Guidewire Software : 2023 Proxy Statement

2023

Proxy Statement and Annual Report

Guidewire is the platform P&C insurers trust to engage, innovate, and grow efficiently. We combine digital, core, analytics, and machine learning to deliver our platform as a cloud service.

Tuesday,

December 19, 2023

1:30 P.M. Pacific Time

Online only via live audio webcast

Your vote is important.

Whether or not you plan to attend the annual meeting, we hope that you will vote as soon as possible. You may vote your shares over the Internet or, if you receive printed proxy materials, you may vote by a toll free telephone number, over the Internet, or by completing, signing, dating, and returning your proxy card or voting instruction card in the envelope provided. Any stockholder attending the annual meeting may vote by Internet during the meeting, even if you have already returned a proxy card or voting instruction card.

GUIDEWIRE SOFTWARE, INC. 970 Park Pl, Suite 200, San Mateo, California 94403

Notice of Annual Meeting of Stockholders

To Our Stockholders:

You are cordially invited to attend the 2023 annual meeting of stockholders of Guidewire Software, Inc. (the "Company") to be held on Tuesday, December 19, 2023, at 1:30 p.m. Pacific Time. The 2023 annual meeting of stockholders will be held via live audio webcast at www.virtualshareholdermeeting.com/GWRE2023.

We are holding the annual meeting for the following purposes:

1. To elect eight directors to serve for one-year terms expiring at the 2024 annual meeting of stockholders;
2. To ratify the appointment of KPMG LLP as our independent registered public accounting firm for the fiscal year ending July 31, 2024;
3. To conduct a non-binding, advisory vote to approve the compensation of our named executive officers;
4. To approve the amendment and restatement of the Guidewire Software, Inc. Amended and Restated 2020 Stock Plan; and
5. To transact such other business as may properly come before the annual meeting or at any and all adjournments, continuations or postponements thereof.

If you owned our common stock at the close of business on October 23, 2023, you may attend and vote at the annual meeting.

On or about November 2, 2023, we expect to mail to our stockholders a Notice of Internet Availability of Proxy Materials containing instructions on how to access our Proxy Statement and 2023 Annual Report on Form 10-K.

Our Proxy Statement and 2023 Annual Report on Form 10-K can also be accessed directly at www.proxyvote.com using the 16-digit control number located on your proxy card or in the instructions accompanying your proxy materials.

Thank you for your ongoing support of Guidewire.

Sincerely,

MIKE ROSENBAUM

Chief Executive Officer

San Mateo, California November 2, 2023

Table of Contents

Proxy Summary	i
General Information	1
Questions and Answers About the Annual	1
Meeting, the Proxy Materials and Voting Your
Shares
Proposal One: Election of Directors	7
Proposal Two: Ratification of Appointment of	14
Independent Registered Public Accounting Firm
Audit Committee Report	15
Proposal Three: Non-Binding, Advisory Vote on	16
Compensation of Named Executive Officers
Proposal Four: Amendment and Restatement of	17
the Guidewire Software, Inc. Amended and
Restated 2020 Stock Plan
Information About the Board and Corporate	25
Governance
Meetings of the Board	26
Stockholder Communications with the Board	26
Code of Business Conduct and Ethics	26
Independence of the Board	26
Structure of the Board	26
Executive Sessions	27
Director Attendance at Annual Stockholder	27
Meetings
Board's Role in Risk Oversight	27
Compensation Plans Risk Assessment	27
Whistleblower Procedures	28
Committees of the Board	29
Consideration of Director Nominees	31
Corporate Sustainability and Environmental,	32
Social, and Governance Matters
Executive Officers	35
Information Regarding Compensation of	37
Directors and Executive Officers
Director Compensation Table	37
Stock Ownership Guidelines	39

Compensation Committee Interlocks and Insider	39
Participation
Compensation Committee Report	40
Compensation Discussion and Analysis	41
Executive Compensation Philosophy and	41
Objectives
Compensation Program Design	42
Compensation-Setting Process	42
Executive Compensation Program Elements	45
Executive Agreements and Termination of	51
Employment Arrangements
Other Compensation Policies	52
Tax and Accounting Considerations	54
Summary Compensation Table	55
Grants of Plan-Based Awards	56
Outstanding Equity Awards at Fiscal Year End	58
Options Exercises and Stock Vested During	60
Fiscal Year 2023
Post-Employment Compensation	61
Potential Payments Upon Termination or	62
Change In Control
CEO Pay Ratio	64
Pay Versus Performance	65
Ownership of Guidewire Software, Inc. Common	70
Stock
Certain Relationships and Related Party	72
Transactions
Transactions with Our Executive Officers and	72
Directors
Policies and Procedures for Related Party	73
Transactions
Additional Information	74
Appendix A: Non-GAAP Financial Measures	A-1
Appendix B: Proposed Amended and Restated	B-1
2020 Stock Plan

Ways to Vote

Proxy Summary

The information provided in this Proxy Summary is for your convenience only and is merely a summary of the information contained in this proxy statement. You should read this entire proxy statement carefully.

Voting is important. Please find here the many different ways you can submit your vote.

By Written Proxy: Stockholders of record can vote their shares by marking, signing, and timely returning the enclosed proxy card. Beneficial owners must follow the directions provided by their broker, bank, or other nominee in order to direct such broker, bank, or nominee as to how to vote their shares.

By Telephone and Internet before the annual meeting: Stockholders of record who received printed proxy materials can vote their shares by telephone at 1-800-690-6903until 11:59 p.m. Eastern Time on December 18, 2023 or via the Internet at www.proxyvote.com 24 hours a day, seven days a week, until 11:59 p.m. Eastern Time on December 18, 2023, in each case by using the 16- digit control number, which is on the proxy card or in the instructions accompanying the proxy materials. Beneficial owners may also vote by telephone or the Internet before the annual meeting by using the 16-digitcontrol number, which is on the proxy card.

By Internet during the annual meeting: Stockholders of record may vote by Internet during the annual meeting at www.virtualshareholder meeting.com/GWRE2023.

Beneficial owners may also vote by Internet during the annual meeting at www.virtualshareholdermeeting. com/GWRE2023.

Instructions on how to attend and vote during the annual meeting are described at www.proxyvote.com. Stockholders will need their 16-digitcontrol number which is on the proxy card or in the instructions accompanying the proxy materials in order to vote.

Voting Recommendations

The following table sets forth the recommendations of our board of directors ("Board") in respect of each of the proposals to be presented to our stockholders at the annual meeting, as well as the applicable voting requirement for each of such proposals:

				Page
Proposal	Board Recommendation	Reference
1	Election of directors	FOR	Majority of the votes cast	Page
7
2	Ratification of appointment of independent registered public	FOR	Majority of the shares	Page
accounting firm	represented	14

• Non-bindingadvisory vote to approve the compensation of the Company's named executive officers

• Amendment and restatement of the Guidewire Software, Inc. Amended and Restated 2020 Stock Plan

FOR	Majority of the shares	Page
represented	16
FOR	Majority of the shares	Page
represented	17

Guidewire Software, Inc.

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2023 Proxy Statement

Our Board of Directors

						Committees
		Director				Nominating and
Name	Age	Since	Independent	Audit	Compensation	Corporate Governance	Risk
Marcus S. Ryu	50	2001
Co-Founder and Chairman
Paul Lavin	61	2014
Lead Independent Director
Mike Rosenbaum	52	2019
Chief Executive Officer
David S. Bauer	63	2022
Margaret Dillon	64	2019
Michael C. Keller	63	2019
Lead Customer Advocate
Catherine P. Lego	67	2019
Rajani Ramanathan	56	2021

Chairperson Member

Guidewire Software, Inc.

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2023 Proxy Statement

GUIDEWIRE SOFTWARE, INC.

Proxy Statement for the

2023 Annual Meeting of Stockholders

General Information

Our Board is soliciting proxies for our 2023 annual meeting of stockholders to be held on Tuesday, December 19, 2023 at 1:30 p.m. Pacific Time via audio webcast at: www.virtualshareholdermeeting.com/GWRE2023.

The Notice of Internet Availability of Proxy Materials containing instructions on how to access our proxy statement for the 2023 annual meeting of stockholders and our Annual Report on Form 10-K for the fiscal year ended July 31, 2023 (the "2023 Annual Report"), which includes our audited consolidated financial statements, is first being mailed on or about November 2, 2023, to stockholders entitled to vote at the annual meeting. We have also made these materials available on our website at www.guidewire.com under "About/Investor Relations" on or about November 2, 2023.

This proxy statement contains important information for you to consider when deciding how to vote on the matters brought before the 2023 annual meeting of stockholders. Please read it carefully. Unless the context requires otherwise, the words "Guidewire," "we," the "Company," "us," and "our" refer to Guidewire Software, Inc.

Questions and Answers About the Annual Meeting, the Proxy Materials, and Voting Your Shares

Why did I receive a Notice of Internet Availability of Proxy Materials instead of a full set of proxy materials?

We have elected to furnish our proxy materials, including our proxy statement for the 2023 annual meeting of stockholders and our 2023 Annual Report, primarily via the Internet. The Notice of Internet Availability of Proxy Materials is being provided in accordance with Securities and Exchange Commission ("SEC") rules and contains instructions on how to access our proxy materials. Stockholders may request to receive all future proxy materials in printed form by mail or electronically by e-mail by following the instructions contained in the Notice of Internet Availability of Proxy Materials. We encourage stockholders to take advantage of the availability of our proxy materials on the Internet to help reduce the environmental impact and cost of our annual meetings of stockholders.

What items will be voted on at the annual meeting?

There are four items expected to be voted on at the annual meeting:

1. The election of eight directors to serve for one-year terms expiring at the 2024 annual meeting;
2. The ratification of the appointment of KPMG LLP as our independent registered public accounting firm for the fiscal year ending July 31, 2024;
3. The non-binding, advisory vote to approve the compensation of our named executive officers; and
4. The amendment and restatement of the Guidewire Software, Inc. Amended and Restated 2020 Stock Plan.

What are our Board's voting recommendations?

Our Board recommends that you vote your shares "FOR" each of the nominees to the Board, "FOR" the ratification of the appointment of KPMG LLP, "FOR" the approval of the compensation of our named executive officers, and "FOR" the amendment and restatement of the Guidewire Software, Inc. Amended and Restated 2020 Stock Plan.

Guidewire Software, Inc.

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2023 Proxy Statement

What is a proxy?

Our Board is soliciting your vote at our 2023 annual meeting of stockholders. A proxy is your legal designation of another person to vote the stock you own. That other person is called a proxy. If you designate someone as your proxy in a written document, that document also is called a proxy or a proxy card. You may designate as your proxies Mike Rosenbaum, Jeff Cooper, and Winston King, who have been selected by our Board to serve as proxies for our 2023 annual meeting of stockholders.

Who can vote at the annual meeting?

The record date for our 2023 annual meeting of stockholders is October 23, 2023. The record date was established by our Board. Stockholders of record at the close of business on the record date are entitled to:

• Receive notice of the annual meeting; and
• Vote by written proxy, Internet or telephone before the annual meeting or by Internet during the annual meeting.

On the record date, 81,930,494 shares of our common stock were outstanding. Each stockholder is entitled to one vote for each share of common stock held on the record date.

What do I need in order to attend the annual meeting online?

We will be hosting our annual meeting via live webcast only. Any stockholder can attend the annual meeting of stockholders live online at www.virtualshareholdermeeting.com/GWRE2023. The webcast will start at 1:30 p.m. Pacific Time on December 19, 2023. Stockholders may vote and ask questions while attending the annual meeting online. In order to be able to attend the annual meeting, you will need the 16-digit control number, which is on your proxy card or in the instructions accompanying your proxy materials. Instructions on how to participate in the annual meeting of stockholders are also posted online at www.proxyvote.com.

Why is this annual meeting being held virtually?

We are excited to provide ease of access, real-time communication, and cost savings for our stockholders. We believe that hosting a virtual meeting provides easy access for our stockholders and facilitates participation since stockholders can participate from any location around the world. You will be able to participate in the annual meeting online and submit your questions during the meeting by visiting www.virtualshareholdermeeting.com/GWRE2023.

How can I submit a question at the annual meeting?

If you would like to submit a question during the annual meeting, log into www.virtualshareholdermeeting.com/GWRE2023 by using the 16-digit control number, which is on your proxy card or in the instructions accompanying your proxy materials, type your question into the "Ask a Question" field, and click "Submit." Questions pertinent to meeting matters will be read and answered during the meeting, subject to time constraints. The questions and answers will be available as soon as practicable after the annual meeting at www.virtualshareholdermeeting.com/GWRE2023 and will remain available for one week after posting.

What if I have technical difficulties or trouble accessing the annual meeting?

If you encounter any technical difficulties with accessing the audio webcast on the meeting day, please call the technical support number that will be posted on www.virtualshareholdermeeting.com/GWRE2023. Technical support will be available starting at 1:00 p.m. Pacific Time, 30 minutes before the meeting start time, on December 19, 2023, and will remain available until the annual meeting has ended.

Is my vote confidential?

Proxy instructions, ballots, and voting tabulations that identify individual stockholders are handled in a manner that protects your voting privacy. Your vote will not be disclosed either among our employees or to third parties, except: (1) as necessary to meet applicable legal requirements, (2) to allow for the tabulation of votes and certification of the vote, and (3) to facilitate a successful proxy solicitation. Occasionally, stockholders provide written comments on their proxy card, which are then forwarded to our management.

Guidewire Software, Inc.

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2023 Proxy Statement

What is the difference between holding shares as a "stockholder of record" and holding shares as "beneficial owner" (or in "street name")?

Most stockholders are considered "beneficial owners" of their shares, that is, they hold their shares through a broker, bank, or other nominee rather than directly in their own name. As summarized below, there are some distinctions between shares held of record and those owned beneficially or in "street name."

Stockholder of record: If your shares are registered directly in your name with our transfer agent, you are considered the "stockholder of record" with respect to those shares and we are sending the proxy materials directly to you. As a stockholder of record, you have the right to vote by written proxy, Internet or telephone before the annual meeting or by Internet during the annual meeting.

Beneficial owner: If your shares are held in a stock brokerage account or by a bank or other nominee, you are considered the "beneficial owner" of shares held in street name, and these proxy materials are being forwarded to you by your broker, bank, or nominee (who is considered the stockholder of record with respect to those shares). As a beneficial owner, you have the right to direct your broker, bank, or nominee as to how to vote your shares if you follow the instructions you receive from your broker, bank, or nominee. You are also invited to attend the annual meeting. Instructions on how to participate in the annual meeting of stockholders will be included in the materials you receive from your broker, bank, or nominee and are also posted online at www.proxyvote.com.

What are the different methods that I can use to vote my shares of common stock?

By Internet before the annual meeting: Stockholders of record can vote their shares via the Internet at www.proxyvote.com 24 hours a day, seven days a week, until 11:59 p.m. Eastern Time on December 18, 2023, by using the 16-digit control number, which is on the proxy card or in the instructions accompanying the Notice of Internet Availability of Proxy Materials. Beneficial owners may vote by telephone or the Internet if their banks, brokers or nominees make those methods available, by following the instructions provided to them with the proxy materials.

By written proxy, telephone, or Internet before the annual meeting: Stockholders of record who received printed proxy materials can vote their shares by marking, signing, and timely returning the enclosed proxy card. Beneficial owners must follow the directions provided by their broker, bank, or other nominee in order to direct such broker, bank, or nominee as to how to vote their shares. Stockholders of record who received printed proxy materials can vote their shares by telephone at 1-800-690-6903until 11:59 p.m. Eastern Time on December 18, 2023 or via the Internet at www.proxyvote.com 24 hours a day, seven days a week, until 11:59 p.m. Eastern Time on December 18, 2023, in each case by using the 16-digitcontrol number, which is on the proxy card or in the instructions accompanying the proxy materials. Beneficial owners may also vote by telephone or the Internet before the annual meeting if their banks, brokers, or nominees make those methods available, by following the instructions provided to them with the proxy materials.

By Internet during the annual meeting: Stockholders of record may vote by Internet during the annual meeting at www.virtualshareholdermeeting.com/GWRE2023. Instructions on how to attend and vote during the annual meeting are described at www.proxyvote.com and stockholders will need their 16-digit control number which is on the proxy card or in the instructions accompanying the proxy materials in order to vote. Beneficial owners may not vote their shares at the annual meeting unless they request and obtain a valid proxy from the bank, broker or other nominee that holds their shares.

How many shares must be present to hold the annual meeting?

A majority of our outstanding shares as of the record date must be present at the annual meeting of stockholders in order to hold the annual meeting and conduct business. This is called a quorum.

Your shares will be counted for purposes of determining if there is a quorum, whether representing votes for, against, or abstained, or broker non-votes, if you:

• Are present and vote by Internet during the annual meeting; or
• Have voted on the Internet before the annual meeting, by telephone, or by properly submitting a proxy card or voting instruction form by mail.

If there are not enough shares present both by Internet and by timely and properly submitted proxies to constitute a quorum, the annual meeting may be adjourned until such time as a sufficient number of shares are present.

Guidewire Software, Inc.

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2023 Proxy Statement

How are abstentions counted?

Stockholders may choose to abstain or refrain from voting their shares on one or more issues presented for a vote at the annual meeting. However, for purposes of determining the presence of a quorum, abstentions are counted as present. For the purpose of determining whether the stockholders have approved a matter, abstentions will be treated as represented and entitled to vote and, therefore, will have the same effect on the outcome of a matter being voted on at the annual meeting as a vote "AGAINST," except in the election of directors, where abstentions will have no effect on the outcome.

What if a stockholder does not provide a proxy, or if a proxy is returned, it does not specify a choice for one or more issues?

Stockholders should specify their choice for each issue to be voted upon at the annual meeting. If no proxy is returned or if a proxy is signed and returned but no specific instructions are given on one or more of the issues to be voted upon at that annual meeting, proxies will be voted in accordance with applicable rules, laws, and regulations as follows:

Stockholders of Record. If you are a stockholder of record and you do not return a proxy or attend and vote at the annual meeting, your shares will not be voted at our annual meeting and your shares will not be counted for purposes of determining whether a quorum exists for the annual meeting. If you do return a signed proxy but you fail to specify how your shares should be voted on one or more issues to be voted upon at the annual meeting, then to the extent you did not specify a choice, your shares will be voted: (i) FOR Proposal One for the election of all of the director nominees; (ii) FOR Proposal Two ratifying the selection of KPMG LLP as our independent registered public accounting firm; (iii) FOR Proposal Three approving, on an advisory basis, the compensation of our named executive officers, as disclosed in this proxy statement; and (iv) FOR Proposal Four approving the amendment and restatement of the Guidewire Software, Inc. Amended and Restated 2020 Stock Plan.

Beneficial Owners. If you are a beneficial owner and (i) you do not provide your broker or other nominee who holds your shares with voting instructions, (ii) you do not request, obtain, and return a valid proxy from the organization that holds your shares giving you the right to vote the shares at our annual meeting, or (iii) you do provide a voting instruction card or a valid proxy card but you fail to specify your voting instructions on one or more of the issues to be voted upon at our annual meeting, under applicable rules, your broker or other nominee may exercise discretionary authority to vote your shares on routine proposals, but may not vote your shares on non-routine proposals.

The shares that cannot be voted by brokers and other nominees on non-routine matters, but are represented at the annual meeting, will be deemed present at our annual meeting for purposes of determining whether the necessary quorum exists to proceed with the annual meeting, but will not be considered entitled to vote on the non-routine proposals.

We believe that under applicable rules Proposal Two: Ratification of Appointment of Independent Registered Public Accounting Firm is considered a routine matter for which brokerage firms may vote shares that are held in the name of brokerage firms and which are not voted by the applicable beneficial owners.

However, we believe that Proposal One: Election of Directors, Proposal Three: Non-binding, advisory vote on compensation

of named executive officers and Proposal Four: Amendment and Restatement of the Guidewire Software, Inc. Amended and Restated 2020 Stock Plan are considered non-routinematters under applicable rules. Accordingly, brokers or other nominees cannot vote on these proposals without instructions from beneficial owners.

How do I change or revoke my proxy?

You may revoke your proxy and change your vote at any time before the final vote at the annual meeting. You may vote again on a later date on the Internet or by telephone (only your latest Internet or telephone proxy submitted prior to the annual meeting will be counted), or by signing and returning a new proxy card with a later date, or by attending the annual meeting and voting by Internet during the meeting. However, your attendance at the annual meeting will not automatically revoke your proxy unless you vote again at the annual meeting or specifically request in writing that your prior proxy be revoked.

What does it mean if I receive more than one proxy card?

It means that your shares are registered differently or you have multiple accounts. Please vote all of these shares separately to ensure all of the shares you hold are voted.

Guidewire Software, Inc.

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2023 Proxy Statement