry as the Company) and 6 strategic parties, at the direction of the Special Committee and of the Board, respectively, the terms of the $16.50 Vista Proposal and $16.35 PE Firm A Proposal, and the diligence review in process by four other potential counterparties.

Representatives of Evercore reviewed with the Special Committee, the additional directors (including Mr. Jackowski) and Mr. Rhodes Evercore’s updated preliminary financial analyses of the Company, based on the Forecasts at the direction of the Special Committee, and the members of the Special Committee and the additional directors asked representatives of Evercore various questions about the analyses and discussed Evercore’s representatives’ answers. Representatives of J.P. Morgan then reviewed its updated preliminary financial analyses of the Company, based on the Forecasts at the direction of the Board, and the members of the Special Committee and the additional directors asked representatives of J.P. Morgan various questions about the analyses and discussed J.P. Morgan’s representatives’ answers. The members of the Special Committee and the additional directors also asked representatives of each of Evercore and J.P. Morgan questions about the differences between their respective preliminary financial analyses and the reasons for the differences in assumptions, such as discount rates, applied by each advisor. The members of the Special Committee and the additional directors also asked representatives of Paul, Weiss and Skadden questions about the terms of the $16.50 Vista Proposal and the $16.35 PE Firm A Proposal, and discussed their answers.

Throughout the day on January 8, 2023, representatives of Paul, Weiss and Skadden continued to negotiate the terms of the proposed merger agreement and other transaction documents with Kirkland and legal counsel for PE Firm A and Company A, and exchanged and discussed various drafts of the documents during the course of the day.

On January 8, 2023, at approximately 8:00 p.m., Eastern Time, the Special Committee held a meeting with all members of the Special Committee, and representatives of Evercore, J.P. Morgan, Paul, Weiss and Skadden in attendance. At the outset of the meeting, representatives of Evercore and J.P. Morgan advised the Special Committee that they had not yet received updated proposals for a strategic transaction from either Vista or PE Firm A. The Special Committee decided to reconvene after updated proposals from Vista and PE Firm A were received.

Later on January 8, 2023, after reconvening the meeting of the Special Committee, the Special Committee was informed that PE Firm A had submitted a revised written non-binding proposal, including an offer price of $18.15 per share of Duck Creek Common Stock, in cash, and shortly thereafter, PE Firm A submitted a further updated, best and final offer price of $18.66 per share of Duck Creek Common Stock, in cash (such proposal, reflecting the updated price, the “$18.66 PE Firm A Proposal”). The $18.66 PE Firm A Proposal stated that PE Firm A was prepared to deliver fully committed equity financing to fund the purchase price of the transaction; included a reverse termination fee of 6% of the equity value of the transaction in the event that the merger agreement is terminated in connection with the failure to obtain regulatory clearances prior to the outside date and a commitment from PE Firm A in the merger agreement to take all actions and agree to all remedies (except as would have a material adverse effect on the combined company) in order to obtain regulatory clearances; and required that certain parties who had recently been engaged in negotiations with the Company would be excluded from the go-shop period contemplated by the merger agreement. The $18.66 PE Firm A Proposal provided for a termination fee payable by the Company in the event that the Company terminated the merger agreement to accept a superior proposal or in certain similar circumstances, and such termination fee would be equal to 1.5% of the equity value of the transaction if termination occurred during the “go-shop” period, and 2.75% of the equity value of the transaction if termination occurred after the “go-shop” period. Shortly after submitting the $18.66 PE Firm A Proposal, PE Firm A’s legal counsel sent Paul, Weiss revised drafts of the merger agreement and other transaction documents.

Also on January 8, 2023, while the meeting of the Special Committee was in process, Vista submitted a revised written non-binding proposal, including an offer price of $19.00 per share of Duck Creek Common Stock, in cash (referred to as the “$19.00 Vista Proposal”). The $19.00 Vista Proposal was conditioned on the definitive agreements being executed within the following two hours and the execution by certain large stockholders of the Company of voting agreements in support of the transaction; stated that Vista was prepared to deliver fully committed equity financing to fund the purchase price of the transaction; included a “hell or high water” regulatory efforts covenant; required that certain parties be excluded from the “go-shop” period

contemplated by the merger agreement; and provided for a termination fee payable by the Company of 1.5% of the equity value of the transaction relating to a superior proposal during the “go-shop” period, and 3% of the equity value of the transaction for a termination relating to a superior proposal after the “go-shop” period. Concurrently with submitting the $19.00 Vista Proposal, Vista also sent the Special Committee revised drafts of the merger agreement and other transaction documents.

The Special Committee then discussed the $19.00 Vista Proposal and the $18.66 PE Firm A Proposal, including the changes agreed in the draft merger agreements with Vista and PE Firm A over the course of the day, the fact that neither counterparty would require debt financing or additional equity partners to complete a transaction, the differences in the regulatory related terms of each draft merger agreement and the regulatory-related risk profiles of the two parties in terms of certainty and timing of closing, and that both parties required certain parties to be excluded from the “go-shop” period (and subject instead to all provisions of the non-solicitation covenants beginning on the date of the Merger Agreement). The Special Committee compared the offer prices and certainty of closing in each proposal, and discussed Vista’s request that certain large stockholders of the Company execute voting agreements with Vista.

Following separate negotiations among the representatives of the legal and financial advisors for the Special Committee with the legal advisors and other representatives of Vista, and discussions of those negotiations and the items at issue with the Special Committee during the course of the ongoing meeting of the Special Committee, the Special Committee and Vista reached agreement on the final terms of the draft merger agreement, including that the merger agreement would not be conditioned on receipt of voting agreements from particular stockholders, but that the Company would use commercially reasonable efforts to enter into voting agreements with each holder of 10% or more of the Duck Creek Common Stock after signing, and that the parties that would be excluded from the “go-shop” period (and subject instead to all provisions of the non-solicitation covenants beginning on the date of the Merger Agreement) would consist of holders of 10% or more of the Company’s common stock and any party that had submitted an acquisition proposal to the Company in the previous five days. In deciding to agree to those provisions in particular, the Special Committee considered the fact that Apax had clearly stated on multiple occasions that Apax was not interested in pursuing a strategic transaction involving the Company with any partner other than PE Firm A and Company A, that PE Firm A had clearly stated on multiple occasions that it did not require a partner, including Apax, to pursue a strategic transaction involving the Company, and had subsequently stated on January 6, 2023 that it did not intend to pursue a strategic transaction involving the Company with Apax and the Special Committee’s belief that PE Firm A’s offer of $18.66 per share of Duck Creek Common Stock was “best and final”. The Special Committee further considered the fact that Accenture plc had previously informed the Special Committee that it had no interest in participating as a buyer or co-investor with a potential counterparty in a strategic transaction involving the Company, had indicated its willingness to enter into a voting agreement with the counterparty to a transaction recommended by the Special Committee, and that Accenture plc had negotiated and finalized the terms of a voting agreement with Vista.

During the meeting, representatives of Evercore reviewed with the Special Committee its financial analyses of the Company and the $19.00 Vista Proposal. The financial analyses presented by Evercore were, at the direction of the Special Committee, based on the Forecasts. Evercore delivered to the Special Committee its oral opinion, which was subsequently confirmed by delivery of a written opinion, dated January 8, 2023, and that is attached to this Proxy Statement as Annex B-2, that as of the date of such opinion and based upon and subject to the assumptions, limitations, qualifications and conditions described in Evercore’s opinion, the Merger Consideration of $19.00 per share to be received by the holders of shares of Duck Creek Common Stock in the Merger was fair, from a financial point of view, to such holders.

After discussion and deliberation, the Special Committee unanimously (i) determined that it was in the best interests of the Company and its stockholders to enter into the Merger Agreement with Vista in accordance with the terms of the $19.00 Vista Proposal and the additional terms agreed by the Special Committee and Vista, (ii) recommended that the Board approve, declare advisable and enter into the Merger Agreement and approve the execution, delivery and consummation of the merger and other transactions in accordance with the Merger Agreement and the DGCL and (iii) recommended that, subject to the approval by the Board of the Merger Agreement and the transactions contemplated thereby, the stockholders of the Company vote in favor of the adoption of the Merger Agreement and the approval of the merger and the other transactions contemplated thereby.

Immediately following the meeting of the Special Committee on January 8, 2023, the Board held a meeting with all members of the Board (other than Mr. Wright and Mr. Mackenzie) and with representatives of Evercore, J.P. Morgan, Paul, Weiss and Skadden in attendance. The Special Committee delivered its recommendation to the Board that the Board approve, declare advisable and enter into the Merger Agreement and approve the execution, delivery and consummation of the merger and other transactions in accordance with the Merger Agreement and the DGCL. Representatives of Evercore and of J.P. Morgan updated the directors on their respective financial analyses of the Company, which had been presented to the directors at the Special Committee meeting earlier that day, to take into account the $19.00 Vista Proposal. J.P. Morgan rendered to the Board its oral opinion, which was subsequently confirmed by delivery of a written opinion, dated January 9, 2023, and that is attached to this Proxy Statement as Annex B-1, that as of the date of such opinion, and based upon and subject to the assumptions made, procedures followed, and matters considered and limitations on the review undertaken by J.P. Morgan in preparing its opinion, the Merger Consideration to be paid to the stockholders of the Company pursuant to the Merger Agreement with Vista was fair, from a financial point of view, to such holders. After discussion and deliberation and based in part on the unanimous recommendation of the Special Committee, the Board (i) determined that it is in the best interests of Duck Creek and its stockholders, and declared it advisable, to enter into the Merger Agreement and consummate the Merger and the other transactions contemplated by the Merger Agreement, (ii) declared it advisable and approved and adopted the Merger Agreement, approved the execution and delivery of the Merger Agreement by the Company, the performance by the Company of its covenants and other obligations thereunder, and the consummation of the Merger and the other transactions contemplated by the Merger Agreement, including the Accenture Voting Agreement, upon the terms and conditions set forth therein and (iii) resolved to recommend that the Company stockholders vote in favor of the adoption of the Merger Agreement and the approval of the Merger and the other transactions contemplated by the Merger Agreement.

Following the meeting of the Board, representatives of Evercore and J.P. Morgan notified Vista that the Special Committee and the Board had adopted resolutions approving the Merger Agreement.

Shortly thereafter, the Company and Vista finalized and executed the Merger Agreement and other merger documentation, and Accenture plc executed a voting agreement with Vista in favor of the transactions.

At the time of the execution of the Merger Agreement, Vista had not discussed the terms of any post-closing employment or equity participation for the Company’s management with the Special Committee, the Company or any members of the Company’s management.

The following morning, on January 9, 2023, the Company issued a press release announcing the execution of the Merger Agreement.

Because Apax, PE Firm A and Company A were all deemed to be Excluded Parties under the Merger Agreement, during the week of January 9, 2023, pursuant to the terms of the Merger Agreement, the Company terminated the Data Room access of each of Apax, PE Firm A and Company A, and requested that each of them and their representatives return or destroy the confidential information of the Company that they had received during the course of their evaluation of a potential transaction.

On January 11, 2023, the Special Committee held a meeting with all members of the Special Committee and Paul, Weiss representatives in attendance. The Special Committee discussed the Company’s obligation under the Merger Agreement to use commercially reasonable efforts to enter into voting agreements with each holder of 10% or more of the Duck Creek Common Stock after signing. Accordingly, the Special Committee directed its advisors to request that Apax execute a voting agreement. Later that day, Paul, Weiss representatives informed Apax’s legal counsel of the Special Committee’s request. Between January 11, 2023 and February 17, 2023, Apax, Apax’s legal counsel, the Company, Paul, Weiss, Vista and Vista’s legal counsel discussed from time to time Apax’s willingness to enter into the voting agreement. The Apax Voting Agreement was entered into on February 17, 2023.

During the Go-Shop Period, at the direction of the Special Committee, representatives of Evercore and of J.P. Morgan contacted the potential counterparties who had been conducting diligence prior to the announcement of the Merger Agreement (other than Apax, PE Firm A and Company A) regarding their interest in pursuing an Acquisition Proposal. Each of these parties indicated that it was not interested in pursuing a strategic transaction involving the Company at that time. At the direction of the Special Committee, representatives of Evercore and of J.P. Morgan also contacted nine additional potential counterparties, including eight financial parties and one

strategic party. Of these parties, one financial party (“PE Firm M”), requested to negotiate a confidentiality agreement with the Company; however, after negotiations, PE Firm M did not enter into a confidentiality agreement with the Company and declined to continue with an evaluation of a strategic transaction.

The Go-Shop Period expired at 11:59 p.m., Eastern Time on February 7, 2023.

On January 8, 2023, the Special Committee, after considering various factors, including those described herein, and after consultation with the Special Committee’s independent legal and financial advisors, unanimously (i) determined that it is in the best interests of the Company and its stockholders, and declared it advisable, to enter into the Merger Agreement providing for the Merger in accordance with the DGCL, (ii) approved and adopted the Merger Agreement and (iii) resolved to recommend that the Board approve and adopt the Merger Agreement.

In evaluating the Merger Agreement and the transactions contemplated thereby, the Special Committee consulted with the Company’s senior management, and the legal and financial advisors of the Company and the Special Committee. In reaching its determinations and recommendations, the Special Committee considered a number of factors, including the following factors (not necessarily in order of relative importance) which the Special Committee viewed as being generally positive or favorable in coming to its determination and recommendation:

In the course of its deliberations, the Special Committee also considered a number of uncertainties, risks and other countervailing factors relating to entering into the Merger Agreement, including (not necessarily in order of relative importance):

The Special Committee concluded that the uncertainties, risks and potentially negative factors relevant to the Merger were outweighed by the potential benefits.

In addition, the Special Committee was aware of and considered the fact that some of our directors and executive officers have interests in the Merger that are different from, or in addition to, Company stockholders generally, including those interests that are a result of employment and compensation arrangements with the Company. For more information, see the section entitled “The Merger—Interests of the Directors and Executive Officers of Duck Creek in the Merger” beginning on page 72 of this Proxy Statement.

The foregoing discussion of factors considered by the Special Committee in reaching its conclusions and recommendation includes the principal factors considered by the Special Committee, but is not intended to be exhaustive and may not include all of the factors considered by the Special Committee. In light of the variety of factors considered in connection with its evaluation of the Merger Agreement and the Merger, the Special Committee did not find it practicable to, and did not, quantify or otherwise assign relative or specific weights to the specific factors considered in reaching its determinations and recommendations. Rather, the Special Committee based its decisions on the totality of the factors and information it considered. Moreover, each member of the Special Committee applied his or her own personal business judgment to the process and may have given different weight to different factors.

On January 8, 2023, the Board, after considering various factors, including those described herein, and after consultation with Duck Creek’s independent legal and financial advisors, (i) determined that it is in the best interests of the Company and its stockholders, and declared it advisable, to enter into the Merger Agreement and consummate the Merger and the other transactions contemplated by the Merger Agreement, (ii) declared it advisable and approved and adopted the Merger Agreement, approved the execution and delivery of the Merger Agreement by the Company, the performance by the Company of its covenants and other obligations thereunder, and the consummation of the Merger and the other transactions contemplated by the Merger Agreement upon the terms and conditions set forth therein and (iii) resolved to recommend that the Company stockholders vote in favor of the adoption of the Merger Agreement and the approval of the Merger and the other transactions contemplated by the Merger Agreement.

The Board recommends that you vote (i) “FOR” the proposal to adopt the Merger Agreement, thereby approving the Merger, the Merger Agreement and the other transactions contemplated thereby and (ii) “FOR” the proposal to approve, by non-binding, advisory vote, compensation that will or may be payable by Duck Creek to its named executive officers in connection with the Merger.

In evaluating the Merger Agreement and the transactions contemplated thereby, the Board consulted with the Company’s senior management, and the legal and financial advisors of the Company. In reaching its determinations and recommendations, the Board considered a number of factors, including the following factors (not necessarily in order of relative importance) which the Board viewed as being generally positive or favorable in coming to its determination and recommendation:

In the course of its deliberations, the Board also considered a number of uncertainties, risks and other countervailing factors relating to entering into the Merger Agreement, including (not necessarily in order of relative importance):

The Board concluded that the uncertainties, risks and potentially negative factors relevant to the Merger were outweighed by the potential benefits.

In addition, the Board was aware of and considered the fact that some of the Company’s directors and executive officers have interests in the Merger that are different from, or in addition to, the Company stockholders generally, including those interests that are a result of employment and compensation arrangements with the Company. For more information, see the section entitled “The Merger—Interests of the Directors and Executive Officers of Duck Creek in the Merger” beginning on page 72 of this Proxy Statement.

The foregoing discussion of factors considered by the Board in reaching its conclusions and recommendation includes the principal factors considered by the Board, but is not intended to be exhaustive and may not include all of the factors considered by the Board. In light of the variety of factors considered in connection with its evaluation of the Merger Agreement and the Merger, the Board did not find it practicable to, and did not, quantify or otherwise assign relative or specific weights to the specific factors considered in reaching its determinations and recommendations. Rather, the Board based its decisions on the totality of the factors and information it considered. Moreover, each member of the Board applied his or her own personal business judgment to the process and may have given different weight to different factors.

Pursuant to an engagement letter, the Company retained J.P. Morgan as its financial advisor in connection with the proposed Merger.

At the meeting of the Board on January 8, 2023, J.P. Morgan rendered to the Board its oral opinion to the Board, which was subsequently confirmed by delivery of a written opinion, dated as of January 9, 2023, that as of the date of such opinion, and based upon and subject to the assumptions made, procedures followed, and matters considered and limitations on the review undertaken by J.P. Morgan in preparing its opinion, the Merger Consideration to be paid to the holders of Duck Creek Common Stock in the proposed Merger was fair, from a financial point of view, to such holders.

The full text of the written opinion of J.P. Morgan, dated January 9, 2023, which sets forth, among other things, the assumptions made, procedures followed, matters considered and limitations on the review undertaken by J.P. Morgan in preparing its opinion, is attached as Annex B-1 to this Proxy Statement and is incorporated herein by reference. The summary of the opinion of J.P. Morgan set forth in this Proxy Statement is qualified in its entirety by reference to the full text of such opinion. The Company’s stockholders are urged to read the opinion in its entirety. J.P. Morgan’s opinion was addressed to the Board (in its capacity as such) in connection with and for the purposes of its evaluation of the proposed Merger, was limited to the fairness, from a financial point of view, of the consideration to be paid to the holders of Duck Creek Common Stock in the proposed Merger and did not express any opinion as to the fairness of any consideration paid in connection with the proposed Merger to the holders of any other class of securities, creditors or other constituencies of the Company or as to the underlying decision by the Company to engage in the proposed Merger. The issuance of J.P. Morgan’s opinion was approved by a fairness opinion committee of J.P. Morgan. The summary of the

opinion of J.P. Morgan set forth in this Proxy Statement is qualified in its entirety by reference to the full text of such opinion, which is attached as Annex B-1 to this Proxy Statement. The opinion does not constitute a recommendation to any stockholder of the Company as to how such stockholder should vote with respect to the proposed Merger or any other matter.

In arriving at its opinion, J.P. Morgan, among other things:

In addition, J.P. Morgan held discussions with certain members of the management of the Company with respect to certain aspects of the Merger, and the past and current business operations of the Company, the financial condition and future prospects and operations of the Company and certain other matters J.P. Morgan believed necessary or appropriate to its inquiry.

In giving its opinion, J.P. Morgan relied upon and assumed the accuracy and completeness of all information that was publicly available or was furnished to or discussed with J.P. Morgan by the Company or otherwise reviewed by or for J.P. Morgan. J.P. Morgan did not independently verify any such information or its accuracy or completeness, and, pursuant to J.P. Morgan’s engagement letter with the Company, J.P. Morgan did not assume any obligation to undertake any such independent verification. J.P. Morgan did not conduct and was not provided with any valuation or appraisal of any assets or liabilities, nor did J.P. Morgan evaluate the solvency of the Company or Parent under any state or federal laws relating to bankruptcy, insolvency or similar matters. In relying on financial analyses and forecasts provided to J.P. Morgan or derived therefrom, J.P. Morgan assumed that they were reasonably prepared based on assumptions reflecting the best currently available estimates and judgments by the Company’s management as to the expected future results of operations and financial condition of the Company to which such analyses or forecasts relate. J.P. Morgan expressed no view as to such analyses or forecasts or the assumptions on which they were based. J.P. Morgan also assumed that the Merger and the other transactions contemplated by the Merger Agreement will be consummated as described in the Merger Agreement, and that the definitive Merger Agreement will not differ in any material respects from the draft thereof furnished to J.P. Morgan. J.P. Morgan also assumed that the representations and warranties made by the Company, Parent and Merger Sub in the Merger Agreement and the related agreements were and will be true and correct in all respects material to its analysis. J.P. Morgan is not a legal, regulatory or tax expert and relied on the assessments made by advisors to the Company with respect to such issues. J.P. Morgan further assumed that all material governmental, regulatory or other consents and approvals necessary for the consummation of the Merger will be obtained without any adverse effect on the Company or on the contemplated benefits of the Merger.

J.P. Morgan’s opinion was necessarily based on economic, market and other conditions as in effect on, and the information made available to J.P. Morgan as of, the date of such opinion. J.P. Morgan’s opinion noted that subsequent developments may affect J.P. Morgan’s opinion and that J.P. Morgan does not have any obligation to update, revise or reaffirm such opinion. J.P. Morgan’s opinion is limited to the fairness, from a financial point of view, of the consideration to be paid to the holders of Duck Creek Common Stock in the proposed Merger, and J.P. Morgan has expressed no opinion as to the fairness of any consideration paid in connection with the Merger

to the holders of any other class of securities, creditors or other constituencies of the Company or as to the underlying decision by the Company to engage in the Merger. Furthermore, J.P. Morgan expressed no opinion with respect to the amount or nature of any compensation to any officers, directors or employees of any party to the Merger, or any class of such persons relative to the consideration to be paid to the holders of Duck Creek Common Stock in the Merger or with respect to the fairness of any such compensation.

The terms of the Merger Agreement, including the consideration to be paid to the holders of Duck Creek Common Stock, were determined through arm’s length negotiations between the Company and Parent, and the decision to enter into the Merger Agreement was solely that of the Special Committee and the Board. J.P. Morgan’s opinion and financial analyses were only one of the many factors considered by the Board in its evaluation of the proposed Merger and should not be viewed as determinative of the views of the Special Committee, the Board or the Company’s management with respect to the proposed Merger or the consideration, including the consideration to be paid to the holders of Duck Creek Common Stock.

In accordance with customary investment banking practice, J.P. Morgan employed generally accepted valuation methodologies in rendering its opinion to the Board on January 8, 2023, which was subsequently confirmed by delivery of a written opinion, dated as of January 9, 2023, and in the financial analyses presented to the Board on January 8, 2023 in connection with the rendering of such opinion. The following is a summary of the material financial analyses utilized by J.P. Morgan in connection with rendering its opinion to the Board and does not purport to be a complete description of the analyses or data presented by J.P. Morgan. Some of the summaries of the financial analyses include information presented in tabular format. The tables are not intended to stand alone, and in order to more fully understand the financial analyses used by J.P. Morgan, the tables must be read together with the full text of each summary. Considering the data set forth below without considering the full narrative description of the financial analyses, including the methodologies and assumptions underlying the analyses, could create a misleading or incomplete view of J.P. Morgan’s analyses.

Public Trading Multiples. Using publicly available information, J.P. Morgan compared selected financial data of the Company with similar data for selected publicly traded companies engaged in businesses that J.P. Morgan judged to be sufficiently analogous to the Company based on J.P. Morgan’s experience and its familiarity with the industries in which the Company operates. The companies selected by J.P. Morgan were as follows:

These companies selected were chosen by J.P. Morgan because they are publicly traded companies with operations and businesses that, for purposes of J.P. Morgan’s analysis, were considered similar to the Company. However, certain of these companies may have characteristics that are materially different from those of the Company. The analyses necessarily involve complex considerations and judgments concerning differences in financial and operational characteristics of the companies involved and other factors that could affect the selected companies differently than they would affect the Company.

Using publicly available information, J.P. Morgan calculated, for each selected company, the multiple of the firm value (the “FV”) (calculated as equity value, plus or minus, as applicable, net debt or net cash) to the analyst consensus estimates of calendar year 2023 revenues for the applicable company (the “FV/2023E Revenue Multiple”).

Based on the results of this analysis, J.P. Morgan selected a FV/2023E Net Revenue Multiple reference range for the Company of 4.0x to 6.5x. J.P. Morgan then applied such reference range to the Company’s projected revenue for

calendar year 2023 as set forth in the Forecasts. The analysis indicated a range of implied per share equity value for Duck Creek Common Stock (rounded to the nearest $0.10) of approximately $12.30 to $18.80, which J.P. Morgan compared to the Merger Consideration of $19.00 per share of Duck Creek Common Stock.

Selected Transactions Analysis. Using publicly available information, J.P. Morgan examined selected transactions involving businesses which J.P. Morgan judged to be sufficiently analogous to the Company’s business (or aspects thereof) based on J.P. Morgan’s experience and familiarity with the industries in which the Company operates. The following transactions were selected by J.P. Morgan as relevant to the evaluation of the proposed Merger:

None of the selected transactions reviewed was identical to the proposed Merger. However, the selected transactions were chosen by J.P. Morgan because J.P. Morgan judged certain aspects of the transactions, for purposes of J.P. Morgan’s analysis, to be similar to the proposed Merger. The analyses necessarily involve complex considerations and judgments concerning differences in financial and operational characteristics of the companies involved and other factors that could affect the transactions differently than they would affect the proposed Merger.

Using publicly available information, J.P. Morgan calculated, for each selected transaction, the multiple of the target company’s FV implied in the relevant transaction to the target company’s estimated revenue for the twelve months immediately following the announcement of the applicable transaction (the “FV/NTM Revenue Multiple”).

Based on the results of this analysis, J.P. Morgan selected a FV/NTM Revenue Multiple reference range for the Company of 4.0x to 8.5x. J.P. Morgan then applied such reference range to the Company’s projected revenue for calendar year 2023 as set forth in the Forecasts. The analysis indicated a range of implied per share equity value for Duck Creek Common Stock (rounded to the nearest $0.10) of approximately $12.30 to $24.00, which J.P. Morgan compared to the Merger Consideration of $19.00 per share of Duck Creek Common Stock.

Discounted Cash Flow Analysis. J.P. Morgan conducted a discounted cash flow analysis for the purpose of determining an implied fully diluted equity value per share for Duck Creek Common Stock. J.P. Morgan calculated the unlevered free cash flow that the Company is expected to generate from December 1, 2022 through fiscal year 2032 based upon the Forecasts, which were discussed with, and approved by, the Company for use by J.P. Morgan in connection with its financial analyses. J.P. Morgan also calculated a range of terminal values for the Company at the end of this period by applying perpetual growth rates ranging from 3.5% to 4.5%, which range was selected in consultation with Company management, to estimates of terminal revenue for the Company at the end of fiscal year 2032, based on the Forecasts. J.P. Morgan then discounted the unlevered free cash flow estimates and the range of terminal values to present value as of November 30, 2022 using discount rates ranging from 9.25% to 10.25%, which range was chosen by J.P. Morgan based upon an analysis of the weighted average cost of capital of the Company. The present values of the unlevered free cash flow estimates and the range of terminal values were then adjusted for the Company’s estimated net debt, calculated pro forma for the Company’s expected acquisition of Imburse, of $244 million as of November 30, 2022, as provided by management of the Company. This analysis indicated a range of implied per share equity value for Duck Creek Common Stock (rounded to the nearest $0.10) of $14.60 to $20.10, which J.P. Morgan compared to the Merger Consideration of $19.00 per share of Duck Creek Common Stock.

Miscellaneous. The foregoing summary of certain material financial analyses does not purport to be a complete description of the analyses or data presented by J.P. Morgan. The preparation of a fairness opinion is a complex process and is not necessarily susceptible to partial analysis or summary description. J.P. Morgan believes that the foregoing summary and its analyses must be considered as a whole and that selecting portions of the foregoing summary and these analyses, without considering all of its analyses as a whole, could create an incomplete view of the

processes underlying the analyses and its opinion. As a result, the ranges of valuations resulting from any particular analysis or combination of analyses described above were merely utilized to create points of reference for analytical purposes and should not be taken to be the view of J.P. Morgan with respect to the actual value of the Company. The order of analyses described does not represent the relative importance or weight given to those analyses by J.P. Morgan. In arriving at its opinion, J.P. Morgan did not attribute any particular weight to any analyses or factors considered by it and did not form an opinion as to whether any individual analysis or factor (positive or negative), considered in isolation, supported or failed to support its opinion. Rather, J.P. Morgan considered the totality of the factors and analyses performed in determining its opinion.

Analyses based upon forecasts of future results are inherently uncertain, as they are subject to numerous factors or events beyond the control of the parties and their advisors. Accordingly, forecasts and analyses used or made by J.P. Morgan are not necessarily indicative of actual future results, which may be significantly more or less favorable than suggested by those analyses. Moreover, J.P. Morgan’s analyses are not and do not purport to be appraisals or otherwise reflective of the prices at which businesses actually could be acquired or sold. None of the selected companies reviewed as described in the above summary is identical to the Company, and none of the selected transactions reviewed was identical to the proposed Merger. However, the companies selected were chosen by J.P. Morgan because they are publicly traded companies with operations and businesses that, for purposes of J.P. Morgan’s analysis, were considered similar to those of the Company. The transactions selected were similarly chosen by J.P. Morgan because J.P. Morgan judged certain aspects of the transactions, for purposes of J.P. Morgan’s analysis, to be similar to the proposed Merger. The analyses necessarily involve complex considerations and judgments concerning differences in financial and operational characteristics of the companies involved and other factors that could affect the companies compared to the Company and the transactions compared to the proposed Merger.

As a part of its investment banking business, J.P. Morgan and its affiliates are continually engaged in the valuation of businesses and their securities in connection with mergers and acquisitions, investments for passive and control purposes, negotiated underwritings, secondary distributions of listed and unlisted securities, private placements, and valuations for corporate and other purposes. J.P. Morgan was selected to advise the Company with respect to the proposed Merger and deliver an opinion to the Board with respect to the proposed Merger on the basis of, among other things, such experience and its qualifications and reputation in connection with such matters and its familiarity with the Company and the industries in which it operates.

For financial advisory services rendered in connection with the Merger, the Company has agreed to pay J.P. Morgan an estimated fee of approximately $21 million, $1.5 million of which became payable to J.P. Morgan at the time J.P. Morgan delivered its opinion and the remainder of which is contingent and payable upon the consummation of the proposed Merger. In addition, the Company has agreed to reimburse J.P. Morgan for certain of its expenses incurred in connection with its services, including the fees and disbursements of counsel, and will indemnify J.P. Morgan against certain liabilities arising out of J.P. Morgan’s engagement.

During the two years preceding the date of J.P. Morgan’s written opinion, J.P. Morgan and its affiliates have had commercial or investment banking relationships with the Company, for which J.P. Morgan and such affiliates have received customary compensation. Such services during such period have included acting as joint lead bookrunning manager on an offering of the Company’s equity securities in January 2021 and joint lead arranger and bookrunner on a credit facility for the Company in October 2021. During the two years preceding the date of J.P. Morgan’s written opinion, J.P. Morgan and its affiliates have also had commercial or investment banking relationships with Accenture plc, the Company’s 15.9% stockholder, for which J.P. Morgan and such affiliates have received customary compensation. Such services during such period have included acting as joint lead arranger and bookrunner on a credit facility for Accenture plc in April 2021. During the two years preceding the date of J.P. Morgan’s written opinion, J.P. Morgan and its affiliates have also had commercial or investment banking relationships with portfolio companies of Apax, the Company’s 23.8% stockholder, for which J.P. Morgan and such affiliates have received customary compensation. Such services during such period have included providing debt syndication, equity underwriting, debt underwriting and financial advisory services to portfolio companies of Apax. In addition, J.P. Morgan’s commercial banking affiliate is an agent bank and a lender under outstanding credit facilities of portfolio companies of Apax, for which it receives customary compensation or other financial benefits. During the two years preceding the date of J.P. Morgan’s written opinion, neither J.P. Morgan nor its affiliates have had any other material financial advisory or other material commercial or investment banking relationships with Parent. During the two years preceding the date of J.P. Morgan’s written opinion, J.P. Morgan and its affiliates have had commercial or investment banking relationships with

Vista, and portfolio companies of Vista, for which J.P. Morgan and such affiliates received customary compensation. J.P. Morgan’s commercial banking affiliate is an administrative agent bank and a lender under outstanding credit facilities of Vista, for which it receives customary compensation or other financial benefits. In addition, during the two years preceding the date of J.P. Morgan’s written opinion, J.P. Morgan and its affiliates have had commercial or investment banking relationships with portfolio companies of Vista for which J.P. Morgan and such affiliates have received customary compensation. Such services during such period have included providing debt syndication, equity underwriting, debt underwriting and financial advisory services to portfolio companies of Vista. J.P. Morgan’s commercial banking affiliate is an agent bank and a lender under outstanding credit facilities of portfolio companies of Vista, for which it receives customary compensation or other financial benefits. During the two-year period preceding the delivery of J.P. Morgan’s written opinion on January 9, 2023, the aggregate fees received by J.P. Morgan from the Company were approximately $8 million, from Accenture plc were approximately $7 million, from the portfolio companies of Apax were approximately $72 million and from Vista and the portfolio companies of Vista were approximately $37 million. In addition, J.P. Morgan and its affiliates hold, on a proprietary basis, less than 1% of the outstanding common stock of the Company and Accenture plc. In the ordinary course of their businesses, J.P. Morgan and its affiliates may actively trade the debt and equity securities or financial instruments (including derivatives, bank loans or other obligations) of the Company, Accenture plc, portfolio companies of Apax or portfolio companies of Vista for their own account or for the accounts of customers and, accordingly, may at any time hold long or short positions in such securities or other financial instruments.

The Special Committee retained Evercore to act as its financial advisor in connection with the Special Committee’s evaluation of strategic and financial alternatives including, but not limited to, a merger or sale of all or a majority of the equity, business or assets of the Company, regardless of the form or structure thereof, or other significant corporate transaction. As part of this engagement, the Special Committee requested that Evercore evaluate the fairness, from a financial point of view, of the Merger Consideration to be received by the holders of Duck Creek Common Stock. At a meeting of the Special Committee held on January 8, 2023, Evercore rendered to the Special Committee its opinion to the effect that, as of that date and based upon and subject to the assumptions, limitations, qualifications and conditions described in Evercore’s opinion, the Merger Consideration of $19.00 per share to be received by the holders of Duck Creek Common Stock in the Merger was fair, from a financial point of view, to such holders.

The full text of the written opinion of Evercore, dated January 8, 2023, which sets forth, among other things, the procedures followed, assumptions made, matters considered and qualifications and limitations on the scope of review undertaken in rendering its opinion, is attached as Annex B-2 to this Proxy Statement and is incorporated herein by reference. The Company encourages you to read this opinion carefully and in its entirety. Evercore’s opinion was addressed to, and provided for the information and benefit of, the Special Committee (in its capacity as such) in connection with its evaluation of the proposed Merger. The opinion does not constitute a recommendation to the Special Committee or to any other persons in respect of the Merger, including as to how any holder of shares of Duck Creek Common Stock should vote or act in respect of the Merger. Evercore’s opinion does not address the relative merits of the Merger as compared to other business or financial strategies that might be available to the Company, nor does it address the underlying business decision of the Company to engage in the Merger.

In connection with rendering its opinion Evercore, among other things:

For purposes of its analysis and opinion, Evercore assumed and relied upon the accuracy and completeness of the financial and other information publicly available, and all of the information supplied or otherwise made available to, discussed with, or reviewed by Evercore, without any independent verification of such information (and Evercore did not assume responsibility or liability for any independent verification of such information), and further relied upon the assurances of the management of the Company that they were not aware of any facts or circumstances that would make such information inaccurate or misleading. With respect to the Forecasts, Evercore assumed with the Special Committee’s consent that they had been reasonably prepared on bases reflecting the best currently available estimates and good faith judgments of management of the Company and the Special Committee as to the future financial performance of the Company and the other matters covered thereby. Evercore expressed no view as to the Forecasts or the assumptions on which they were based.

For purposes of Evercore’s analysis and opinion, Evercore assumed, in all respects material to its analysis, that the final executed Merger Agreement would not differ from the draft Merger Agreement reviewed by Evercore, that the representations and warranties of each party contained in the Merger Agreement were true and correct, that each party would perform all of the covenants and agreements required to be performed by it under the Merger Agreement and that all conditions to the consummation of the Merger would be satisfied without waiver or modification thereof. Evercore further assumed, in all respects material to its analysis, that all governmental, regulatory or other consents, approvals or releases necessary for the consummation of the Merger would be obtained without any delay, limitation, restriction or condition that would have an adverse effect on the Company or the consummation of the Merger or reduce the contemplated benefits to the holders of the Duck Creek Common Stock of the Merger. As the Special Committee was aware, the credit, financial and stock markets had been experiencing unusual volatility and Evercore expressed no opinion or view as to any potential effects of such volatility on the parties or the Merger.

Evercore did not conduct a physical inspection of the properties or facilities of the Company and did not make or assume any responsibility for making any independent valuation or appraisal of the assets or liabilities (including any contingent, derivative or other off-balance sheet assets and liabilities) of the Company, nor was Evercore furnished with any such valuations or appraisals, nor did Evercore evaluate the solvency or fair value of the Company under any state or federal laws relating to bankruptcy, insolvency or similar matters. Evercore’s opinion was necessarily based upon information made available to it as of the date of Evercore’s opinion and financial, economic, market and other conditions as they existed and as could be evaluated on the date of the opinion. It was understood that subsequent developments may affect Evercore’s opinion and that Evercore does not have any obligation to update, revise or reaffirm its opinion.

Evercore was not asked to pass upon, and expressed no opinion with respect to, any matter other than the fairness to the holders of the Duck Creek Common Stock, from a financial point of view, of the Merger Consideration. Evercore did not express any view on, and Evercore’s opinion did not address, the fairness of the proposed transaction to, or any consideration received in connection therewith by, the holders of any other class of securities, creditors or other constituencies of the Company, nor as to the fairness of the amount or nature of any compensation to be paid or payable to any of the officers, directors or employees of the Company, or any class of such persons, whether relative to the Merger Consideration or otherwise. Evercore was not asked to, nor did Evercore express any view on, and Evercore’s opinion did not address, any other term or aspect of the Merger Agreement or the Merger, including, without limitation, the structure or form of the Merger, or any term or aspect of any other agreement or instrument contemplated by the Merger Agreement or entered into or amended in connection with the Merger Agreement. Evercore’s opinion did not address the relative merits of the Merger as compared to other business or financial strategies that might be available to the Company, nor did it

address the underlying business decision of the Company to engage in the Merger. Evercore’s opinion did not constitute a recommendation to the Special Committee or to any other persons in respect of the Merger, including as to how any holder of shares of the Duck Creek Common Stock should vote or act in respect of the Merger. Evercore did not express any opinion as to the prices at which shares of Duck Creek Common Stock will trade at any time, as to the potential effects of volatility in the credit, financial and stock markets on the Company or the Merger or as to the impact of the Merger on the solvency or viability of the Company or the ability of the Company to pay its obligations when they come due. Evercore is not a legal, regulatory, accounting or tax expert and assumed the accuracy and completeness of assessments by the Company and its advisors with respect to legal, regulatory, accounting and tax matters.

Set forth below is a summary of the material financial analyses reviewed by Evercore with the Special Committee on January 8, 2023 in connection with rendering its opinion. The following summary, however, does not purport to be a complete description of the analyses performed by Evercore. The order of the analyses described and the results of these analyses do not represent relative importance or weight given to these analyses by Evercore. Except as otherwise noted, the following quantitative information, to the extent that it is based on market data, is based on market data that existed on or before January 6, 2023, and is not necessarily indicative of current market conditions.

For purposes of its analyses and reviews, Evercore considered general business, economic, market and financial conditions, industry sector performance, and other matters, as they existed and could be evaluated as of the date of its opinion, many of which are beyond the control of the Company. The estimates contained in Evercore's analyses and reviews, and the ranges of valuations resulting from any particular analysis or review, are not necessarily indicative of actual values or predictive of future results or values, which may be significantly more or less favorable than those suggested by Evercore's analyses and reviews. In addition, analyses and reviews relating to the value of companies, businesses or securities do not purport to be appraisals or to reflect the prices at which companies, businesses or securities actually may be sold. Accordingly, the estimates used in, and the results derived from, Evercore's analyses and reviews are inherently subject to substantial uncertainty.

The following summary of Evercore’s financial analyses includes information presented in tabular format. In order to fully understand the analyses, the tables should be read together with the full text of each summary. The tables are not intended to stand alone and alone do not constitute a complete description of Evercore’s financial analyses. Considering the tables below without considering the full narrative description of Evercore’s financial analyses, including the methodologies and assumptions underlying such analyses, could create a misleading or incomplete view of such analyses.

Evercore performed a discounted cash flow analysis for the purpose of determining the fully diluted equity value per share for Duck Creek Common Stock.

Using discount rates ranging from 11.0% to 13.0%, which were based on an estimate of the Company’s weighted average cost of capital, and the mid-year cash flow discounting convention, Evercore discounted to present value as of November 30, 2022, (i) estimates of Unlevered Free Cash Flow pre-NOLs (as defined in the section entitled “The Merger—Forecasts” beginning on page 68 of this Proxy Statement) that the Company was forecasted to generate during the second, third and fourth quarters of the Company’s fiscal year 2023 and the Company’s fiscal years 2024 through 2032 based on the Forecasts, and (ii) a range of terminal values for Duck Creek, which was calculated by applying perpetuity growth rates ranging from 4.0% to 6.0%, which range was selected based on Evercore’s professional judgment and experience, to estimate the terminal year unlevered, after-tax free cash flows that the Company was forecasted to generate based on the Forecasts, assuming a 22% tax rate in the second, third and fourth quarters of the Company’s fiscal year 2023 and a 24% tax rate in all fiscal years thereafter, in each case as approved by the Company’s management. Evercore derived ranges of implied total enterprise values by adding the range of present values derived above.

In calculating implied total enterprise values, Evercore included the present value of tax savings from the Company’s estimated usage of NOLs (as defined in the section entitled “The Merger—Forecasts” beginning on page 68 of this Proxy Statement) based on the Forecasts ranging between $19 million and $20 million. Based on this range of implied enterprise values, adjusted for the Company’s net debt (calculated as total debt less cash and cash equivalents, each as of November 30, 2022, less the estimated $20 million cash consideration

anticipated by the Company’s management to be paid for the acquisition of Imburse), and divided by the fully diluted shares outstanding of Duck Creek Common Stock, in each case as provided by the Company’s management, this analysis indicated a range of implied equity values per share of Duck Creek Common Stock of $10.25 to $17.15 (rounded to the nearest five cents), compared to the Merger Consideration of $19.00 per share of Duck Creek Common Stock.

Evercore reviewed and compared certain financial information of the Company to corresponding financial multiples and ratios for Guidewire Software, Inc., a selected publicly traded company in the P&C insurance industry, and for the following selected publicly traded companies in the vertical software and financial software industries (collectively, the “selected companies”), which were selected based on Evercore’s professional judgment and experience:

For each of the selected companies, Evercore calculated total enterprise value (defined as equity market capitalization plus total debt, plus preferred equity and minority interest, less cash and cash equivalents, less unconsolidated investments) as a multiple of estimated revenue for the 2023 and 2024 calendar years, which is referred to as “2023E Revenue” and “2024E Revenue”, respectively, in each case, based on closing share prices as of January 6, 2023. Estimated financial data of the selected companies were based on publicly available research analysts’ estimates.

This analysis indicated the following:

Based on the multiples it derived for the selected companies and based on its professional judgment and experience, Evercore applied a total enterprise value / revenue multiple reference range of 3.5–6.5x to the Company’s 2023E Revenue (“TEV / 2023E Revenue Reference Range”) and a total enterprise value / revenue multiple reference range of 3.0–6.0x to the Company’s 2024E Revenue (“TEV / 2024E Revenue Reference Range”), in each case, based on the Forecasts. Based on this range of implied enterprise values, the Company’s net debt (calculated as total debt less cash and cash equivalents, each as of November 30, 2022, less the estimated $20 million cash consideration anticipated by the Company’s management to be paid for the acquisition of Imburse), and the number of fully diluted shares of Duck Creek Common Stock, in each case as provided by the Company’s management, this analysis indicated a range of implied equity values per share of Duck Creek Common Stock of $10.95 to $18.80 (rounded to the nearest five cents) based on the TEV / 2023E Revenue Reference Range and a range of implied equity values per share of Duck Creek Common Stock of $10.85 to $19.95 (rounded to the nearest five cents) based on the TEV / 2024E Revenue Reference Range, in each case, compared to the Merger Consideration of $19.00 per share of Duck Creek Common Stock.

Although none of the selected companies is directly comparable to the Company, Evercore selected these companies because they are publicly traded P&C insurance, vertical software and financial software companies that Evercore, in its professional judgment and experience, considered generally relevant to the Company for purposes of its financial analyses. In evaluating the selected companies, Evercore made judgments and assumptions with regard to general business, economic and market conditions affecting the selected companies and other matters, as well as differences in the selected companies’ financial, business and operating characteristics. Accordingly, an evaluation of the results of this analysis is not entirely mathematical. Rather, this analysis involves complex considerations and judgments regarding many factors that could affect the relative values of the selected companies and the multiples derived from the selected companies. Mathematical analysis, such as determining the mean or median, is not in itself a meaningful method of using the data of the selected companies.

Evercore reviewed, to the extent publicly available, financial information related to the following selected transactions involving publicly-traded target companies in the software industry announced since 2016 that Evercore considered in its professional judgment and experience to be generally relevant for purposes of analysis, (the “selected transactions”). The selected transactions reviewed by Evercore, and the month and year each was announced, were as follows:

For each selected transaction, Evercore calculated the implied total enterprise value (defined as the target company’s implied equity value based on the consideration paid in the applicable transaction plus total debt, plus preferred equity and minority interest, less cash and cash equivalents, less unconsolidated investments) as (i) a multiple of last twelve-month (based on the last four reported quarters for each target company through the end of the last such quarter prior to the announcement of the applicable transaction) revenue for the target company at the time of the announcement of the applicable transaction, which is referred to as “LTM Revenue” and (ii) a multiple of the next twelve-month (based on the next four unreported quarters for each target company through the end of the last such quarter after the announcement of the applicable transaction) revenue, which is referred to as “NTM Revenue”. Estimated financial data of the selected transactions were based on publicly available information at the time of announcement of the relevant transaction.

Based on the multiples it derived from the selected transactions and based on its professional judgment and experience, Evercore selected (i) a reference range of total enterprise value to LTM Revenue multiples of 5.0–9.5x and applied this range of multiples to the Company’s LTM Revenue as of December 31, 2022 based on the financial results for the Company provided by the Company’s management and (ii) a reference range of total enterprise value to NTM Revenue multiples of 4.5–8.5x and applied this range of multiples to the Company’s NTM Revenue as of December 31, 2022 based on the financial results for the Company provided by the Company’s management. Based on this range of implied enterprise values, the Company’s net debt (calculated as total debt less cash and cash equivalents, each as of November 30, 2022, less the estimated $20 million cash consideration anticipated by the Company’s management to be paid for the acquisition of Imburse), and the number of fully diluted shares of Duck Creek Common Stock, in each case as provided by the Company’s management, this analysis indicated a range of implied equity values per share of Duck Creek Common Stock as shown below, compared to the Merger Consideration of $19.00 per share of Duck Creek Common Stock.

Although none of the target companies or businesses reviewed in the selected transactions analysis is directly comparable to the Company and none of the selected transactions is directly comparable to the Merger, Evercore selected these transactions based on its professional judgment and experience because they involve companies with business characteristics that for purposes of its analysis Evercore considered similar to the business characteristics of the Company. In evaluating the selected transactions, Evercore made judgments and assumptions with regard to general business, economic and market conditions and other factors existing at the time of the selected transactions, and other matters, as well as differences in financial, business and operating characteristics and other factors relevant to the target companies or businesses in the selected transactions. Accordingly, an evaluation of the results of this analysis is not entirely mathematical. Rather, this analysis involves complex considerations and judgments regarding many factors that could affect the relative values of the target companies or businesses in the selected transactions and the multiples derived from the selected transactions. Mathematical analysis, such as determining the mean or median, is not in itself a meaningful method of using the data of the selected transactions.

Evercore also noted certain other factors, which were not considered material to its financial analyses with respect to its opinion, but were referenced for informational purposes only, including, among other things, the following:

Evercore reviewed historical trading prices of shares of Duck Creek Common Stock during the twelve-month period ended January 6, 2023 noting that the low and high closing prices during such period ranged from $10.24 to $29.03 per share of Duck Creek Common Stock, respectively.

Evercore reviewed selected public market trading price targets for the shares of Duck Creek Common Stock prepared and published by equity research analysts that were publicly available as of January 6, 2023, the last full trading day prior to the delivery by Evercore of its opinion to the Special Committee. These price targets reflect analysts’ estimates of the future public market trading price of the shares of Duck Creek Common Stock at the time the price target was published. As of January 6, 2023, the range of selected equity research analyst price targets per share of Duck Creek Common Stock was $11.00 to $22.00. Public market trading price targets published by equity research analysts do not necessarily reflect current market trading prices for the shares of Duck Creek Common Stock and these target prices and the analysts’ earnings estimates on which they were based are subject to risk and uncertainties, including factors affecting the financial performance of the Company and future general industry and market conditions.

Evercore performed an illustrative analysis of the implied present value of the future price per share of Duck Creek Common Stock, which is designed to provide an indication of the present value of a theoretical future value of a company’s total enterprise value as a function of that company’s estimated revenue and its assumed total enterprise value to 2023 revenue multiple (based on the succeeding twelve-month period).

In calculating the implied present value of the future price per share of Duck Creek Common Stock, Evercore first calculated a range of implied enterprise values by multiplying estimates of the Company’s revenue based on the Forecasts for each of calendar years 2023, 2024, 2025, 2026 and 2027, by a range of total enterprise value to NTM Revenue multiples of 3.5–6.5x. This range of implied total enterprise values was then discounted back to present value using a discount rate of 12.0%, which was based on an estimate of the Company’s weighted average cost of capital. Based on this range of implied enterprise values as of today, the Company’s net debt (calculated as total debt less cash and cash equivalents, each as of November 30, 2022, less the estimated $20 million cash consideration anticipated by the Company’s management to be paid for the acquisition of Imburse) and the number of fully diluted shares of Duck Creek Common Stock, in each case as provided by the Company’s management, this analysis indicated a range of implied present prices per share of Duck Creek Common Stock of $10.95 to $23.10 (rounded to the nearest five cents), compared to the Merger Consideration of $19.00 per share of Duck Creek Common Stock.

Using publicly available information, Evercore reviewed the 15 transactions outlined above under Selected Transaction Analysis. Using publicly available information, Evercore calculated the premiums paid as the percentage by which the per share consideration paid or proposed to be paid in each such transaction exceeded the unaffected closing market prices per share of the target companies prior to announcement of each transaction.

Based on the results of this analysis and its professional judgment and experience, Evercore applied a premium range of 30.0% to 75.0% to the closing price per share of Duck Creek Common Stock of $12.99 as of January 6, 2023. This analysis indicated a range of implied equity values per share of Duck Creek Common Stock of $16.90 to $22.75 (rounded to the nearest five cents), compared to the Merger Consideration of $19.00 per share of Duck Creek Common Stock.

Evercore made certain assumptions for an acquisition of the Company via a leveraged buyout (“LBO”), based on its experience and professional judgment, including assuming (i) a 15.0–25.0% required rate of return for the LBO acquirer, (ii) a holding period of 5.75 years, (iii) an exit multiple of 4.5– 6.5x NTM Revenue and (iv) assumed leverage equal to 2.0x estimated average recurring revenue as of February 28, 2023, to derive a range of implied equity values per share of Duck Creek Common Stock. This analysis indicated an implied equity value range of $11.50 to $22.05 per share of Duck Creek Common Stock (rounded to the nearest five cents).

The foregoing summary of Evercore’s financial analyses does not purport to be a complete description of the analyses or data presented by Evercore to the Special Committee. In connection with the review of the Merger by the Special Committee, Evercore performed a variety of financial and comparative analyses for purposes of rendering its opinion. The preparation of a fairness opinion is a complex process and is not necessarily susceptible to partial analysis or summary description. Selecting portions of the analyses or of the summary described above, without considering the analyses as a whole, could create an incomplete view of the processes underlying Evercore’s opinion. In arriving at its fairness determination, Evercore considered the results of all the analyses and did not draw, in isolation, conclusions from or with regard to any one analysis or factor considered by it for purposes of its opinion. Rather, Evercore made its determination as to fairness on the basis of its professional judgment and experience after considering the results of all the analyses. In addition, Evercore may have given various analyses and factors more or less weight than other analyses and factors, and may have deemed various assumptions more or less probable than other assumptions. As a result, the ranges of valuations resulting from any particular analysis or combination of analyses described above should not be taken to be the view of Evercore with respect to the actual value of the shares of Duck Creek Common Stock. Rounding may result in total sums set forth in this section not equaling the total of the figures shown.

Evercore prepared these analyses for the purpose of providing an opinion to the Special Committee as to the fairness, from a financial point of view, of the Merger Consideration to the holders of shares of Duck Creek Common Stock. These analyses do not purport to be appraisals or to necessarily reflect the prices at which the business or securities actually may be sold. Any estimates contained in these analyses are not necessarily indicative of actual future results, which may be significantly more or less favorable than those suggested by such estimates. Accordingly, estimates used in, and the results derived from, Evercore’s analyses are inherently subject to substantial uncertainty, and Evercore assumes no responsibility if future results are materially different from those forecasted in such estimates.

Evercore’s financial advisory services and its opinion were provided for the information and benefit of the Special Committee (in its capacity as such) in connection with its evaluation of the proposed Merger. The issuance of Evercore’s opinion was approved by an Opinion Committee of Evercore.

Evercore did not recommend any specific amount of consideration to the Special Committee, the Board or the Company’s management or that any specific amount of consideration constituted the only appropriate consideration in the Merger for the holders of Duck Creek Common Stock.

Pursuant to the terms of Evercore’s engagement letter with the Special Committee, the Company has agreed to pay Evercore a fee for its services in the amount of approximately $21.3 million, of which $1.5 million came due upon delivery of Evercore’s opinion, and the balance of which will be payable contingent upon the consummation of the Merger. The Company has also agreed to reimburse Evercore for its expenses and to indemnify Evercore against certain liabilities arising out of its engagement.

During the two year period prior to the date of its opinion, Evercore and its affiliates were not engaged to provide financial advisory or other services to the Company and Evercore did not receive any compensation from the Company during such period. During the two year period prior to the date of its opinion, Evercore and its affiliates provided financial advisory services to Vista (“Sponsor”), an affiliate of Parent, and its affiliates and portfolio companies for which Evercore received fees for the rendering of these services in the amount of approximately $17.6 million. During the two year period prior to the date of its opinion, Evercore and its affiliates provided financial advisory services regarding matters unrelated to the Company to Apax, an affiliate of which owns more than 5% of the Duck Creek Common Stock, and its affiliates and portfolio companies for which Evercore received fees for the rendering of these services in the amount of approximately $16.6 million. During the two year period prior to the date of its opinion, Evercore and its affiliates did not provide financial advisory services to Accenture LLP and Accenture Holdings BV (“Accenture”), which owns more than 5% of the Duck Creek Common Stock. Evercore may provide financial advisory or other services to the Company, Sponsor, Apax, Accenture or any of their respective affiliates or portfolio companies in the future, and in connection with any such services Evercore may receive compensation.

Evercore and its affiliates engage in a wide range of activities for its and their own accounts and the accounts of customers, including corporate finance, mergers and acquisitions, equity sales, trading and research, private equity, placement agent, asset management and related activities. In connection with these businesses or

otherwise, Evercore and its affiliates and/or its or their respective employees, as well as investment funds in which any of them may have a financial interest, may at any time, directly or indirectly, hold long or short positions and may trade or otherwise effect transactions for their own accounts or the accounts of customers, in debt or equity securities, senior loans and/or derivative products or other financial instruments of or relating to the Company, Sponsor, Apax, Accenture or potential parties to the Merger and/or any of their respective affiliates or portfolio companies or persons that are competitors, customers or suppliers of the Company, Sponsor, Apax, Accenture or any of their respective affiliates or portfolio companies.

The Special Committee engaged Evercore to act as a financial advisor based on Evercore’s qualifications, experience and reputation. Evercore is an internationally recognized investment banking firm and regularly provides fairness opinions to its clients in connection with mergers and acquisitions, leveraged buyouts and valuations for corporate and other purposes.

In connection with Duck Creek’s review of strategic alternatives, Duck Creek management prepared unaudited forecasted financial information of Duck Creek for fiscal year 2023 through fiscal year 2027 (the “Stand-Alone Projections”), which were reviewed by the Board, subsequently approved by the Board on December 5, 2022, and then used by the Board in connection with its review of strategic alternatives. The Stand-Alone Projections were made available to potential counterparties to a strategic transaction, including Vista, in connection with their due diligence review of a potential transaction. The Stand-Alone Projections were prepared from October through early December 2022 and the Board approved the Stand-Alone Projections on December 5, 2022.

This Proxy Statement contains certain non-GAAP financial measures, including:

Duck Creek believes that its presentation of these non-GAAP measures provides useful supplemental information to investors and management regarding Duck Creek’s financial condition and results of operations. Other firms may calculate non-GAAP measures differently than Duck Creek, which limits comparability between companies. Non-GAAP measures are not in accordance with, or a substitute for, GAAP.

Although the information in the Stand-Alone Projections is presented with numerical specificity, it reflects numerous estimates and assumptions made by Duck Creek management with respect to industry performance, general business, economic, regulatory, market and financial conditions and other future events, as well as matters specific to Duck Creek’s business in each case as of the date it was prepared, all of which are difficult or impossible to predict accurately and many of which are beyond the Company’s control. Certain key material assumptions underlying the Stand-Alone Projections include the following:

The following table presents a summary of the Stand-Alone Projections:

On January 5, 2023, a subsidiary of the Company entered into a share purchase agreement to acquire IMburse AG (together with its subsidiaries, “Imburse”), and the acquisition was completed on January 25, 2023. In December 2022, in connection with the evaluation by Duck Creek management of the acquisition of Imburse, Duck Creek management prepared unaudited forecasted financial information of Imburse for fiscal year 2023 through fiscal year 2027 (the “Imburse Projections”). The Imburse Projections treat Imburse on a stand-alone basis without giving effect to the Merger. The Imburse Projections were made available to potential counterparties to a strategic transaction, including Vista, in connection with their due diligence review of a potential transaction.

Although the information in the Imburse Projections is presented with numerical specificity, it reflects numerous estimates and assumptions made by Duck Creek management with respect to industry performance, general business, economic, regulatory, market and financial conditions and other future events, as well as matters specific to Imburse’s business, in each case as of the date it was prepared, all of which are difficult or impossible to predict accurately and many of which are beyond the Company’s control. Certain key material assumptions underlying the Imburse Projections include the following:

The following table presents a summary of the Imburse Projections:

The projections summarized in the table below for the Company’s second through fourth fiscal quarters 2023 through fiscal year 2032 (the “Forecasts”) were prepared on the following basis:

Although the information in the table below is presented with numerical specificity, it reflects numerous estimates and assumptions made with respect to industry performance, general business, economic, regulatory, market and financial conditions and other future events, as well as matters specific to Duck Creek’s business, in each case as of the date it was prepared, all of which are difficult or impossible to predict accurately and many of which are beyond the Company’s control.

The Stand-Alone Projections, the Imburse Projections and the Forecasts treat Duck Creek on a stand-alone basis without giving effect to, and as if Duck Creek never contemplated, the Merger, including the impact of negotiating or executing the Merger Agreement, the expenses that may be incurred in connection with consummating the Merger, the effect of any business or strategic decision or action that has been or will be taken as a result of the Merger Agreement having been executed or the effect of any business or strategic decisions or actions which would likely have been taken if the Merger Agreement had not been executed but which were instead altered, accelerated, postponed or not taken in anticipation of the Merger.

The Stand-Alone Projections, the Imburse Projections and the Forecasts were not prepared with a view toward public disclosure and the summary thereof is included in this Proxy Statement only because (i) the Stand-Alone Projections were made available to the Board in connection with its review of strategic alternatives, (ii) the Stand-Alone Projections and the Imburse Projections were made available to potential counterparties to a strategic transaction, including Vista, in connection with their due diligence review of a potential transaction, and (iii) the Forecasts were used by JPM for purposes of preparing its financial analyses and fairness opinion

provided to the Board and by Evercore for purposes of preparing its financial analyses and fairness opinion provided to the Special Committee, each on January 8, 2023, as described in the section entitled “The Merger—Opinions of Duck Creek’s Financial Advisors” beginning on page 55 of this Proxy Statement. The summary of the Stand-Alone Projections, the Imburse Projections and the Forecasts is not being included in this Proxy Statement to influence your decision whether to vote for the proposal to adopt the Merger Agreement. The Stand-Alone Projections, the Imburse Projections and the Forecasts were not prepared with a view toward compliance with the published guidelines established by the SEC or the American Institute of Certified Public Accountants for preparation or presentation of prospective financial information, or GAAP (and do not include footnote disclosures as may be required by GAAP). Neither KPMG LLP, Duck Creek’s independent registered public accounting firm (“KPMG”), nor any other audit firm has audited, reviewed, examined, compiled or applied agreed-upon procedures with respect to the Stand-Alone Projections, the Imburse Projections or the Forecasts and, accordingly, KPMG has not expressed an opinion or any other form of assurance with respect thereto. The KPMG report included in Duck Creek’s Annual Report on Form 10-K for the year ended August 31, 2022, which is incorporated by reference into this Proxy Statement, relates to Duck Creek’s historical financial information and does not extend to the Stand-Alone Projections, the Imburse Projections or the Forecasts and should not be read to do so.

The Stand-Alone Projections, the Imburse Projections and the Forecasts are subject to estimates and assumptions in many respects and, as a result, subject to interpretation and reflect subjective judgment in many respects, and, therefore, are susceptible to multiple interpretations and periodic revisions based on actual results and business developments. While presented with numerical specificity, the Stand-Alone Projections, the Imburse Projections and the Forecasts are based upon a variety of estimates and assumptions that are inherently uncertain, though considered reasonable by Duck Creek management as of the date of their preparation. These estimates and assumptions may prove to be inaccurate for any number of reasons, which are difficult to predict and which are beyond Duck Creek’s control, including general economic conditions, competition and the risks discussed in this Proxy Statement under the section entitled “Cautionary Statement Regarding Forward-Looking Statements” beginning on page 22 of this Proxy Statement. The Stand-Alone Projections, the Imburse Projections and the Forecasts also reflect assumptions as to certain business decisions that are subject to change. Because the Stand-Alone Projections, the Imburse Projections and the Forecasts cover multiple years, by their nature, they become subject to greater uncertainty with each successive year and are unlikely to anticipate each and every circumstance that could have an effect on Duck Creek’s business and its results of operations. There can be no assurance that the projections contained in the Stand-Alone Projections, the Imburse Projections and the Forecasts will be realized, and actual results may differ materially from those shown therein.

The information in the Stand-Alone Projections, the Imburse Projections and the Forecasts is not factual and should not be relied upon as being necessarily indicative of future results. The inclusion of the summary of the Stand-Alone Projections, the Imburse Projections and the Forecasts in this Proxy Statement should not be regarded as an indication that Duck Creek or anyone else then considered, or now considers, such summaries to be necessarily predictive of actual future events, and this information should not be relied upon as such. In light of the foregoing, Duck Creek’s stockholders are cautioned not to place undue reliance thereon. The Stand-Alone Projections, the Imburse Projections and the Forecasts should be evaluated, if at all, in conjunction with the historical financial statements and other information regarding Duck Creek contained in Duck Creek’s public filings with the SEC.

None of Duck Creek, its financial advisors or its or their respective affiliates, advisors, officers, directors or other representatives can provide any assurance that actual results will not differ from the Stand-Alone Projections, the Imburse Projections or the Forecasts, and none of them undertakes any obligation to update, or otherwise revise or reconcile, the Stand-Alone Projections, the Imburse Projections or the Forecasts to reflect circumstances existing after the date the Stand-Alone Projections, the Imburse Projections or the Forecasts were generated or to reflect the occurrence of future events even in the event that any or all of the assumptions underlying the Stand-Alone Projections, the Imburse Projections or the Forecasts, as applicable, are shown to be in error. Since the date of the Stand-Alone Projections, the Imburse Projections and the Forecasts, Duck Creek has made publicly available its actual results of operations for the first quarter of fiscal year 2023, ended November 30, 2022. You should review Duck Creek’s Quarterly Report on Form 10-Q filed with the SEC on January 9, 2023 for information about Duck Creek’s actual results of operations for the fiscal quarter ended November 30, 2022. Duck Creek does not intend to make publicly available any update or other revision to the Stand-Alone Projections, the Imburse Projections or the Forecasts, even in the event that any or all assumptions

are shown to be in error. Except as required by applicable law, none of Duck Creek, its financial advisors or its or their respective affiliates, advisors, officers, directors or other representatives has made or makes any representation to any Company stockholder or any other person (including Vista, in the Merger Agreement or otherwise) regarding the Stand-Alone Projections, the Imburse Projections or the Forecasts, Duck Creek’s ultimate performance compared to the information contained therein or that forecasted results will be achieved.

In considering the recommendation of the Board that holders of Duck Creek Common Stock vote to adopt the Merger Agreement, our stockholders should be aware that certain of Duck Creek’s non-employee directors and executive officers have interests in the Merger that are different from, or in addition to, those of Duck Creek’s stockholders generally. The Board was aware of and considered these interests, among other matters, in approving the Merger Agreement and the Merger, and in recommending that the Merger Agreement be adopted by Company stockholders.

As of February 21, 2023, Duck Creek’s directors and executive officers (including individuals who have been a director or executive officer since the beginning of the last fiscal year), as a group, hold 3,155,880 shares of Duck Creek Common Stock, excluding any unvested Company RSAs.

At the Effective Time, each share of Duck Creek Common Stock outstanding as of immediately prior to the Effective Time that is held by Duck Creek’s directors and executive officers will be cancelled and extinguished and automatically converted into the right to receive cash in an amount equal to $19.00, without interest.

As of February 21, 2023, certain of our directors and executive officers (including individuals who have been a director or executive officer since the beginning of the last fiscal year) held unvested Company RSAs and Company Options, as set forth in the tables below.

Each Company RSA held by a director or executive officer that is outstanding as of immediately prior to the Effective Time will be fully vested, cancelled and automatically converted into the right to receive an amount in cash equal to (A) the number of shares of Duck Creek Common Stock subject to such Company RSA, multiplied by (B) $19.00, subject to any required withholding of Taxes. Notwithstanding the foregoing, the cash amount relating to each Company RSA granted after January 8, 2023 will not be fully vested and will instead remain subject to the same terms and conditions and be paid out on the same vesting schedule as applied to such Company RSA prior to the Effective Time, subject to the holder’s continued employment or service through the applicable vesting date. None of our directors or executive officers have been granted any Company RSAs on or after January 8, 2023.

Each Company Option held by a director or executive officer will be cancelled immediately upon the Effective Time without payment or consideration.

See the section entitled “Interests of the Directors and Executive Officers of Duck Creek in the Merger—Golden Parachute Compensation” beginning on page 75 of this Proxy Statement for an estimate of the amounts that would become payable to each Duck Creek named executive officer in respect of his or her unvested Company RSAs.

Each of our executive officers is party to a written employment arrangement with Duck Creek Technologies LLC, a subsidiary of Duck Creek, pursuant to which the executive officer will receive the following severance payments and benefits upon a termination of the executive officer’s employment without cause or, in the case of Messrs. Jackowski, Rhodes and Van Biert, resignation for good reason (as defined in the applicable employment agreement) following the consummation of the Merger, subject to each executive officer’s execution of a general release of claims:

Each of our executive officers has also entered into a restrictive covenants agreement with Duck Creek Technologies LLC, which provides that, during the course of each executive officer’s employment and for the one-year period following termination of his or her employment for any reason, each executive officer will not compete with, or solicit any vendors, customers, suppliers, employees, consultants or agents of, Duck Creek Technologies LLC or its affiliates. The restrictive covenants agreement further provides that each executive officer may not disclose any proprietary, trade secret or confidential information involving Duck Creek Technologies LLC or its affiliates and will assign all applicable intellectual property rights to them.

The Merger Agreement provides that the Surviving Corporation and its subsidiaries will (and Parent will cause the Surviving Corporation and its subsidiaries to) honor and fulfill, in all respects, the obligations of Duck Creek and its subsidiaries pursuant to any indemnification agreements with employees and indemnified persons, which are any of their current or former directors or officers (and any person who becomes a director or officer of Duck Creek or any of its subsidiaries prior to the Effective Time), for any acts or omissions by such indemnified persons or employees occurring prior to the Effective Time. In addition, during the period commencing at the Effective Time and ending on the sixth anniversary of the Effective Time, the Surviving Corporation and its subsidiaries will (and Parent will cause the Surviving Corporation and its subsidiaries to) cause the certificates of incorporation, bylaws, and other similar organizational documents of the Surviving Corporation and its subsidiaries to contain provisions with respect to indemnification, exculpation and the advancement of expenses that are at least as favorable as the indemnification, exculpation and advancement of expenses provisions set forth in the certificate of incorporation, bylaws and other similar organizational documents of the subsidiaries of Duck Creek, as applicable, as of the date of the Merger Agreement. During such six-year period, such provisions may not be repealed, amended or otherwise modified in any adverse manner except as required by applicable law.

In addition, the Merger Agreement provides that, during the six-year period commencing at the Effective Time, the Surviving Corporation will (and Parent will cause the Surviving Corporation to) indemnify and hold harmless each current or former director or officer of Duck Creek and its subsidiaries (and any person who becomes a director or officer of Duck Creek or any of its subsidiaries prior to the Effective Time), to the fullest extent permitted by law or pursuant to any indemnification agreements with Duck Creek and its subsidiaries in effect on the date of the Merger Agreement, from and against all costs, fees and expenses (including attorneys’ fees and investigation expenses), judgments, fines, losses, claims, damages, liabilities and amounts paid in settlement or compromise in connection with any legal proceeding arising, directly or indirectly, out of or pertaining, directly or indirectly, to (1) any action or omission, or alleged action or omission, in such indemnified person’s capacity as an affiliate, director, officer, employee or agent of Duck Creek, its subsidiaries or their affiliates to the extent that such action or omission, or alleged action or omission, occurred prior to or at the Effective Time; and (2) the Merger, as well as any actions taken by Duck Creek or its subsidiaries or the Buyer Parties with respect thereto. The Merger Agreement also provides that Duck Creek and its subsidiaries will advance all fees and expenses (including fees and expenses of any counsel) as incurred by any such indemnified person in the defense of such legal proceeding.

The Merger Agreement also provides that Duck Creek may purchase a prepaid “tail” policy from an insurance carrier with the same or better credit rating as Duck Creek’s directors’ and officers’ liability insurance carrier on the date of the Merger Agreement on terms (including with respect to coverage, conditions, retentions, limits and amounts) that are no less favorable than those of Duck Creek’s directors’ and officers’ liability insurance policies as in effect on the date of the Merger Agreement, subject to certain limits on the aggregate cost for such “tail” policy. The “tail” policy will cover claims arising from facts, events, acts or omissions that occurred at or prior to the Effective Time, including the transactions contemplated in the Merger Agreement.

In addition, without limiting the foregoing, the Merger Agreement requires Parent to cause the Surviving Corporation to maintain, on terms no less advantageous to the indemnified parties, Duck Creek’s directors’ and officers’ insurance policies for a period of at least six years commencing at the Effective Time. Neither Parent nor the Surviving Corporation will be required to pay premiums for such policy or the “tail” policy to the extent such premiums exceed, on an annual basis, 300% of the aggregate annual premiums currently paid by Duck Creek, and if the premium for such insurance coverage would exceed such amount Parent shall be obligated to cause the Surviving Corporation to obtain the greatest coverage available for a cost not exceeding such amount.

As of the date of this Proxy Statement, none of our executive officers has had any discussions or negotiations, or entered into any agreement, with Parent or any of its affiliates regarding the potential terms of their individual employment arrangements or the right to purchase or participate in the equity of Parent or one or more of its affiliates following the consummation of the Merger. Prior to or following the consummation of the Merger, however, certain executive officers may have discussions, or may enter into agreements with, Parent, the Company or their respective affiliates regarding employment with, or the right to purchase or participate in the equity of, Parent or one or more of its affiliates after the Effective Time.

In accordance with Item 402(t) of Regulation S-K, the table below sets forth the compensation that is based on or otherwise relates to the Merger that may be paid or become payable to each of our named executive officers in connection with the Merger. Please see the previous portions of this section for further information regarding this compensation.

The amounts indicated in the table below are estimates of the amounts that would be payable assuming, solely for purposes of this table, that the Merger is consummated on February 21, 2023, and in the case of each named executive officer, that the named executive officer’s employment is terminated by the Surviving Corporation without cause, or if applicable, by the named executive officer for good reason, in each case, on that date.

In addition to the assumptions regarding the consummation date of the Merger and the termination of employment, these estimates are based on certain other assumptions that are described in the footnotes accompanying the table below. Accordingly, the ultimate values to be received by a named executive officer in connection with the Merger may differ from the amounts set forth below.

The obligation of the Buyer Parties to consummate the Merger is not subject to any financing condition.

We anticipate that the total amount of funds necessary to pay the aggregate Merger Consideration payable to the Company stockholders in the Merger is approximately $2.65 billion in cash.

In connection with the financing of the Merger, Vista Fund VIII and Parent have entered into an Equity Commitment Letter, pursuant to which Vista Fund VIII has agreed to provide Parent with an equity commitment of up to approximately $2.65 billion in cash, which will be available, together with cash on hand at Duck Creek as of the Closing, to fund the aggregate Merger Consideration payable to the Company stockholders (including payments in respect of our outstanding equity-based awards payable in connection with the Closing pursuant to the Merger Agreement) and to pay the fees, expenses and other amounts required to be paid in connection with the Closing by Duck Creek and the Buyer Parties.

The Equity Commitment Letter provides, among other things, that: (1) Duck Creek is an express third-party beneficiary thereof in connection with Duck Creek’s exercise of its rights related to specific performance under the Merger Agreement; and (2) Vista Fund VIII will not oppose the granting of an injunction, specific performance or other equitable relief in connection with the exercise of such third-party beneficiary rights. The Equity Commitment Letter may not be waived, amended or modified except by a written instrument signed by Parent and Vista Fund VIII.

Pursuant to the Limited Guarantee, Vista Fund VIII has agreed to guarantee the due and punctual payment to Duck Creek of all of the liabilities and obligations of the Buyer Parties under the Merger Agreement (the “Guaranteed Obligations”).

The obligations of Vista Fund VIII under the Limited Guarantee are subject to an aggregate cap equal to the Parent Liability Limitation.

Subject to specified exceptions, the Limited Guarantee will terminate upon the earliest of:

The Closing will take place no later than the second (2^nd) business day following the satisfaction or waiver of all conditions to the Closing (described below under the section entitled, “Terms of the Merger Agreement—Conditions to the Closing of the Merger” beginning on page 95 of this Proxy Statement) (other than those conditions to be satisfied at the Closing) or such other time agreed to in writing by Parent and Duck Creek.

The Merger will be accounted for as a “purchase transaction” for financial accounting purposes.

The following discussion is a summary of certain U.S. federal income tax consequences of the Merger that may be relevant to U.S. Holders and Non-U.S. Holders (each as defined below) whose shares of Duck Creek Common Stock are converted into the right to receive cash pursuant to the Merger. This discussion is based upon the Internal Revenue Code of 1986, as amended (the “Code”), Treasury Regulations promulgated under the Code, court decisions, published positions of the Internal Revenue Service (the “IRS”), and other applicable authorities, all as in effect on the date of this Proxy Statement and all of which are subject to change or to differing interpretations at any time, possibly with retroactive effect.

This discussion is limited to Company stockholders who hold their shares of Duck Creek Common Stock as “capital assets” within the meaning of Section 1221 of the Code (generally, property held for investment purposes). In addition, this summary does not describe any tax consequences arising under the laws of any state, local or foreign jurisdiction and does not consider any aspects of U.S. federal tax law other than income taxation (e.g., estate or gift taxation) or the alternative minimum tax or the Medicare net investment income surtax that may be relevant or applicable to a particular holder in connection with the Merger. For purposes of this discussion, a “holder” means either a U.S. Holder or a Non-U.S. Holder (each as defined below) or both, as the context may require.

This discussion is for general information purposes only and does not address all of the tax consequences that may be relevant to holders in light of their particular circumstances nor does it address any consequences to holders subject to special rules under U.S. federal income tax law, including, for example:

If a partnership (including an entity or arrangement, domestic or non-U.S., treated as a partnership for U.S. federal income tax purposes) is a beneficial owner of shares of Duck Creek Common Stock, then the tax treatment of a partner in such partnership will generally depend upon the status of the partner and the activities of the partner and the partnership. Partnerships holding shares of Duck Creek Common Stock and partners therein should consult their tax advisors regarding the consequences of the Merger.

No ruling has been or will be sought from the IRS regarding the U.S. federal income tax consequences of the Merger described herein. No assurance can be given that the IRS will agree with the views expressed herein, or that a court will not sustain any challenge by the IRS in the event of litigation.

THIS DISCUSSION IS PROVIDED FOR GENERAL INFORMATION ONLY AND DOES NOT CONSTITUTE LEGAL ADVICE TO ANY HOLDER. IT IS NOT INTENDED TO CONSTITUTE A COMPLETE ANALYSIS OR DESCRIPTION OF ALL POTENTIAL U.S. FEDERAL INCOME TAX CONSEQUENCES RELATING TO THE MERGER. HOLDERS SHOULD CONSULT THEIR OWN TAX ADVISORS CONCERNING THE U.S. FEDERAL INCOME TAX CONSEQUENCES RELATING TO THE MERGER IN LIGHT OF THEIR PARTICULAR CIRCUMSTANCES AND ANY CONSEQUENCES UNDER STATE, LOCAL, NON-U.S. OR OTHER TAX LAWS.

For purposes of this discussion, a “U.S. Holder” is a beneficial owner of shares of Duck Creek Common Stock who or that is for U.S. federal income tax purposes:

The receipt of cash by a U.S. Holder in exchange for shares of Duck Creek Common Stock pursuant to the Merger will be a taxable transaction for U.S. federal income tax purposes. Such U.S. Holder’s gain or loss generally will be equal to the difference, if any, between the amount of cash received and the U.S. Holder’s adjusted tax basis in the shares surrendered pursuant to the Merger. A U.S. Holder’s adjusted tax basis generally will equal the amount that such U.S. Holder paid for the shares. Such gain or loss generally will be capital gain or loss and will be long-term capital gain or loss if such U.S. Holder’s holding period in such shares is more than one (1) year at the time of the completion of the Merger. A reduced tax rate on capital gain generally will apply to long-term capital gain of a non-corporate U.S. Holder (including individuals). The deductibility of capital losses is subject to limitations. If a U.S. Holder acquired different blocks of common stock at different times or different prices, such U.S. Holder must determine its tax basis, holding period, and gain or loss separately with respect to each block of common stock.

For purposes of this discussion, the term “Non-U.S. Holder” means a beneficial owner of Duck Creek Common Stock that is neither a U.S. Holder nor a partnership for U.S. federal income tax purposes.

Subject to the discussion under “Information Reporting and Backup Withholding” below, any gain realized by a Non-U.S. Holder pursuant to the Merger generally will not be subject to U.S. federal income tax unless:

Non-U.S. Holders should consult their tax advisors regarding the tax consequences to them of the Merger.

Information reporting and backup withholding (currently, at a rate of twenty-four percent (24%)) may also apply to the proceeds received by a holder pursuant to the Merger. Backup withholding generally will not apply to (1) a U.S. Holder that furnishes a correct taxpayer identification number and certifies that such holder is not subject to backup withholding on IRS Form W-9 (or a substitute or successor form) or (2) a Non-U.S. Holder that (i) provides a certification of such Non-U.S. Holder’s foreign status on an applicable IRS Form W-8 (or a

substitute or successor form) or (ii) otherwise establishes an exemption from backup withholding. Backup withholding is not an additional tax. Any amounts withheld under the backup withholding rules may be refunded or credited against the holder’s U.S. federal income tax liability; provided that the holder timely furnishes the required information to the IRS.

THE FOREGOING SUMMARY DOES NOT DISCUSS ALL ASPECTS OF U.S. FEDERAL INCOME TAXATION THAT MAY BE RELEVANT TO PARTICULAR HOLDERS. IT IS FOR GENERAL INFORMATION ONLY AND IS NOT TAX ADVICE. HOLDERS ARE URGED TO CONSULT THEIR TAX ADVISORS AS TO THE PARTICULAR TAX CONSEQUENCES TO THEM OF THE RECEIPT OF CASH FOR THEIR SHARES OF DUCK CREEK COMMON STOCK PURSUANT TO THE MERGER UNDER ANY U.S. FEDERAL, STATE, FOREIGN, LOCAL OR OTHER TAX LAWS, OR UNDER ANY APPLICABLE INCOME TAX TREATY.

Duck Creek and the Buyer Parties have agreed to use reasonable efforts to take all actions necessary to comply with all regulatory notification requirements, and to obtain all regulatory approvals required to consummate the Merger and the other transactions contemplated by the Merger Agreement. These approvals include approval under, or notifications pursuant to, the HSR Act and any other applicable antitrust laws (whether domestic or foreign).

Under the HSR Act and the rules promulgated thereunder, the Merger cannot be completed until Duck Creek and Vista Fund VIII file a notification and report form with the Federal Trade Commission (the “FTC”) and the Antitrust Division of the Department of Justice (the “DOJ”) under the HSR Act and the applicable waiting period has expired or been terminated. A transaction notifiable under the HSR Act may not be completed until the expiration of a thirty (30) calendar day waiting period following the parties’ filing of their respective HSR Act notification forms or the early termination of that waiting period. Duck Creek and Vista Fund VIII made the necessary filings with the FTC and the Antitrust Division of the DOJ on January 18, 2023. The waiting period under the HSR Act expired at 11:59 p.m. Eastern Time on February 17, 2023.

At any time before or after the consummation of the Merger, notwithstanding the termination of the waiting period under the HSR Act, the FTC or the Antitrust Division of the DOJ could take such action under the antitrust laws as it deems necessary or desirable in the public interest, including seeking to enjoin the completion of the Merger, seeking divestiture of substantial assets of the parties or requiring the parties to license, or hold separate, assets or terminate existing relationships and contractual rights. At any time before or after the completion of the Merger, and notwithstanding the termination of the waiting period under the HSR Act, any state could take such action under the antitrust laws as it deems necessary or desirable in the public interest. Such action could include seeking to enjoin the completion of the Merger or seeking divestiture of substantial assets of the parties. Private parties may also seek to take legal action under the antitrust laws under certain circumstances.

On February 17, 2023, a purported stockholder of Duck Creek filed the O’Dell Complaint, naming as defendants Duck Creek and each member of the Board. On February 22, 2023 a purported stockholder of Duck Creek filed the Reddiar Complaint, naming as defendants Duck Creek and each member of the Board. On February 22, 2023 a purported stockholder of Duck Creek filed the Dangerfield Complaint, naming as defendants Duck Creek and each member of the Board. On February 23, 2023 a purported stockholder of Duck Creek filed the Powell Complaint, naming as defendants Duck Creek and each member of the Board.

The Complaints allege, among other things, that the defendants violated Section 14(a) and Section 20(a) of the Exchange Act and also that the Board breached its fiduciary duties. Specifically, one or more of the Complaints allege that the Preliminary Proxy Statement contains materially incomplete and misleading representations and information concerning the Company’s financial forecasts, the financial analyses conducted by J.P. Morgan and Evercore in support of their respective fairness opinions, the scope of the non-disclosure agreements entered into between Duck Creek and potential bidders in connection with a potential strategic transaction involving Duck Creek and potential conflicts of interests of certain insiders of Duck Creek. The relief sought in one or more of the Complaints includes enjoining the consummation of the Merger unless and until the defendants disclose certain allegedly material information, rescinding, to the extent already implemented, the Merger Agreement or any of the terms thereof, granting rescissory damages, directing the defendants to

disseminate a proxy statement that does not contain any untrue statements of material fact and that states all required or necessary material facts, directing the defendants to account for all alleged damages suffered as a result of the defendants’ alleged wrongdoing, declaring that defendants violated Sections 14(a) and/or 20(a) of the Exchange Act as well as Rule 14a-9 promulgated thereunder, and awarding the plaintiffs their respective costs and disbursements, including reasonable attorneys’ and experts’ fees and expenses.

Duck Creek believes that the Complaints are without merit and Duck Creek and the individual defendants intend to defend against the Complaints; however, Duck Creek cannot predict the amount of time and expense that will be required to resolve the Complaints, nor the outcomes thereof.

The outcome of any pending or future litigation is uncertain. Such litigation, if not resolved, could prevent or delay consummation of the Merger and result in substantial costs to Duck Creek, including any costs associated with the indemnification of directors and officers. One of the conditions to the consummation of the Merger is that no temporary restraining order, preliminary or permanent injunction or other judgment or order issued by any court of competent jurisdiction or other legal or regulatory restraint or prohibition preventing the consummation of the Merger will be in effect, nor will any action have been taken by any governmental authority (as defined in the Merger Agreement) of competent jurisdiction, and no statute, rule, regulation or order will have been enacted, entered enforced or deemed applicable to the Merger that, in each case, prohibits, makes illegal or enjoins the consummation of the Merger. Therefore, if a plaintiff were successful in obtaining an injunction prohibiting the consummation of the Merger on the agreed-upon terms, then such injunction may prevent the Merger from being consummated, or from being consummated within the expected time frame.

The discussion of the terms of the Merger Agreement in this section and elsewhere in this Proxy Statement is qualified in its entirety by reference to the complete text of the Merger Agreement, a copy of which is attached as Annex A to this Proxy Statement and is incorporated into this Proxy Statement by reference. This summary does not purport to be complete and may not contain all of the information about the Merger that is important to you. You are encouraged to read the Merger Agreement carefully and in its entirety as it is the legal document that governs the Merger.

The following description of the Merger Agreement does not purport to be complete and is qualified in its entirety by reference to the full text of the Merger Agreement, which is included as Annex A hereto. The Merger Agreement has been included to provide Company stockholders with information regarding its terms. It is not intended to provide any other factual information about Duck Creek, Parent, Merger Sub, Vista or their respective subsidiaries or affiliates. The representations, warranties and covenants contained in the Merger Agreement were made only for purposes of the Merger Agreement as of the specific dates therein, were solely for the benefit of the parties to the Merger Agreement, may be subject to limitations agreed upon by the contracting parties, including being qualified by confidential disclosures made for the purposes of allocating contractual risk among the parties to the Merger Agreement instead of establishing these matters as facts, and may be subject to standards of materiality applicable to the contracting parties that differ from those applicable to Company stockholders. Company stockholders should not rely on the representations, warranties and covenants or any descriptions thereof as characterizations of the actual state of facts or condition of the parties thereto or any of their respective subsidiaries or affiliates. Moreover, information concerning the subject matter of representations and warranties may change after the date of the Merger Agreement, which subsequent information may or may not be reflected in Duck Creek’s public disclosures. Accordingly, the representations, warranties, covenants and other agreements in the Merger Agreement should not be read alone, and you should read the information provided elsewhere in this document and in our filings with the SEC regarding Duck Creek and its business. Please see the section entitled “Where You Can Find More Information” beginning on page 112 of this Proxy Statement.

The Merger Agreement provides that, upon the terms and subject to the conditions of the Merger Agreement, and in accordance with the DGCL, at the Effective Time, Merger Sub will be merged with and into Duck Creek, whereupon the separate corporate existence of Merger Sub will thereupon cease, and Duck Creek will continue as the Surviving Corporation. As a result of the Merger, the Surviving Corporation will become a wholly owned subsidiary of Parent and Duck Creek Common Stock will no longer be publicly traded. In addition, Duck Creek Common Stock will be delisted from Nasdaq and deregistered under the Exchange Act, in each case, in accordance with applicable laws, rules and regulations, and Duck Creek will no longer file periodic reports with the SEC on account of Duck Creek Common Stock. If the Merger is consummated, you will not own any shares of capital stock of the Surviving Corporation. The Effective Time will occur upon the filing of a certificate of merger with, and the acceptance for record of such filing by, the Secretary of State of the State of Delaware (or at such later time as Duck Creek and the Buyer Parties may agree and specify in the certificate of merger).

The Closing will take place no later than the second (2^nd) business day following the satisfaction or waiver (to the extent permitted under the Merger Agreement) of all conditions to the Closing (described in the section entitled, “Terms of the Merger Agreement—Conditions to the Closing of the Merger” beginning on page 95 of this Proxy Statement) (other than those conditions to be satisfied at the Closing, but subject to the satisfaction or waiver (to the extent permitted in the Merger Agreement) of such conditions) or such other time agreed to in writing by Parent and Duck Creek. On the date on which the Closing actually occurs (the “Closing Date”), the parties will file a certificate of merger with the Secretary of State for the State of Delaware as provided under the DGCL. The Merger will become effective upon the filing and acceptance for record of the certificate of merger, or such later time as may be agreed by the parties and specified in the certificate of merger.

From and after the Effective Time, Duck Creek, as the Surviving Corporation in the Merger, will possess all properties, rights, privileges, powers and franchises of Duck Creek and Merger Sub, and all of the debts, liabilities and duties of Duck Creek and Merger Sub will become the debts, liabilities and duties of the Surviving Corporation.

At the Effective Time, the board of directors of the Surviving Corporation will consist of the directors of Merger Sub as of immediately prior to the Effective Time, each to hold office in accordance with the certificate of incorporation and bylaws of the Surviving Corporation until their respective successors are duly elected or appointed and qualified, and the officers of Merger Sub as of immediately prior to the Effective Time will be the officers of the Surviving Corporation, until their successors are duly appointed. At the Effective Time, the certificate of incorporation of Duck Creek as the Surviving Corporation will be amended and restated in its entirety to read substantially identically to the certificate of incorporation of Merger Sub as in effect immediately prior to the Effective Time, and the bylaws of Merger Sub, as in effect immediately prior to the Effective Time, will become the bylaws of the Surviving Corporation, until thereafter amended in accordance with the applicable provisions of the DGCL and such certificate of incorporation of the Surviving Corporation and such bylaws.

Upon the consummation of the Merger, each share of Duck Creek Common Stock outstanding as of immediately prior to the Effective Time (other than the Owned Company Shares or the Dissenting Company Shares, as applicable) will be cancelled and extinguished and automatically converted into the right to receive the Per Share Price (or in the case of a lost, stolen or destroyed certificate, upon delivery of an affidavit (and bond, if required) in accordance with the Merger Agreement). Each Owned Company Share will be cancelled and extinguished without any conversion thereof or consideration paid therefor.

After the Merger is completed, Company stockholders will have the right to receive the Per Share Price, but Company stockholders will no longer have any rights as a stockholder of Duck Creek (except that Company stockholders who properly exercise their appraisal rights may have the right to receive payment for the “fair value” of their shares determined pursuant to an appraisal proceeding, as contemplated by Delaware law). For more information, please see the section entitled “Appraisal Rights” beginning on page 106 of this Proxy Statement.

Company RSAs. At the Effective Time, each Company RSA, whether vested or unvested, that is outstanding as of immediately prior to the Effective Time will be fully vested, cancelled and automatically converted into the right to receive an amount in cash equal to the product of (A) the number of shares of Duck Creek Common Stock subject to such Company RSA, multiplied by (B) $19.00, subject to any required withholding of Taxes. Notwithstanding the foregoing, the cash amount relating to each Company RSA that was granted after January 8, 2023 will not be fully vested and will instead remain subject to the same terms and conditions and be paid out on the same vesting schedule as applied to such Company RSA prior to the Effective Time, subject to the holder’s continued employment or service through the applicable vesting date.

Company RSUs. At the Effective Time, each Company RSU, whether vested or unvested, that is outstanding as of immediately prior to the Effective Time will be fully vested, cancelled and automatically converted into the right to receive an amount in cash equal to the product of (A) the number of shares of Duck Creek Common Stock subject to such Company RSU, multiplied by (B) $19.00, subject to any required withholding of taxes. Notwithstanding the foregoing, the cash amount relating to each Company RSU that was granted after January 8, 2023 will not be fully vested and will instead remain subject to the same terms and conditions and be paid out on the same vesting schedule as applied to such Company RSU prior to the Effective Time, subject to the holder’s continued employment or service through the applicable vesting date.

Company Phantom Stock Awards. At the Effective Time, each Company Phantom Stock Award, whether vested or unvested, that is outstanding as of immediately prior to the Effective Time will be fully vested, cancelled and automatically converted into the right to receive an amount in cash equal to the product of (A) the number of shares of Duck Creek Common Stock measured by reference to such Company Phantom Stock Award, multiplied by (B) $19.00, subject to any required withholding of taxes.

Company Options and Company SARs. At the Effective Time, each Company Option and Company SAR will be cancelled immediately upon the Effective Time without payment or consideration.

Prior to the Closing, Parent will designate a bank or trust company reasonably acceptable to Duck Creek to act as the paying agent for the Merger (the “Payment Agent”) and to make payments of the Merger Consideration to Company stockholders. At or prior to the Closing, Parent will deposit (or cause to be deposited) with the Payment Agent an amount of cash sufficient to pay the aggregate Merger Consideration; provided that Duck Creek shall, at the written request of Parent, and, if requested by Parent, in exchange for a promissory note issued by Parent to the Company, the amount and terms of which shall be reasonably determined by Parent, deposit with the Payment Agent at the Closing such portion of such aggregate Merger Consideration from the Company’s Cash on Hand (as defined in the Merger Agreement) as specified in such request.

Promptly following the Closing (and in any event within three (3) business days), the Payment Agent will send to each holder of record of shares of Duck Creek Common Stock as of immediately prior to the Effective Time (A) a letter of transmittal in customary form (which will specify that delivery will be effected, and risk of loss and title to the certificates representing such shares (the “Certificates”) will pass, only upon delivery of the Certificates to the Payment Agent) and (B) instructions for use in effecting the surrender of the shares of Duck Creek Common Stock represented by the Certificates and book-entry shares, as applicable, in exchange for the Per Share Price.

If any cash deposited with the Payment Agent is not claimed within one (1) year following the Closing Date, such cash will be returned to the Parent, upon demand, and any holders of Duck Creek Common Stock who have not complied with the exchange procedures in the Merger Agreement will thereafter look only to the Parent as general creditor for payment of the Per Share Price (subject to applicable law). Any cash deposited with the Payment Agent that remains unclaimed two (2) years following the Closing Date will, to the extent permitted by applicable law, become the property of the Surviving Corporation free and clear of any claims or interest of any person previously entitled thereto.

The Merger Agreement contains representations and warranties of the Company and the Buyer Parties.

Some of the representations and warranties in the Merger Agreement made by Duck Creek are qualified as to materiality or Company Material Adverse Effect. For purposes of the Merger Agreement, “Company Material Adverse Effect” means, with respect to Duck Creek, any change, event, violation, inaccuracy, effect or circumstance (each, an “Effect”) that, individually or taken together with all other Effects that have occurred on or prior to the date of determination of the occurrence of the Company Material Adverse Effect, is or would reasonably be expected to have a material adverse effect on the business, financial condition or results of operations of the Company and its subsidiaries, taken as a whole; provided, however, that none of the following (by itself or when aggregated) will be deemed to be or constitute a Company Material Adverse Effect or will be taken into account when determining whether a Company Material Adverse Effect has occurred or may, would or could occur (subject to the limitations set forth below):

In the Merger Agreement, the Company made customary representations and warranties to the Buyer Parties that are subject, in some cases, to specified exceptions and qualifications contained in the Merger Agreement. These representations and warranties relate to, among other things: