DEF 14A of Guidewire Software, Inc., Nov 2, 2023

DEF 14A of Guidewire Software, Inc.

Filed Nov 2, 2023 · FY20230001528396-23-000123

Open on EDGAR

  1. Our Board of Directors

    Our Board of Directors

  2. Our Board of Directors

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

  3. Our Board of Directors

    | Chairperson | | Member | |

  4. Our Board of Directors

    | Guidewire Software, Inc. | ii | 2023 Proxy Statement |

  5. Our Board of Directors

    GUIDEWIRE SOFTWARE, INC.

  6. Director Nominees

    Director Nominees Our Board believes that directors who provide a significant breadth of experience, knowledge, and abilities in areas relevant to our business, while also representing a diversity of perspectives, contribute to a well-balanced and effective board. The following tables provide information concerning our Director Nominees as self-reported during our fiscal year 2023.

  7. Director Nominees

    | Average Director Age | | Average Director Tenure | | Board Diversity in Gender | | Board Diversity in Underrepresented Communities(11) | | | | 60 years | | 6.46 years | | 37.50% | | 25.00% | | | | Board Skill | Marcus S. Ryu | Paul Lavin | Mike Rosenbaum | David S. Bauer | Margaret Dillon | Michael C. Keller | Catherine P. Lego | Rajani Ramanathan | | Scaling a SaaS business(1) | X | | X | X | | | | X | | Modern cloud technologist(2) | | | X | X | | | | X | | Cybersecurity and infrastructure(3) | | | X | X | | X | | X | | Insurance industry(4) | X | X | X | | X | X | | | | Enterprise sales(5) | X | X | X | | | X | | | | Investment(6) | | | X | X | X | | X | X | | CEO experience(7) | X | X | X | | | | | | | Financial(8) | X | X | | | X | | X | | | People and compensation(9) | X | X | X | | X | X | X | X | | Governance, risk, and compliance(10) | X | X | X | X | X | X | X | X | | Years on Board | 22 | 10 | 4 | 1 | 4 | 4 | 4 | 2 | | Age | 50 | 61 | 52 | 63 | 64 | 63 | 67 | 56 | | Gender | M | M | M | M | F | M | F | F | | Self-identify as member of an underrepresented community(11) | Y | N | N | N | N | N | N | Y | | Veteran/Military Service(12) | N | N | Y | N | N | N | N | N |

  8. Director Nominees

    (1)Experience growing successful SaaS companies, including scale, margin expansion, and maturity. (2)Knowledge and experience in technology architecture, including SaaS, cloud-based platforms, integrated solutions, and customers’ data journey. (3)Insight in cybersecurity risk, technology infrastructure, business prioritization, and customer drivers. (4)Insight and experience in the P&C Insurance Industry globally. (5)Knowledge and experience managing sales and selling core enterprise software/SaaS offerings. (6)Experience creating long-term value through investment, acquisitions, and growth strategies. (7)Expertise shaping strategy, performance, prioritization, and scale leadership. (8)Experience in financial strategy, accounting, and reporting. (9)Expertise in aligning company customer, performance, rewards, and talent with strategy as well as remote and flexible work strategies. (10)Experience in public company corporate governance, privacy, compliance, policy, activism, and creating long-term sustainable value. (11)The term “underrepresented community,” as used herein, means Black, African American, Hispanic, Latinx, Asian, Pacific Islander, Native American, Native Hawaiian, Alaska Native, Two or More Races, or LGBTQ+. (12)The term “Veteran/Military Service” as used herein, means current full-time active duty with the U.S. Armed Forces, or any past service on active duty in the U.S. Armed Forces, Reserves, or National Guard.

  9. Director Nominees

    | Guidewire Software, Inc. | 8 | 2023 Proxy Statement |

  10. Director Nominees

    | Marcus S. Ryu Age: 50 Director Since: 2001 | Marcus S. Ryu is the Chairman of our Board, a position he has held since August 2019. Mr. Ryu has served as a Partner at Battery Ventures, a venture capital and private equity firm, since October 2022. From 2010 to August 2019, Mr. Ryu was Guidewire’s President and CEO and had overall responsibility for our operations and strategic direction. Since co-founding the Company in 2001, he held a variety of roles for the Company, including securing key customer relationships, communicating our value proposition, defining our product strategy, and has managed the engineering, sales, services, and strategy departments. He has served on our Board since 2001. Before Guidewire, Mr. Ryu was Vice President of Strategy at Ariba, Inc. and an Engagement Manager at McKinsey & Company. He currently serves as an advisor to multiple private technology companies and is a member of the board of directors of Checkr, Inc., a privately held company in the background check industry; BloomReach, Inc., a privately held company that offers a digital experience platform; Bestow, a privately held company that serves the life insurance industry; and Fairmatic, a privately held company that provides telematics-based commercial auto insurance. He has an A.B. from Princeton University and a B.Phil. from New College, Oxford University. | | | Our Board believes that Mr. Ryu is qualified to serve as a director based on his experience as co-founder and former CEO of Guidewire and his extensive service across a broad spectrum of Guidewire functions, including strategy, business development, operations, engineering, and marketing. |

  11. Director Nominees

    | Paul Lavin Age: 61 Director Since: 2014 | Paul Lavin is our Lead Independent Director and has served on our Board since 2014. Mr. Lavin is the President and Chief Executive Officer of American Health Holding, Inc. where he joined the company in 2008. Since 2017, he has served as Executive Director of First Health Network. Both are leading health insurance-related companies and subsidiaries of CVS/Aetna. Prior to joining CVS/Aetna, Mr. Lavin was a Managing Director at KPMG Consulting/Bearingpoint, where his focus was on financial services, primarily insurance. Mr. Lavin was formerly a Senior Vice President at Prudential, an executive at Alexander & Alexander, a Principal at Mercer Management Consulting, and an auditor at Price Waterhouse, where he was a CPA. He holds both a B.S. in Economics and an M.B.A. from the University of Pennsylvania's Wharton School of Business. | | | Our Board believes that Mr. Lavin is qualified to serve as a director based on his executive leadership roles and broad expertise in the industry, including as a systems integrator in the consulting and insurance industries. |

  12. Director Nominees

    | Guidewire Software, Inc. | 9 | 2023 Proxy Statement |

  13. Director Nominees

    | Mike Rosenbaum Age: 52 Director Since: 2019 | Mike Rosenbaum is our Chief Executive Officer (“CEO”) and has served on our Board since he became our CEO in August 2019. Prior to joining Guidewire, Mr. Rosenbaum was EVP Product at salesforce.com, inc. (“Salesforce”), with responsibility for vision, strategy, product management, customer success and adoption from January 2016 to July 2019. Since joining Salesforce in 2005, Mr. Rosenbaum held several leadership positions and drove many of Salesforce’s most notable product achievements. Prior to joining Salesforce, Mr. Rosenbaum held various technology and marketing roles at Siebel Systems from 2002 to 2005 and served in the U.S. Navy as a submarine officer from 1994 to 1999. Mr. Rosenbaum holds a B.S. in Systems Engineering from the United States Naval Academy and an M.B.A. from the Haas School of Business at the University of California Berkeley. | | | Our Board believes that Mr. Rosenbaum is qualified to serve as a director because of his experience in growing a cloud company and his leadership abilities, including his experience in leading product development and go-to-market strategy at Salesforce. |

  14. Director Nominees

    | David S. Bauer Age: 63 Director Since: 2022 | David S. Bauer has served on our Board since October 2022. Mr. Bauer currently serves as Managing Partner and Co-Founder at Holding Ground Decision Intelligence LLC, which provides strategic technology assessment and diligence services for investment companies, boards, and executives, a position he has held since January 2020. From November 2014 to January 2020, Mr. Bauer served as Managing Partner at Sand Hill East LLP, and provided early-stage companies with go-to-market, product, security, technology, and operations advisory services. He also previously served as Chief Technology Officer at Asurion, and as Chief Information Security Officer at Morgan Stanley and Merrill Lynch. Mr. Bauer holds a B.A. and M.S. in Computer Science from Rutgers University. | | | Our Board believes that Mr. Bauer is qualified to serve as a director based on his extensive and broad background in business management, including his experience in software development, information security expertise and information technology leadership, and his past service as chief information security officer at Morgan Stanley and Merrill Lynch. |

  15. Director Nominees

    | Guidewire Software, Inc. | 10 | 2023 Proxy Statement |

  16. Director Nominees

    | Margaret Dillon Age: 64 Director Since: 2019 | Margaret Dillon has served on our Board since September 2019. From December 1993 to September 2017, Ms. Dillon served in various roles at Liberty Mutual Insurance Company, a property and casualty insurer, including as Senior Vice President and Chief Financial Officer, Personal Insurance, and as Executive Vice President and Chief Customer Officer, U.S. Consumer Markets. Ms. Dillon also serves on the boards of Hi Marley, a privately held SaaS company providing an intelligent communication platform for the insurance industry since February 2022, and White Mountains Insurance Group, a publicly held diversified insurance and related financial services holding company since May 2021. Ms. Dillon holds both a B.S. in Computer Science and an M.S. in Finance from Boston College. | | | Our Board believes that Ms. Dillon is qualified to serve as a director based on her extensive and broad background in business management, including her experience as chief financial officer and chief customer officer of a Fortune 500 company, and her property and casualty insurance industry experience. |

  17. Director Nominees

    | Michael C. Keller Age: 63 Director Since: 2019 | Michael C. Keller has served on our Board since September 2019 and as our Lead Customer Advocate since March 2020. Mr. Keller also serves as a director of Encova Mutual Insurance Group since August 2020, and as Strategic Advisor to Earnix, a privately held company providing mission-critical composable and cloud-based intelligent solutions across pricing, rating, underwriting, product personalization and telematics, since January 2023. From June 2001 to June 2018, Mr. Keller served as the Executive Vice President and Chief Information Officer at Nationwide Insurance and Financial Services, a mutual insurance and financial services company. From January 1998 to May 2001, Mr. Keller served as Chief Technology Officer at JPMorgan Chase & Co. (Formerly Bank One), a commercial banking and financial services company. Mr. Keller holds the CERT Certificate in Cybersecurity Oversight by CMU Software Engineering Institute and the National Association of Corporate Directors. Mr. Keller is also Directorship Certified® by the National Association of Corporate Directors. Mr. Keller graduated with a B.S. in Mathematics from the University of Michigan. | | | Our Board believes that Mr. Keller is qualified to serve as a director based on his extensive and broad background in business management, including his experience as chief information officer and chief technology officer of Fortune 500 companies, and his property and casualty insurance industry experience. |

  18. Director Nominees

    | Guidewire Software, Inc. | 11 | 2023 Proxy Statement |

  19. Director Nominees

    | Catherine P. Lego Age: 67 Director Since: 2019 | Catherine P. Lego has served on our Board since September 2019. Ms. Lego also serves on the board of directors of Cirrus Logic, Inc., a publicly traded leader in low-power, high-precision mixed-signal processing solutions for mobile and consumer applications, where she is chair of the nominating and corporate governance committee since 2020 and joined its audit committee in July 2023. From 2009 to 2022, Ms. Lego was a member of the board of directors of Lam Research Corporation, a publicly traded wafer fabrication equipment company, where she was, at various times, the chair of the audit committee (2009-2014), a member of the audit committee (2020-2022), the chair of the compensation committee (2015-2020), and a member of its nominating and governance committee (2014-2022). From July 2016 to May 2021, she served on the board of directors of IPG Photonics Corporation, a publicly traded producer of high-power fiber lasers, where she served as the chair of its compensation committee and as a member of its audit committee. From 2013 to 2016, she was a member of the board of directors of Fairchild Semiconductor International Inc., a fabricator of power management devices, where she was a member of the compensation committee and nominating and governance committee. From 1989 to 2016, except from 2002-2004, she was a member of the board of directors of SanDisk Corporation, a publicly traded global developer of flash memory storage solutions, where she was the chair of the audit committee. Ms. Lego also served on the board of directors of Cypress Semiconductor Corporation from 2018 through its merger with Infineon Technologies in April 2020, where she was the chair of the audit committee and a member of the nominating and corporate governance committee. From June 1992 to December 2018, Ms. Lego was an angel investor and financial consultant to early stage technology companies via Lego Ventures, LLC, where she served as its principal and owner until December 2018. She previously practiced as a certified public accountant with Coopers & Lybrand (now PricewaterhouseCoopers). Ms. Lego holds a B.A. in Economics and Biology from Williams College and an M.S. in Accounting from the New York University Stern School of Business. | | | Our Board believes that Ms. Lego is qualified to serve as a director based on her extensive and broad background in business management and her service on the boards of several public companies in the technology sector. |

  20. Director Nominees

    | Guidewire Software, Inc. | 12 | 2023 Proxy Statement |

  21. Director Nominees

    | Rajani Ramanathan Age: 56 Director Since: 2021 | Rajani Ramanathan has served on our Board since June 2021. Ms. Ramanathan currently serves as an advisor and director to several public and private companies in the AI, VR, Blockchain and connected (IoT) technology space. Since October 2021, she has served on the board of Hayden AI, a privately held company that provides smart city solutions and developed the world’s first autonomous traffic management platform. Since July 2022, Ms.Ramanathan has served on the board of Faro Technologies, a publicly traded company serving 3D Metrology, AEC (Architecture, Engineering & Construction), O&M (Facilities Operations and Maintenance) and Public Safety Analytics markets. She serves on their Talent Development and Compensation Committee. Since May 2023, she has served on the board of Sportradar, a public company that is leading sports technology at the intersection of sports, media and betting. She serves on their Audit Committee. From June 2014 to present, Ms. Ramanathan has served as a member of the board of directors of ESI group, a French publicly traded company providing virtual prototyping software solutions and services. From July 2015 to July 2022, she chaired ESI’s Technology and Marketing Committee and since September 2022, she has chaired ESI’s Compensation Committee and their Nomination and Governance Committee. From June 2000 to March 2014, Ms. Ramanathan served in a variety of roles at Salesforce, a public cloud software company, and her last position with them was as Chief Operating Officer and Executive Vice President, Technology and Products. Ms. Ramanathan holds a B.A. in Psychology from University of Madras and a postgraduate diploma in Marketing and Sales Management from Rajendra Prasad Institute of Communication and Management. | | | Our Board believes that Ms. Ramanathan is qualified to serve as a director based on her extensive and broad background in cloud software operations and business management and her service on the boards of several public companies in the technology sector. |

  22. Director Nominees

    | Guidewire Software, Inc. | 13 | 2023 Proxy Statement |

  23. Director Nominees

    | | | Proposal Two | | | | Ratification of Appointment of Independent Registered Public Accounting Firm Recommendation On the recommendation of the audit committee of our Board (the “Audit Committee”), our Board has appointed KPMG LLP (“KPMG”), independent public accountants, to audit our financial statements for the fiscal year ending July 31, 2024. We are submitting this selection to our stockholders for ratification. Although we are not required to seek stockholder approval for this appointment, we believe it is sound corporate practice to do so. KPMG has served as our auditor since 2006. Representatives from KPMG will attend the annual meeting to respond to any appropriate questions and will have the opportunity to make a statement, if they so desire. If the stockholders do not ratify the appointment of KPMG, the Audit Committee will reconsider the appointment. In the vote on the ratification of the selection of KPMG as our independent registered public accounting firm, stockholders may: •Vote in favor of ratification; •Vote against ratification; or •Abstain from voting on ratification. | | | The Board recommends a vote "FOR" the ratification of KPMG as our independent registered public accounting firm for the fiscal year ending July 31, 2024. | |

  24. Director Nominees

    Assuming a quorum is present, the selection of KPMG as our independent registered public accounting firm will be ratified if the affirmative vote of a majority of the shares represented and entitled to vote on the matter at the annual meeting is obtained. In the event that the stockholders do not ratify the selection of KPMG, the appointment of the independent registered public accounting firm will be reconsidered by the Audit Committee.

  25. Information About the Board and Corporate Governance

    Information About the Board and Corporate Governance Our Board, which is elected by our stockholders, is responsible for directing and overseeing our business and affairs. In carrying out its responsibilities, the Board selects and monitors our top management, provides oversight of our financial reporting processes, and determines and implements our corporate governance policies. Our Board and management are committed to good corporate governance to ensure that we are managed for the long-term benefit of our stockholders, and we have a variety of policies and procedures to promote such goals. To that end, during the past year, our management reviewed our corporate governance policies and practices to ensure that they remain consistent with the requirements of the Sarbanes-Oxley Act of 2002 (the “Sarbanes-Oxley Act”), SEC rules, and the listing standards of the New York Stock Exchange (“NYSE”). Besides verifying the independence of the members of our Board and committees (which is discussed in the section titled “Independence of the Board” below), at the direction of our Board, we also: •Periodically review and make necessary changes to the charters for our audit, compensation, nominating and corporate governance, and risk committees; •Have established disclosure control policies and procedures in accordance with the requirements of the Sarbanes-Oxley Act and the rules and regulations of the SEC; •Have a procedure for receipt and treatment of anonymous and confidential complaints or concerns regarding audit or accounting matters; and •Have a code of business conduct and ethics that applies to our officers, directors, and employees. In addition, we have adopted a set of corporate governance guidelines. The NCG Committee is responsible for reviewing our corporate governance guidelines from time to time and reporting and making recommendations to the Board concerning corporate governance matters. Our corporate governance guidelines address such matters as: •Director Independence – Independent directors must constitute at least a majority of our Board; •Monitoring Board Effectiveness – Our Board must conduct an annual self-evaluation of the Board and its committees; •Chairman of the Board – The roles and responsibilities of the Chairman of the Board are generally described in our corporate governance guidelines, as described under the section titled, “Chairman of the Board” below; •Lead Independent Director – The roles and responsibilities of the Lead Independent Director are generally described in our corporate governance guidelines, as described under the section titled, “Lead Independent Director” below; •Executive Sessions of Directors – The Chairman of the Board regularly leads meetings among non-employee directors without management present and the Lead Independent Director regularly leads meetings among the independent directors; •Board Access to Independent Advisors – Our Board as a whole, and each of its committees separately, have authority to retain independent consultants, counselors, or advisors as each deems necessary or appropriate; •Board Committees – All members of the audit, compensation, nominating and corporate governance and risk committees are independent in compliance with applicable NYSE criteria; and •External Programs – We make director education program information available to our Board regularly, encourage them to attend director education programs, and reimburse the costs of attending such programs. Copies of our corporate governance guidelines, code of business conduct and ethics, and committee charters can be found on our website at www.guidewire.com under “About/Investor Relations/Corporate Governance.”

  26. Information About the Board and Corporate Governance

    | Guidewire Software, Inc. | 25 | 2023 Proxy Statement |

  27. Consideration of Director Nominees

    Consideration of Director Nominees Stockholder Nominees. Our amended and restated bylaws permit stockholders to nominate directors for consideration at our annual stockholder meeting. For a description of this process, see the section titled “Questions and Answers About the Annual Meeting, the Proxy Materials and Voting Your Shares - How can stockholders submit a proposal for inclusion in our proxy statement for the 2024 annual meeting?” above. If any materials are provided by a stockholder in connection with the nomination of a director candidate, such materials are forwarded to the NCG Committee. The NCG Committee's policy is to consider properly submitted stockholder nominations. In evaluating all director nominations, the NCG Committee seeks to balance an individual's knowledge, experience and capabilities and compliance with the membership criteria set forth below under the section titled “Director Qualifications.” Director Qualifications. Our corporate governance guidelines apply membership criteria to nominees recommended by the NCG Committee for a position on our Board. These include judgment, diversity, skills, background, and experience in light of our Board’s present composition and the current challenges and needs of our Board and its committees. The NCG Committee also takes into account the independence, financial literacy, and financial expertise standards required under our corporate

  28. Consideration of Director Nominees

    | Guidewire Software, Inc. | 31 | 2023 Proxy Statement |

  29. Consideration of Director Nominees

    governance guidelines and committees' charters and applicable laws and regulations, and the ability of the candidate, in light of the candidate's present activities and our corporate governance guidelines, to devote the necessary time and attention to serving as a director and a committee member. Each director must represent the interests of all stockholders. While we take into account diversity of background, experience, knowledge, and abilities and are committed to diversity, we do not have a formal policy that requires nominees to meet specific criteria. Identifying and Evaluating Nominees for Directors. The NCG Committee utilizes a variety of methods to identify and evaluate director nominees. The NCG Committee plans to assess the appropriate size of our Board from time to time and whether any vacancies are expected. In the event that vacancies are anticipated or otherwise arise, the NCG Committee decides whether to fill such vacancies and, if so, considers various potential candidates. Candidates may come to the attention of the NCG Committee through current Board members, professional search firms engaged by the NCG Committee, stockholders, or others. These candidates may be evaluated at meetings of the NCG Committee and may be considered at any point during the year.

  30. Information Regarding Compensation of Directors and Executive Officers

    Information Regarding Compensation of Directors and Executive Officers

  31. Director Compensation

    Director Compensation We believe that a combination of cash and equity compensation is appropriate to attract and retain the individuals we desire to serve on our Board and that this approach is comparable to the policies of our peers. More specifically, our cash compensation policies are designed to encourage frequent and active interaction between our directors and our executives, both during and between formal meetings, as well as to compensate our directors for their time and effort. Further, we believe that it is important to align the long-term interests of our non-employee directors with those of the Company and its stockholders and that awarding equity compensation to, and thereby increasing ownership of our common stock by, our non-employee directors is an appropriate means to achieve this alignment. The Compensation Committee reviews non-employee director compensation approximately every year, to determine the appropriate compensation for service on the Board. The Compensation Committee last reviewed non-employee director compensation in December 2022. In doing so, the Compensation Committee reviewed and considered a peer group study prepared by its then-retained executive compensation advisor, Aon Human Capital Solutions, a division of Aon plc (“Aon”). The Compensation Committee did not strictly target any specific levels of pay, and instead, used the comparative market data provided by Aon as an important reference point in its decision-making process. Based on its review, for calendar year 2023, the Compensation Committee recommended, and our Board agreed, to not make any changes to our non-employee director cash compensation from calendar year 2022, other than to increase the value of the initial and annual RSU grants to $225,000 from $200,000. Our non-employee directors receive an annual cash retainer for Board service in addition to equity compensation, as set forth in further detail in the table below. Our non-employee directors do not receive fringe or other benefits. Directors who are also one of our employees are not entitled to additional compensation for serving as a director.

  32. Director Compensation

    | Position | | Annual Cash Retainer ($)(1) | Equity Compensation ($)(2) | | Board Membership | | 50,000 | Initial grant of restricted stock units ("RSUs") with a value of $225,000 (pro-rated) and annual grant of RSUs with a value of $225,000 | | Position | | Additional Annual Cash Retainer ($) | Additional Equity Compensation ($) | | Chairman of the Board | | 50,000 | — | | Lead Independent Director | | 50,000 | — | | Lead Customer Advocate | | 30,000 | — | | Audit Committee | Chair | 25,000 | — | | | Non-Chair Member | 12,500 | — | | Compensation Committee | Chair | 20,000 | — | | | Non-Chair Member | 10,000 | — | | Nominating and Corporate Governance Committee | Chair | 10,000 | — | | | Non-Chair Member | 5,000 | — | | Risk Committee | Chair | 20,000 | — | | | Non-Chair Member | 10,000 | — |

  33. Director Compensation

    (1)The annual cash retainers are payable in quarterly installments and pro-rated based on number of days served. (2)The RSU grants vest on the one-year anniversary of the grant date. However, if the non-employee director's service ends at the next annual meeting of stockholders and such meeting occurs before the one-year anniversary of the grant date, the RSU shall be fully vested on the date of such annual meeting. All RSU grants held by non-employee directors will fully vest upon a sale of the Company.

  34. Director Compensation

    | Guidewire Software, Inc. | 37 | 2023 Proxy Statement |

  35. Director Compensation

    The table below shows the compensation received or earned by each of our non-employee directors during fiscal year 2023. Of our directors during fiscal year 2023, Mike Rosenbaum was an employee and did not receive any additional compensation for his service as our director during this time. Mr. Rosenbaum was a named executive officer for fiscal year 2023 and information regarding his compensation for the year is presented below in the “Summary Compensation Table.”

  36. DIRECTOR COMPENSATION TABLE

    DIRECTOR COMPENSATION TABLE

  37. DIRECTOR COMPENSATION TABLE

    | Name | Fees Earned or Paid in Cash ($) | Stock Awards ($)(1) | Total ($) | | Marcus Ryu(2) | 99,725 | 225,841 | 325,566 | | Paul Lavin(3) | 117,177 | 225,841 | 343,018 | | David Bauer(4) | 58,269 | 267,469 | 325,738 | | Andrew Brown(5) | 28,594 | — | 28,594 | | Margaret Dillon(6) | 72,301 | 225,841 | 298,142 | | Michael C. Keller(7) | 109,698 | 225,841 | 335,539 | | Catherine P. Lego(8) | 79,780 | 225,841 | 305,621 | | Rajani Ramanathan(9) | 78,132 | 225,841 | 303,973 |

  38. DIRECTOR COMPENSATION TABLE

    (1)The amounts shown reflect the aggregate grant date fair value of RSUs granted during fiscal year 2023, determined in accordance with Financial Accounting Standards Board (“FASB”) Accounting Standards Codification (“ASC”) Compensation--Stock Compensation (“Topic 718”). These amounts do not represent the actual amounts paid to or realized by the non-employee directors during fiscal year 2023. Pursuant to SEC rules, these amounts exclude the impact of estimated forfeitures related to service-based vesting conditions. See Note 10 of the consolidated financial statements in the 2023 Annual Report on Form 10-K regarding assumptions underlying valuation of equity awards. (2)As of July 31, 2023, Mr. Ryu held 3,736 unvested RSUs. (3)As of July 31, 2023, Mr. Lavin held 3,736 unvested RSUs. (4)As of July 31, 2023, Mr. Bauer held 3,736 unvested RSUs. David Bauer was appointed as a member of our Board effective October 1, 2022. Upon appointment, Mr. Bauer received a pro-rated initial grant of RSUs and was entitled to cash compensation for his services as described under “Director Compensation” above. (5)Mr. Brown’s service on our Board expired at last year’s annual meeting of stockholders, which was held on December 20, 2022. As of July 31, 2023, Mr. Brown held no outstanding, unvested equity awards. (6)As of July 31, 2023, Ms. Dillon held 3,736 unvested RSUs. (7)As of July 31, 2023, Mr. Keller held 3,736 unvested RSUs. (8)As of July 31, 2023, Ms. Lego held 3,736 unvested RSUs. (9)As of July 31, 2023, Ms. Ramanathan held 3,736 unvested RSUs.

  39. DIRECTOR COMPENSATION TABLE

    | Guidewire Software, Inc. | 38 | 2023 Proxy Statement |

  40. Compensation Program Design

    Compensation Program Design For fiscal year 2023, the compensation of our executive officers, including the NEOs, has consisted of base salary, a cash bonus opportunity, and equity compensation in the form of RSUs subject to performance-based vesting conditions tied to corporate financial and operational metrics (“Performance-Vesting RSUs”) and RSUs subject to time-based vesting conditions (“Time-Vesting RSUs”). Of these components, only base salary is fixed while the other components are variable based on the performance of both the Company and the individual executive officer, measured against specific objectives that are determined in advance. The key component of our executive compensation program has been equity awards in the form of Performance-Vesting RSUs and Time-Vesting RSUs. We use equity-based awards as we deem appropriate to offer our employees, including our executive officers, long-term equity incentives that align their interests with the long-term interests of our stockholders. We also have offered cash compensation in the form of base salaries, to reward individual contributions and compensate our executive officers for their day-to-day responsibilities, and annual cash bonuses, to drive and incentivize our executive officers to achieve our short-term strategic and operational objectives. In addition to these elements of our executive compensation program, we also provide executive officers, including our NEOs, with certain other indirect benefits, including participation in certain post-employment compensation arrangements. For a description of these other features of our compensation program, please refer to the section below titled “Executive Compensation Program Elements-Welfare and Other Benefits” and “Executive Agreements and Termination of Employment Arrangements.” We evaluate our philosophy and compensation programs as circumstances require, and at a minimum, we review executive compensation annually. As part of this review process, we apply our values and the objectives outlined above, while also considering whether our proposed compensation ensures that we remain competitive for talent, that we meet our retention objectives, and that our cost of replacement for a key employee is reasonable.

  41. Compensation-Setting Process

    While our CEO attends certain meetings of the Compensation Committee, the Compensation Committee meets outside the presence of our CEO when discussing his compensation and when discussing certain other matters. Decisions with respect to our CEO’s compensation are made by the Compensation Committee and our Board. The Compensation Committee also works with our CFO, our Chief People Officer, and our Chief Administrative Officer and General Counsel in evaluating the financial, accounting, tax, and retention implications of our executive compensation plans and arrangements. Role of Compensation Consultant The Compensation Committee is authorized to retain the services of one or more executive compensation advisors, as it sees fit, in connection with the oversight of our executive compensation program. For fiscal year 2023, the Compensation Committee engaged Aon from August 1, 2022 until June 30, 2023, as well as Semler Brossy Consulting Group, LLC (“Semler Brossy”) since May 18, 2023, to provide information, recommendations, and other advice relating to executive compensation. During fiscal year 2023, Aon performed the following projects for the Compensation Committee: •reviewed our general compensation principles for fiscal year 2023; •prepared an assessment of non-employee director compensation; •prepared an assessment of our executive officers’ total compensation, as well as each individual compensation component, including an analysis of cash compensation, equity compensation, and total direct compensation as compared to a composition of our peer group (described below); •prepared an analysis of competitive market compensation practices for certain executive positions; •assisted with the design of the overall equity program, including helping set grant levels for the Company as a whole; •analyzed pay survey data; •provided advice regarding best practices and compensation trends, including proxy advisory firms’ evolving positions on executive pay; and •performed a risk analysis of our compensation arrangements. During fiscal year 2023, Semler Brossy performed the following projects for the Compensation Committee: •oversaw the design and operation of our executive compensation program; •reviewed our executive compensation program and philosophy and advised on changes in light of evolving best practices; •assisted the Compensation Committee in the review, design, and improvement of short- and long-term incentive programs for our senior management team and other levels of management; and •worked with the Compensation Committee and risk management personnel in conducting pay-risk assessments and identifying areas for change and improvement. Aon and Semler Brossy both served at the discretion of the Compensation Committee. The Compensation Committee assessed the independence of Aon and Semler Brossy pursuant to applicable SEC and NYSE rules and concluded that no conflict of interest exists that would prevent Aon or Semler Brossy from independently advising the Company. Comparative Market Data To assist the Compensation Committee during its annual review of the competitiveness of compensation levels and the appropriate mix of compensation elements to our executive officers, including our NEOs, Aon prepared comparative market data on compensation practices and programs as well as guidance on industry best practices. The Compensation Committee, with guidance from Aon and input from senior management, determines the composition of our peer group and reevaluates this group on an annual basis. The Compensation Committee determined that our peer group for determining the compensation of our NEOs in fiscal year 2023 in connection with our annual compensation review would consist of 17 public software companies in the San Francisco Bay Area and other technology "hubs" with revenue between $400 million and $2 billion, including high revenue growth companies, and market capitalization between $4 billion and $40 billion. Below is a list of the companies in our peer group for setting fiscal year 2023 compensation for our NEOs:

  42. Compensation-Setting Process

    The evaluation of the peer group generally occurs in March of each year. In March 2023, our Compensation Committee reassessed our peer group for use in setting our fiscal year 2024 executive compensation, and determined to base it on publicly traded software companies in the San Francisco Bay Area and other technology “hubs” with revenue between $450 million and $2.5 billion, including high revenue growth companies, and market capitalization between $2 billion and $20 billion. Our Compensation Committee removed two companies from the fiscal year 2023 peer group listed above (Anaplan and Zendesk, Inc.) and added two new companies (BlackLine and Qualys) to the peer group so that the group contained a sufficient number of companies. Consideration of Say-On-Pay Advisory Vote At our December 20, 2022 annual meeting, we held a non-binding, advisory vote on the compensation of our NEOs (a “Say-on-Pay” vote), which received the support of approximately 91% of the votes cast. Our Board and Compensation Committee are encouraged by this level of stockholder support of our executive compensation program, and generally view this as an endorsement of our philosophy and how we have structured our compensation program. Given this level of stockholder support, the Compensation Committee concluded that our executive officer compensation program continues to align executive officer pay with stockholder interests and provides competitive pay that encourages retention and effectively incentivizes performance of talented executive officers. Accordingly, the Compensation Committee determined not to make any significant changes to our executive compensation program as a result of the Say-on-Pay vote. In addition, consistent with the recommendation of our Board and the preference of our stockholders as reflected in the non-binding, advisory vote on the frequency of future Say-on-Pay votes held at our December 15, 2020 annual meeting, we intend to continue holding an annual Say-on-Pay vote. We are committed to continuing our ongoing engagement with our stockholders on matters of executive compensation and corporate governance. As a result, we have continued to engage in a robust stockholder outreach program. In 2023, we reached out to our 25 largest institutional stockholders and key investors, with aggregate holdings of approximately 72% of our outstanding shares (as of June 30, 2023), to discuss our executive compensation and corporate governance programs and practices, and to solicit feedback and ensure that our Board and management have insight into the issues that are most important to our stockholders so that we can better understand our stockholders’ perspectives. While not all stockholders have accepted our invitation to engage as of November 2, 2023, we have held these calls with all invited stockholders who indicated an interest in participating in our annual stockholder outreach program. Our calls with stockholders were initiated by our Chief Administrative Officer and General Counsel and our Vice President of Investor Relations, and included the Chairs of our Compensation Committee and NCG Committee. During these discussions, and among many viewpoints shared, our stockholders expressed certain concerns as set forth in the following table. In connection with the Compensation Committee’s regular annual review process, our Board, the Compensation Committee, and the NCG Committee determined to take certain actions to address these concerns of our stockholders. The actions specifically taken by our Board, the Compensation Committee, and the NCG Committee included the following:

  43. Compensation-Setting Process

    | What We Heard During Our 2023 Outreach | What We Did in Response | | Closer alignment between the Company’s performance and certain equity awards granted to the management team | For fiscal year 2024, the Compensation Committee has approved changes to our Performance-Vesting RSUs program. The changes involve shifting to a three-year average performance measurement approach based on annual measurements of ARR and non-GAAP operating income which includes stock-based compensation expense. The annual FY24 performance-based RSUs will cliff vest at the end of the three-year performance period. The Compensation Committee has implemented an additional additive performance-based RSU modifier for our CEO and CRO which is based on the achievement of two conditions (i) at or above target performance for the FY24 performance-based RSUs, and (ii) significant stock-price milestones. The modifier increases the upside leverage of the annual performance-based RSU program to 250%. We believe that these changes will promote longer-term retention for our management team and incentivize long-term value creation for the Company. | | Stockholder dilution due to the Company’s practice of granting equity awards | On September 22, 2022, our Board approved a share repurchase program pursuant to which we may purchase up to $400 million of our outstanding shares of common stock. During the twelve months ended July 31, 2023, we repurchased a total of 4,041,284 shares at an average price of $64.78 per share. As of July 31, 2023, $138.2 million remained available for future share repurchases. In addition, beginning in fiscal year 2023, we implemented an equity choice program (entitled the MyChoice LTI Plan), whereby employees in professional or managerial roles (excluding senior executives such as our NEOs) who started prior to May 1, 2022 can choose to receive their annual refresh award entirely in the form of cash, entirely in form of RSUs, or in a mix of both (i.e., 50% in the form of RSUs and 50% in the form of cash). Whether an employee chooses RSUs, cash, or a mix of both, the award will generally vest quarterly over four years, subject to continued employment through each applicable vesting date. In order to receive RSUs, awards must be greater than $10,000. As a consequence, for employees choosing a 50% RSU/50% cash split, the relevant award must have a value of $20,000 or greater. For fiscal years 2023 and 2024, cash elections under the MyChoice LTI Plan effectively reduced dilution by approximately 430,000 shares of our common stock. | | Continue ESG and DEIB efforts | We continue to reinforce our commitment to ESG and DEIB matters in part by including certain ESG metrics as performance goals in our Bonus Plan in both fiscal year 2022 and 2023. In addition, we have engaged in various ESG and DEIB initiatives and have tasked certain Board committees to oversee such areas, as described above in this proxy statement under “Corporate Sustainability and Environmental, Social and Governance Matters.” We have also published our second annual ESG report, which is not incorporated herein by reference. We expect to continue our disclosure on ESG and DEIB efforts on an ongoing basis in response to supportive stockholder feedback. |

  44. Executive Compensation Program Elements

    Thereafter, the Compensation Committee reviews and recommends adjustments, as necessary or appropriate, to the base salaries of our executive officers on an annual basis. In doing so, the Compensation Committee exercises its judgment and discretion and considers several factors, including our overall financial and operational results for the prior fiscal year, the performance of the individual executive officer, the executive officer’s potential to contribute to our long-term strategic goals, her or his role and scope of responsibilities within our Company, her or his individual experience and skills, the executive officer’s compensation as compared to similarly situated executives at comparable companies in our peer group, and the input of our CEO. No specific formula is applied to determine the weight of each criterion. In September 2022, the Compensation Committee reviewed the base salaries of certain of our executive officers and management team, including the NEOs, and determined not to adjust the base salaries for our NEOs in view of our performance during fiscal year 2022. Further, the Compensation Committee took into account our peer group’s base salaries for similarly situated executives as an additional factor in determining base salaries for our NEOs. Accordingly, the Compensation Committee approved the annual base salaries for fiscal year 2023 as follows:

  45. Executive Compensation Program Elements

    * All fiscal year 2023 base salaries first became effective on November 1, 2022. Senior Executive Incentive Bonus Plan Our Senior Executive Incentive Bonus Plan (the “Bonus Plan”) applies to certain key executives, including all the NEOs, as selected by the Compensation Committee. The Bonus Plan provides for bonus payments based upon the attainment of performance targets established by the Compensation Committee related to financial and operational metrics with respect to the Company and its subsidiaries (the “Performance Goals”). Any bonuses paid under the Bonus Plan are based upon objectively determinable bonus formulas that tie such bonuses to one or more performance targets relating to the Performance Goals. The bonus formulas are adopted in each annual performance period by the Compensation Committee and communicated to each executive officer. No bonuses shall be paid under the Bonus Plan unless and until the Compensation Committee makes a determination with respect to the attainment of the performance objectives. Notwithstanding the foregoing, we can adjust or pay bonuses under the Bonus Plan based on achievement of individual performance goals or pay bonuses (including, without limitation, discretionary bonuses) to executive officers under the Bonus Plan based upon such other terms and conditions as the Compensation Committee may in its discretion determine. Each executive officer participating in the Bonus Plan has a targeted bonus opportunity set for each performance period. The Performance Goals will be measured at the end of each performance period after our financial reports have been published or such other appropriate time as the Compensation Committee determines. If the Performance Goals are met, payments will be made as soon as practicable following the end of each performance period. Subject to the rights contained in any agreement between the executive officer and the Company, an executive officer must be employed by the Company on the bonus payment date in order to be eligible to receive a bonus payment. Target Bonus Opportunities In September 2022, the Compensation Committee reviewed the target bonus opportunities of our executive officers and management team, including the applicable NEOs, and adjusted target bonus opportunities for each of our NEOs in view of their performance during fiscal year 2022 and considered several factors, including our peer group’s short-term incentive bonus target opportunity for similarly situated executives, our Company’s overall financial and operational results for the prior fiscal year, the performance of the individual executive officer, the executive officer’s potential to contribute to our long-term strategic goals, his or her role and scope of responsibilities within our Company, his or her individual experience and skills, the Compensation Committee’s sense of competitive market practices for annual bonuses and the recommendations of our CEO (for NEOs other than himself).

  46. Executive Compensation Program Elements

    | Named Executive Officer | Fiscal Year 2022 Target Bonus Opportunity (% of Base Salary) | Fiscal Year 2023 Target Bonus Opportunity (% of Base Salary) | | Mike Rosenbaum | 100 | 100 | | Jeff Cooper | 75 | 75 | | Priscilla Hung | 75 | 75 | | John Mullen | 100 | 100 | | Winston King | 75 | 75 |

  47. Target Cash Bonus Opportunity X Company Performance Factor

    Target Cash Bonus Opportunity X Company Performance Factor Company Performance Factor In fiscal year 2023, the bonuses of our executive officers, including the NEOs, who participated in our Bonus Plan were based on the performance of our Company during fiscal year 2023 as measured against the following pre-established corporate financial and operational metrics, which the Board deemed to be critical to enhancing stockholder value: •Annual Recurring Revenue (ARR) on a constant currency basis (the goal of this metric is to maximize annual recurring revenue); •Adjusted Non-GAAP Operating Profit (the goal of this metric is to achieve or exceed our profitability targets); and •Net Promoter Score (NPS)/Environmental, Social and Governance (ESG) Performance (the goal of this metric is to enhance efforts to achieve NPS and ESG goals). The Adjusted Non-GAAP Operating Profit metric is a non-GAAP financial measure. Specifically, the Adjusted Non-GAAP Operating Profit is derived from GAAP income (loss) from operations and excludes stock-based compensation expense, amortization of acquired intangibles, acquisition consideration holdback, net impact of assignment of lease agreement, and corporate bonus accrual exceeding 100%. See Appendix A to this proxy statement for further details regarding the Adjusted Non-GAAP Operating Profit metric and the reconciliation of the metric to GAAP income (loss) from operations as reported for purposes of GAAP from the Company’s audited financial statements. For fiscal year 2023, we used the Adjusted Non-GAAP Operating Profit metric as one of our corporate goals for the Bonus Plan instead of Adjusted Non-GAAP Expenses due to the determination of the Compensation Committee that the Adjusted Non-GAAP Operating Profit metric was more appropriate for measuring profitability and aligning executive officer compensation with the Company’s performance.

  48. Target Cash Bonus Opportunity X Company Performance Factor

    | Guidewire Software, Inc. | 47 | 2023 Proxy Statement |

  49. Target Cash Bonus Opportunity X Company Performance Factor

    The threshold, target, and maximum performance goals for each of these metrics were as follows in fiscal year 2023:

  50. Target Cash Bonus Opportunity X Company Performance Factor

    | Metric(1) | Weighting | Payout % Range (Threshold/Maximum) | Threshold | Target (100%) | Maximum | Actual Performance | | ARR(2) | 70% | 50% / 150% | $722M | $760M | $798M | $761M | | Adjusted Non-GAAP Operating Profit | 25% | 0% / 200% | ($39M) | ($19M) - ($9) | $1 | $19M | | NPS/ESG Performance(3) | 5% | 50% / 150% | —% | 5% | 10% | 4% |

  51. Target Cash Bonus Opportunity X Company Performance Factor

    (1)Achievement (other than for NPS/ESG performance) was calculated on a straight-line basis from (i) the threshold to the target and (ii) from the target to the maximum. Achievement at the target was credited at 100%. Achievement below threshold at either 50% (in the case of ARR and NPS/ESG Performance) or 0% (in the case of Adjusted Non-GAAP Operating Profit) results in 0% payout for the relevant metric under assessment. Further, payout is capped at 150% (in the case of ARR and NPS/ESG Performance) or 200% (in the case of Adjusted Non-GAAP Operating Profit); however, payout above 150% (in the case of ARR and NPS/ESG Performance) or 200% (in the case of Adjusted Non-GAAP Operating Profit) is at the discretion of our Board. (2)ARR is calculated on a constant currency basis per exchange rates at July 31, 2022. (3)The payout range for the threshold and maximum was 0% – 10%, with target at 5%. These metrics were determined in the first quarter of fiscal year 2023. Fiscal Year 2023 Bonus Decisions After the conclusion of fiscal year 2023, the Compensation Committee evaluated our financial and operational performance for the fiscal year and determined that a Company Performance Factor of 126% was appropriate. Based on this determination, the Compensation Committee approved cash bonuses for the applicable NEOs as follows:

  52. Target Cash Bonus Opportunity X Company Performance Factor

    | Named Executive Officer | Fiscal Year 2023 Target Bonus Opportunity (% of Base Salary) | Company Performance Factor (%) | Cash Bonus ($) | | Mike Rosenbaum | 100 | 126% | 943,500 | | Jeff Cooper | 75 | 126% | 377,400 | | Priscilla Hung | 75 | 126% | 400,988 | | John Mullen | 100 | 126% | 629,000 | | Winston King | 75 | 126% | 367,965 |

  53. Target Cash Bonus Opportunity X Company Performance Factor

    These bonuses to the NEOs for fiscal year 2023 were paid in fiscal year 2024, in accordance with normal Company practice.

  54. Equity Compensation

    Equity Compensation We use equity awards to incentivize and reward our executive officers, including the NEOs, for long-term corporate performance based on the value of our common stock and, thereby, to align their interests with those of our stockholders. Since fiscal year 2021, in consultation with Aon, we provide for only Performance-Vesting RSUs and Time-Vesting RSUs, with Performance-Vesting RSUs focusing mainly on ARR, as we determined that ARR was a key metric for the Company to align and drive performance in light of our cloud transition. We believed that for fiscal year 2023, Performance-Vesting RSUs and Time-Vesting RSUs provided a strong retention incentive for our executive officers, provided a moderate reward for growth in the market price of our common stock, and were less dilutive than stock options to our stockholders. Our equity award vehicles provide a strong incentive for our executive officers to remain employed with the Company as they require continued employment through the vesting period. Time-Vesting RSUs Time-Vesting RSUs generally vest quarterly over four years (except that for new hires, 25% of their Time-Vesting RSUs cliff vest on the first anniversary of the vesting commencement date, with the remaining portion vesting in equal quarterly installments over the three years thereafter), subject to an equity award holder’s continued employment through each applicable vesting date.

  55. Equity Compensation

    | Guidewire Software, Inc. | 48 | 2023 Proxy Statement |

  56. Equity Compensation

    Performance-Vesting RSUs 50% of the Performance-Vesting RSUs vest based on the satisfaction of both a three-year time condition and a one-year performance condition (the "First Tranche Performance-Vesting RSUs"). Assuming the applicable performance conditions are met, the First Tranche Performance-Vesting RSUs vest over three years with 33 1/3% of the earned amount cliff vesting on the first anniversary of the vesting commencement date, with the remaining portion vesting in equal annual installments over the two years thereafter. For the First Tranche Performance-Vesting RSUs, the performance condition for fiscal year 2023 (the “FY 23 Performance Condition”) was tied to the achievement of fiscal year 2023 ARR, measured on a constant currency basis using July 31, 2022 exchange rates. For the ARR target: (i) at the threshold ARR amount, the number of First Tranche Performance-Vesting RSUs eligible to vest would equal the target number of First Tranche Performance-Vesting RSUs (i.e., 50% of the target number of Performance-Vesting RSUs) multiplied by 50%; (ii) at the target ARR amount, the number of First Tranche Performance-Vesting RSUs eligible to vest would equal the target number of First Tranche Performance-Vesting RSUs multiplied by 100%; and (iii) at or above the maximum ARR amount, the number of First Tranche Performance-Vesting RSUs eligible to vest would equal the target number of First Tranche Performance-Vesting RSUs multiplied by 150%. If the ARR threshold is not attained, then none of the First Tranche Performance-Vesting RSUs would be eligible to vest. In addition, if our ARR amount exceeds the maximum ARR amount, then the number of First Tranche Performance-Vesting RSUs earned would still be capped at 150% of target. For fiscal year 2023, the Company was determined to have achieved an ARR amount in excess of the target amount, which resulted in 101.8% of the target number of First Tranche Performance-Vesting RSUs vesting in relation to FY 23 Performance Condition achievement. 33 1/3% of these earned First Tranche Performance-Vesting RSUs vested on the first anniversary of the vesting commencement date and the remainder will time-vest in equal annual installments over the next two years subject to the holder’s continued employment with us. The applicable goals for the FY 23 Performance Condition for the First Tranche Performance-Vesting RSUs were:

  57. Equity Compensation

    | | Threshold (50%) ($) | Target (100%) ($) | Maximum (150%) ($) | Actual Performance ($) | | ARR* | $722M | $760M | $798M | $761M |

  58. Equity Compensation

    *ARR is calculated on a constant currency basis per exchange rates at July 31, 2022. The remaining 50% of the Performance-Vesting RSUs vest based on the satisfaction of both a three-year time condition and a three-year performance condition (the “Second Tranche Performance-Vesting RSUs”). Assuming the applicable performance conditions are met, the Second Tranche Performance-Vesting RSUs will cliff vest at such time, subject to the holder’s continued employment with us. For the Second Tranche Performance-Vesting RSUs, the performance condition (the “FY 25 Performance Condition”) was tied to the achievement of FY 25 ARR, measured on a constant currency basis using July 31, 2022 exchange rates. For the ARR target: (i) at the threshold ARR amount, the number of Second Tranche Performance-Vesting RSUs eligible to vest would equal the target number of Second Tranche Performance-Vesting RSUs (i.e., 50% of the target number of Performance-Vesting RSUs) multiplied by 50%; (ii) at the target ARR amount, the number of Second Tranche Performance-Vesting RSUs eligible to vest would equal the target number of Second Tranche Performance-Vesting RSUs multiplied by 100%; and (iii) at or above the maximum ARR amount, the number of Second Tranche Performance-Vesting RSUs eligible to vest would equal the target number of Second Tranche Performance-Vesting RSUs multiplied by 150%. If the ARR threshold is not attained, then none of the Second Tranche Performance-Vesting RSUs would vest. In addition, if our ARR amount exceeds the applicable maximum ARR amount, then the number of Second Tranche Performance-Vesting RSUs that could vest would still be capped at 150% of target. The applicable goals for the FY 25 Performance Condition for the Second Tranche Performance-Vesting RSUs are:

  59. Equity Compensation

    | | Threshold (50%) ($) | Target (100%) ($) | Maximum (150%) ($) | Actual Performance ($) | | ARR | $900M | $1,000M | $1,100M | * |

  60. Equity Compensation

    *TBD, measured at July 31, 2025, our fiscal year 2025 fiscal year end, on a constant currency basis per exchange rates at July 31, 2022. The Compensation Committee may in its discretion adjust ARR targets for any inorganic ARR growth or loss due to mergers, acquisitions, or divestitures. In fiscal year 2021, we made a similar grant of Performance-Vesting RSUs as in fiscal year 2023 ("FY 21 Performance-Vesting RSUs”). 50% of the FY 21 Performance-Vesting RSUs vest based on the satisfaction of both a three-year time condition and a three-year performance condition (the “Second Tranche FY 21 Performance-Vesting RSUs”). Assuming the applicable performance conditions are met, the Second Tranche FY 21 Performance-Vesting RSUs will vest at such time, subject to the

  61. Equity Compensation

    | Guidewire Software, Inc. | 49 | 2023 Proxy Statement |

  62. Equity Compensation

    holder’s continued employment with us. For the Second Tranche FY 21 Performance-Vesting RSUs, the performance condition was tied to the achievement of fiscal year 2023 ARR, measured on a constant currency basis using July 31, 2020 exchange rates. The three-year performance period for the Second Tranche FY 21 Performance-Vesting RSUs ended on July 31, 2023. The fiscal year 2023 ARR was achieved at $763 million and based on the applicable performance conditions below, the Second Tranche FY 21 Performance-Vesting RSUs were paid out at 106.3% of target.

  63. Equity Compensation

    | | Threshold (50%) ($) | Target (100%) ($) | Maximum (150%) ($) | Actual Performance ($) | | ARR* | $650M | $750M | $850M | $763M |

  64. Equity Compensation

    *ARR is calculated on a constant currency basis per exchange rates at July 31, 2020 excluding ARR from our HazardHub acquisition. Fiscal Year 2023 Equity Grants Typically, the size and form of the initial equity awards for our executive officers have been established through arm’s-length negotiation at the time the individual executive officer was hired. In formulating these awards our Compensation Committee has considered, among other things, the prospective role and responsibility of the executive officer, the amount of equity-based compensation held by the executive officer at his or her former employer, the cash compensation received by the executive officer, the Compensation Committee’s sense of the competitive market for similar positions (based in part on information supplied by the Compensation Committee’s independent compensation consultant), and the need to create a meaningful opportunity for reward predicated on the creation of long-term stockholder value. Additionally, the Compensation Committee has reviewed the equity holdings of our executive officers annually and granted equity awards in the form of Performance-Vesting RSUs and/or Time-Vesting RSUs to our executive officers to ensure that their overall equity position was consistent with our compensation objectives. For fiscal year 2023, the Compensation Committee did not apply a rigid formula in determining the size of the annual equity awards for the NEOs; however, in making its determination, the Compensation Committee took into account the 50th percentile of our peer group’s annual equity awards to similarly situated executives. In addition, the annual equity awards were split evenly between (i) Performance-Vesting RSUs (50%) and (ii) Time-Vesting RSUs (50%). The Compensation Committee did not strictly benchmark against our peer group, but used its discretion as appropriate, when determining the size of equity awards. In conducting this review and making award determinations in fiscal year 2023, the Compensation Committee also exercised its judgment and discretion and considered several factors, including our overall financial and operational results for the prior fiscal year, the performance of the individual executive officer, the executive officer’s potential to contribute to our long-term strategic goals, his or her role and scope of responsibilities within the Company, his or her individual experience and skills, the Compensation Committee’s sense of competitive market practices for equity compensation (supported in part by information supplied by the Compensation Committee’s independent compensation consultant), and, as applicable, the recommendations of our CEO. Based on these factors, in September 2022, the Compensation Committee approved the Performance-Vesting RSUs and Time-Vesting RSUs to our NEOs as shown in the table below.

  65. Equity Compensation

    | Named Executive Officer | Number of Time-Vesting RSUs | Target Number of Performance-Vesting RSUs | Grant Date Fair Value of RSUs ($) | | Mike Rosenbaum | 59,568 | 59,568 | 7,851,062 | | Jeff Cooper | 27,534 | 27,534 | 3,628,981 | | Priscilla Hung | 27,534 | 27,534 | 3,628,981 | | John Mullen | 24,092 | 24,092 | 3,175,326 | | Winston King | 13,767 | 13,767 | 1,814,491 |

  66. Equity Compensation

    Compensation Mix In determining the amount of base salary, cash bonuses and equity compensation awarded to each NEO, the Compensation Committee does not apply any rigorous percentage of any one element in relation to the overall compensation package. Rather, the Compensation Committee looks at the overall compensation package and the relative amount of each element on an individual basis for each NEO to determine whether such amounts and mix of components further the basic principles and objectives of our overall compensation program.

  67. Equity Compensation

    | Guidewire Software, Inc. | 50 | 2023 Proxy Statement |

  68. Equity Compensation

    Welfare and Other Benefits We have established a tax-qualified Section 401(k) retirement plan for all employees, including NEOs, who satisfy certain eligibility requirements, including requirements relating to age and length of service. Under this plan, employees may elect to defer their current compensation by up to the statutory limit and contribute to the plan. We provide a match for pre-tax contributions equal to fifty cents for every dollar contributed for the first 8% of cash compensation, up to a maximum of $5,000 per participant. We intend for the plan to qualify under Section 401(a) of the Code so that contributions by employees to the plan, and income earned on plan contributions, are not taxable to employees until withdrawn from the plan. In addition, we provide other employee welfare and benefit programs to our executive officers, including the NEOs, on the same basis as all of our full-time employees in the country in which they are resident. These benefits include medical, dental, and vision benefits, medical and dependent care flexible spending accounts, short-term and long-term disability insurance, accidental death and dismemberment insurance and basic life insurance coverage, as well as certain wellness benefits. We design our employee welfare and benefit programs to be affordable and competitive in relation to the market, as well as compliant with applicable laws and practices. We adjust our employee welfare and benefit programs as needed based upon regular monitoring of applicable laws and practices and the competitive market. We do not provide perquisites to our executive officers, except in limited situations where we believe it is appropriate to assist an individual in the performance of his or her duties, to make our executive officers more efficient and effective, and for recruitment and retention purposes. We do not provide any tax gross-ups for perquisites. In the future, we may provide perquisites or other personal benefits in limited circumstances, such as where we believe it is appropriate to assist an individual executive officer in the performance of his or her duties, to make our executive officers more efficient and effective, and for recruitment, motivation, or retention purposes. All future practices with respect to perquisites or other personal benefits will be approved and subject to periodic review by the Compensation Committee. Pension Benefits We do not offer any defined benefit pension plans for our employees. Non-qualified Deferred Compensation We do not offer any non-qualified deferred compensation arrangements for our employees.

  69. Executive Agreements and Termination of Employment Arrangements

    Executive Agreements and Termination of Employment Arrangements We entered into an amended and restated executive agreement with each of Ms. Hung, Mr. Cooper and Mr. King in January 2020, an agreement with Mr. Rosenbaum in August 2019 which was amended in November 2020, and an agreement with Mr. Mullen in February 2022 (collectively, the "Executive Agreements"). The terms of the Executive Agreements are substantially similar. These Executive Agreements provide for at-will employment. In addition, each agreement sets forth the terms and conditions of employment of each of the NEOs, including initial position, initial base salary, initial target annual bonus opportunity and standard employee benefit plan participation. These Executive Agreements also contain provisions that provide for certain payments and benefits in the event of a termination of employment, including an involuntary termination of employment within two months before or 12 months following a change in control of the Company. For a summary of the material terms and conditions of the post-employment compensation terms applicable to our NEOs, see the section titled “Post-Employment Compensation” below. Our philosophy is that outside of a change in control context, severance protections are only appropriate in the event an executive officer is involuntarily terminated by us without cause, and such protections are only provided upon the executive officer's execution of an effective release of claims. In addition, we believe that the occurrence or potential occurrence of a change in control transaction will create uncertainty regarding the continued employment of our executive officers. This uncertainty arises from the fact that many change in control transactions result in significant organizational changes, particularly at the senior executive level. In order to encourage executive officers to remain employed with us during an important time when their prospects for continued employment following the transaction are often uncertain, we provide our executive officers with additional severance protections during a change in control protection period, as mentioned above. We also provide severance protections in connection with a change in control, subject to each executive officer's execution of an effective release of claims against us, to help ensure that executive officers can objectively evaluate change in control transactions that may be in the best interest of our stockholders, despite the potential negative consequences such transactions may have on them personally.

  70. Executive Agreements and Termination of Employment Arrangements

    | Guidewire Software, Inc. | 51 | 2023 Proxy Statement |

  71. Executive Agreements and Termination of Employment Arrangements

    Further, we provide severance protections if an executive officer voluntarily terminates employment with us for good reason in connection with a change in control, subject to the executive officer's execution of an effective release of claims against us, because we believe that a voluntary termination for good reason is essentially equivalent to an involuntary termination by us without cause in those circumstances. We believe that the severance benefits provided to our executive officers under their Executive Agreements are appropriate in light of the severance protections available to similarly-situated executive officers at companies in our peer group and are an important component of each executive officer’s overall compensation as they help us to attract and retain our key executives who could have other job alternatives that may appear to them to be more attractive absent these protections.

  72. Other Compensation Policies

    Other Compensation Policies Stock Ownership Guidelines We have adopted stock ownership guidelines that are applicable to senior executives, including our NEOs. Effective as of March 2021, we amended our stock ownership guidelines to require the CEO and each of the non-CEO executive officers who are subject to reporting obligations pursuant to Section 16 of the Securities Exchange Act of 1934, as amended, to own shares of our common stock equal to at least four times and 1.5 times, respectively, his or her annual base salary, by the first July 31st that occurs following the three-year anniversary of his or her date of hire or promotion or, if later, by July 31, 2023. Only shares of our common stock that are owned or held in the following forms will be considered in determining whether each officer has met the stock ownership requirement: (i) shares owned directly by the officer; (ii) shares “beneficially owned” by the officer that are held in a grantor trust (or similar instrument) for the benefit of the officer and/or his or her immediate family members, but only to the extent that the officer has the power to vote and dispose of such shares; and/or (iii) shares representing the aggregate net value of vested and unexercised in-the-money options. Shares of our common stock underlying unvested options, unvested RSUs, unvested performance-based RSUs and other unvested equity awards will not be considered when determining whether an officer has met the stock ownership requirement. As of July 31, 2023, all our NEOs who have been employed for three or more years have satisfied the ownership requirements. Compensation Recovery Policy In September 2019, we adopted a clawback policy, which was subsequently amended in December 2019 (the “Clawback Policy”), and superseded in September 2023 (as described below). The Clawback Policy provides that if our financial statements are materially restated, whether in part or in their entirety, due to misconduct by one or more covered individuals (i.e., (i) any Section 16 officers and (ii) certain of our C-level employees, senior vice presidents, and sales leadership as designated by the Clawback Policy or agreed upon by our CEO, CFO, and General Counsel), then our Board or Compensation Committee shall have the discretion to recoup a portion of any performance-based compensation that has been paid or distributed to a covered individual during the clawback period (i.e., the three-year period preceding the publication of the restated financials), to the extent such compensation paid or distributed was in excess of what would have been paid under the restated financials. Our Board or the Compensation Committee, in its sole discretion, may also reduce the amount of future compensation, including, without limitation, any bonus or severance, or the future grant or vesting of any equity award, payable to any covered individual by an amount equal to such excess proceeds from performance-based compensation received by the covered individual during the clawback period. Additionally, for any covered individual who is terminated for “cause” (as defined in the Clawback Policy), if our Board determines based on relevant facts and circumstances that the conduct resulting in such for cause termination has caused material, demonstrable reputational harm to the Company, then the Company may require the covered individual to repay a portion of any performance-based compensation that has been paid or distributed to a covered individual during the “for cause clawback period" (i.e., the period from when the first act by the covered individual underlying for cause termination occurred, until such time the covered individual was terminated for cause by the Company). The policy is applicable to all cash and equity-based compensation predicated on the achievement of financial performance goals or financial metrics (excluding any such compensation based on TSR or similar stock price-based metrics). In September 2023, the Board approved two new clawback policies, each effective October 2, 2023. The Compensation Recovery Policy (the "Required Clawback Policy”) complies with the SEC’s newly adopted clawback rules as required under the Dodd-Frank Wall Street Reform and Consumer Protection Act (the “Dodd Frank Act”), and provides that in the event we are required to prepare a “financial restatement” (as defined in the Required Clawback Policy), we shall, subject to certain limited exceptions as described in the Required Clawback Policy, recover certain incentive based compensation from “covered persons” (i.e., “executive officers”, defined to include (i) the president, principal financial officer, principal accounting officer (or if there is no such accounting officer, the controller), any vice president in charge of a principal business unit, division or function, or any officer or person who performs a policy making functions and (ii) who served during the performance period applicable to “incentive based compensation” and received “incentive based compensation” after beginning service in any such role). Compensation that shall be recovered under the Required Clawback Policy generally includes “incentive based compensation” received during the three-year period prior to the “restatement date” (as defined in the Required Clawback Policy) that exceeds

  73. Other Compensation Policies

    the amount that otherwise would have been received by the “covered person” had such compensation been determined based on the restated amounts in the financial restatement. Under the Required Clawback Policy, “incentive based compensation” includes any cash or equity compensation that is granted, earned, or vested based, in whole or in part, upon the attainment of a financial reporting measure. The Supplemental Compensation Recovery Policy (the “Supplemental Clawback Policy”) amends and restates the Clawback Policy and provides for the discretionary recovery of “incentive based compensation” from certain “covered persons” (i.e., (i) “executive officers” and (ii) certain of our C-level employees, senior vice presidents, and sales leadership as designated by the Supplemental Clawback Policy (“senior officers”)) in addition to any recovery required under the Required Clawback Policy. Under the Supplemental Clawback Policy, “incentive based compensation” includes, similar to the Required Clawback Policy, any cash or equity compensation that is granted, earned, or vested based, in whole or in part, upon the attainment of a financial reporting measure and also includes other equity-based compensation such as stock options, restricted stock awards, restricted stock units, and stock appreciation rights. Additionally, for any “covered person” who is terminated for “cause” (as defined in the Supplemental Clawback Policy) or who resigns, but is later determined that he or she could have been terminated for cause, if our Board determines based on relevant facts and circumstances that the conduct resulting in such for cause termination (or conduct which could have resulted in such for cause termination) has caused material, demonstrable reputational harm to the Company, then the Board may require such “covered person” to repay a portion of any “incentive-based compensation” received by such “covered person” during the “for cause clawback period" (i.e., the period from when the first act by the covered individual underlying for cause termination occurred, until such time the covered individual was terminated for cause by the Company or until such time the “covered person” resigned from the Company, as applicable). Under both the Required Clawback Policy and the Supplemental Clawback Policy, “incentive based compensation” received by a “covered person” prior October 2, 2023 is subject to the Clawback Policy and “incentive based compensation” received by a “covered person” on or after October 2, 2023 is subject to the Required Clawback Policy and/or the Supplemental Clawback Policy, as applicable. In addition, our 2011 Stock Plan provides that if we are required to prepare an accounting restatement due to our material noncompliance, as a result of misconduct, with any financial reporting requirement under the securities laws, then any equity award holder who is an individual subject to automatic forfeiture under Section 304 of the Sarbanes-Oxley Act of 2002 must reimburse us for the amount of any equity award received by such individual under such plans during the 12-month period following the first public issuance or filing with the SEC, as the case may be, of the financial document embodying such financial reporting requirement. Furthermore, our Stock Plan provides that all awards thereunder will be subject to the Company’s clawback policy in effect, from time to time. Derivatives Trading and Hedging Policy Our NEOs, employees, and directors are subject to our insider trading policy. Under this policy all of our executive officers, employees and directors are prohibited from engaging in transactions in publicly-traded options and other derivative securities with respect to our securities, including any hedging or similar transactions. Anti-Pledging Policy Under our insider trading policy, all of our executive officers, employees, and directors are prohibited from pledging our securities as collateral for loans. Equity Award Grant Policy In March 2021, we adopted an Equity Award Grant Policy that sets forth the process and timing for us to follow when we grant equity awards for shares of our common stock to our employees, including our executive officers, pursuant to any of our equity compensation plans. The policy was amended and restated in September 2023. Pursuant to the policy (as amended and restated), all grants of equity awards must be approved in advance by our Board, the Compensation Committee or, subject to the delegation requirements in the policy, the Equity Grant Committee. The Equity Grant Committee is currently comprised of our CEO, CFO, and General Counsel. The equity award granting authority delegated to the Equity Grant Committee applies to non-executive employees and covers awards of RSUs within specific ranges set forth in the policy, which will be updated annually by the Compensation Committee. The Equity Award Grant Policy sets forth that equity awards are generally granted on the following regularly scheduled basis: •Equity awards granted in connection with the hiring of a new employee or the promotion of an existing employee will be on a quarterly basis and be effective on the date on which such award is approved by the Board, the Compensation Committee or the Equity Grant Committee.

  74. Other Compensation Policies

    •Equity awards granted to existing employees (other than in connection with a promotion) will generally be granted, if at all, on an annual basis effective on the date on which such award is approved by the Board, the Compensation Committee or the Equity Grant Committee. Our Board and the Compensation Committee retain the discretion to grant equity awards at other times to the extent appropriate in light of the circumstances of such awards. In addition, the policy sets forth the manner in which our equity awards will be priced. If an award of restricted stock or restricted stock units is denominated in dollars, the number of shares subject to the award will be determined by dividing the dollar value by the average closing market price on the NYSE of a share of our common stock over the ten trading days ending two trading days immediately preceding the effective date of grant, with such total number of shares rounded up to the nearest whole share. The exercise price of all stock options will be at equal to the closing market price on the NYSE of a share of our common stock on the effective date of grant. If the amount of a stock option award is to be determined by reference to a fair value calculated under Financial Accounting Standards Board Accounting Standard Codification Topic 718, Stock Compensation, or FASB ASC Topic 718, then the number of shares to be subject to such stock option will be determined based on such fair value, and the exercise price determined in accordance with the preceding sentence and the approved valuation assumptions, subject to any other limits on the number of shares that may be subject to such stock option.

  75. Tax and Accounting Considerations

    Tax and Accounting Considerations Deductibility of Executive Compensation Section 162(m) of the Code generally disallows public companies a tax deduction for federal income tax purposes of remuneration in excess of $1 million paid to certain specified executive officers, including a public corporation’s chief executive officer, chief financial officer and each of the three other most highly compensated executive officers whose compensation is required to be disclosed to stockholders under the Exchange Act. Pursuant to the Tax Cuts and Jobs Act of 2017, which was signed into law on December 22, 2017 (the “Tax Act”), for years beginning after December 31, 2017, all remuneration in excess of $1 million paid to a specified executive is not deductible. In addition, under the Tax Act, once an executive becomes a "covered employee" under Section 162(m) of the Code, the individual will continue to be a “covered employee” as long as he or she remains employed by the company. In approving the amount and form of compensation for our executive officers, the Compensation Committee is mindful of the benefit of receiving full deductibility of compensation; however, our Compensation Committee believes that we should not be constrained by the requirements of Section 162(m) of the Code, where such requirements would impair our flexibility in compensating our executive officers in a manner that can best promote our corporate objectives and attract and retain executive talent. Our Compensation Committee monitors the application of Section 162(m) of the Code, as well as developments under Section 162(m) of the Code, and balances the benefits of potentially paying compensation that is deductible under Section 162(m) with our need to have the flexibility to maintain compensation plans that are designed to promote our objectives. Taxation of “Parachute” Payments Sections 280G and 4999 of the Code provide that executive officers and directors who hold significant equity interests and certain other service providers may be subject to significant additional taxes if they receive payments or benefits in connection with a change in control of the company that exceeds certain prescribed limits, and that the company (or a successor) may forfeit a deduction on the amounts subject to this additional tax. We have not agreed to provide any executive officer, including any NEO, with a “gross-up” or other reimbursement payment for any tax liability that the executive officer might owe as a result of the application of Sections 280G or 4999 of the Code. Accounting for Stock-Based Compensation We follow FASB ASC Topic 718 for our stock-based compensation awards. FASB ASC Topic 718 requires companies to measure the compensation expense for all share-based payment awards made to employees and directors, based on the grant date “fair value” of these awards. This calculation is performed for accounting purposes and reported in the compensation tables below, even though our executive officers may never realize any value from their awards. FASB ASC Topic 718 also requires companies to recognize the compensation cost of their stock-based compensation awards in their income statements over the period that an executive officer is required to render service in exchange for the option or other stock-based award.

  76. Summary Compensation Table

    Summary Compensation Table The following table summarizes the compensation that we paid to, or that was earned by or granted to, each of the NEOs during our fiscal years 2023, 2022, and 2021.

  77. Summary Compensation Table

    | Name and Principal Position | Year | Base Salary ($) | Bonus ($) | Stock Awards ($)(1) | Non-Equity Incentive Plan Compensation ($) | All Other Compensation ($)(2) | Total ($) | | Mike Rosenbaum Chief Executive Officer | 2023 | 750,000 | — | 7,851,062 | 943,500 | 5,930 | 9,550,492 | | | 2022 | 750,000 | — | 8,474,034 | 855,000 | 5,944 | 10,084,978 | | | 2021 | 750,000 | — | 6,627,872 | 851,250 | 5,712 | 8,234,834 | | Jeff Cooper Chief Financial Officer | 2023 | 400,000 | — | 3,628,981 | 377,400 | 5,748 | 4,412,129 | | | 2022 | 397,833 | — | 3,720,580 | 329,084 | 5,752 | 4,453,249 | | | 2021 | 387,000 | — | 1,117,600 | 263,547 | 5,592 | 1,773,739 | | Priscilla Hung President and Chief Operating Officer | 2023 | 425,000 | — | 3,628,981 | 400,988 | 5,793 | 4,460,762 | | | 2022 | 421,667 | — | 4,509,808 | 360,518 | 5,792 | 5,297,785 | | | 2021 | 405,000 | — | 3,352,800 | 344,756 | 5,611 | 4,108,167 | | John Mullen(3) President and Chief Revenue Officer | 2023 | 500,000 | — | 3,175,326 | 629,000 | 5,930 | 4,310,256 | | | 2022 | 246,474 | 750,000 | 10,150,676 | — | 5,465 | 11,152,615 | | Winston King Chief Administrative Officer, General Counsel, and Secretary | 2023 | 390,000 | — | 1,814,491 | 367,965 | 5,729 | 2,578,185 | | | 2022 | 383,333 | — | 2,254,904 | 311,065 | 5,713 | 2,955,015 | | | 2021 | 350,000 | — | 2,011,680 | 198,625 | 5,552 | 2,565,857 |

  78. Summary Compensation Table

    (1)The amounts shown reflect the aggregate grant date fair value of RSUs granted, determined in accordance with FASB ASC Topic 718. These amounts do not represent the actual amounts paid to or realized by the NEOs during the fiscal years presented. Pursuant to SEC rules, these amounts exclude the impact of estimated forfeitures related to service-based vesting conditions. See Note 10 of the consolidated financial statements in our 2023 Annual Report, regarding assumptions underlying valuation of equity awards for fiscal years 2023, 2022, and 2021. Details regarding equity awards that are still outstanding can be found in the “Outstanding Equity Awards at Fiscal Year End” table. The aggregate grant fair value of the Performance-Vesting RSUs at the maximum level of achievement for fiscal year 2023 and fiscal year 2025 is as follows for Messrs. Rosenbaum, Cooper, Mullen, and King, and Ms. Hung: $5,888,231; $2,721,670; $2,381,362; $1,360,835; and $2,721,670, respectively. (2)The amounts reported in the “All Other Compensation” column consist of life insurance premiums and 401(k) matching contributions paid by the Company on behalf of each NEO. Fiscal year 2023 amounts are comprised of $5,000 of 401(k) matching contributions for Messrs. Rosenbaum, Cooper, Mullen, and King, and Ms. Hung, and the following life insurance premiums for Messrs. Rosenbaum, Cooper, Mullen, and King, and Ms. Hung of $930, $748, $793, $930, and $729, respectively. (3)Mr. Mullen was not a NEO prior to fiscal year 2022. Mr. Mullen commenced employment with us on February 3, 2022.

  79. Summary Compensation Table

    | Guidewire Software, Inc. | 55 | 2023 Proxy Statement |

  80. Grants of Plan-Based Awards

    Grants of Plan-Based Awards The following table presents information concerning grants of plan-based awards to each of the NEOs during fiscal year 2023.

  81. Grants of Plan-Based Awards

    | | | Estimated Future Payouts Under Non-Equity Incentive Plan Awards(1) | | | Estimated Future Payouts Under Equity Incentive Plan Awards | | | All Other Stock Awards: Number of Shares of Stock or Units (#) | Grant Date Fair Value of Stock and Option Awards ($) | | Name | Grant Date(2) | Threshold ($) | Target ($) | Maximum ($) | Threshold (#) | Target (#) | Maximum (#) | | | | Mike Rosenbaum | | | | | | | | | | | Annual Bonus Opportunity | | 281,250 | 750,000 | 1,218,750 | | | | | | | Performance-Vesting RSUs(3) | 9/15/2022 | | | | 14,892 | 29,783 | 44,675 | | 1,962,700 | | Performance-Vesting RSUs(4) | 9/15/2022 | | | | 14,893 | 29,785 | 44,678 | | 1,962,832 | | Time-Vesting RSUs(5) | 9/15/2022 | | | | | | | 59,568 | 3,925,531 | | Jeff Cooper | | | | | | | | | | | Annual Bonus Opportunity | | 112,500 | 300,000 | 487,500 | | | | | | | Performance-Vesting RSUs(3) | 9/15/2022 | | | | 6,883 | 13,766 | 20,649 | | 907,179 | | Performance-Vesting RSUs(4) | 9/15/2022 | | | | 6,884 | 13,768 | 20,652 | | 907,311 | | Time-Vesting RSUs(5) | 9/15/2022 | | | | | | | 27,534 | 1,814,491 | | Priscilla Hung | | | | | | | | | | | Annual Bonus Opportunity | | 119,531 | 318,750 | 517,969 | | | | | | | Performance-Vesting RSUs(3) | 9/15/2022 | | | | 6,883 | 13,766 | 20,649 | | 907,179 | | Performance-Vesting RSUs(4) | 9/15/2022 | | | | 6,884 | 13,768 | 20,652 | | 907,311 | | Time-Vesting RSUs(5) | 9/15/2022 | | | | | | | 27,534 | 1,814,491 | | John Mullen | | | | | | | | | | | Annual Bonus Opportunity | | 187,500 | 500,000 | 812,500 | | | | | | | Performance-Vesting RSUs(3) | 9/15/2022 | | | | 6,023 | 12,045 | 18,068 | | 793,766 | | Performance-Vesting RSUs(4) | 9/15/2022 | | | | 6,024 | 12,047 | 18,071 | | 793,897 | | Time-Vesting RSUs(5) | 9/15/2022 | | | | | | | 24,092 | 1,587,663 | | Winston King | | | | | | | | | | | Annual Bonus Opportunity | | 109,688 | 292,500 | 475,313 | | | | | | | Performance-Vesting RSUs(3) | 9/15/2022 | | | | 3,442 | 6,883 | 10,325 | | 453,590 | | Performance-Vesting RSUs(4) | 9/15/2022 | | | | 3,442 | 6,884 | 10,326 | | 453,656 | | Time-Vesting RSUs(5) | 9/15/2022 | | | | | | | 13,767 | 907,245 |

  82. Grants of Plan-Based Awards

    (1)The amounts shown represent the threshold, target, and maximum amount of potential cash bonus awards provided for under the Bonus Plan. The target amounts are pre-established as a fixed dollar amount. The maximum amounts represent the greatest payout that could have been made if the pre-established performance level was exceeded. Under the Bonus Plan the maximum amount payable was equal to 150% (at 75% weighting) and 200% (at 25% weighting) of the target

  83. Grants of Plan-Based Awards

    | Guidewire Software, Inc. | 56 | 2023 Proxy Statement |

  84. Grants of Plan-Based Awards

    amount; however, payout above is at the discretion of our Board. If the threshold amount was achieved, then 50% (at 75% weighting) and 0% (at 25% weighting) of the target amount was payable and if the target amount was achieved, then 100% of the target amount was payable. If achievement is less than the threshold amount for all the performance criteria, 0% was payable. (2)Each grant was approved by our Compensation Committee on the grant date indicated. (3)Represents awards of First Tranche Performance-Vesting RSUs granted under our Stock Plan, as described under "Equity Compensation — Performance-Vesting RSUs" above. In the case of First Tranche Performance-Vesting RSUs, the aggregate grant date fair value is reported for the probable outcome, which for this purpose is estimated as 100% target achievement. (4)Represents awards of Second Tranche Performance-Vesting RSUs granted under our Stock Plan, as described under "Equity Compensation — Performance Vesting RSUs" above. In the case of Second Tranche Performance-Vesting RSUs, the aggregate grant date fair value is reported for the probable outcome, which for this purpose is estimated as 100% target achievement. (5)Time-Vesting RSUs granted under our Stock Plan generally vest quarterly over four years, subject to the executive officer's continued employment with the Company through each applicable vesting date.

  85. Grants of Plan-Based Awards

    | Guidewire Software, Inc. | 57 | 2023 Proxy Statement |

  86. Outstanding Equity Awards at Fiscal 2023 Year End

    Outstanding Equity Awards at Fiscal 2023 Year End The following table provides information regarding outstanding equity awards, including stock options and RSUs, and applicable market values at the end of fiscal year 2023.

  87. Outstanding Equity Awards at Fiscal 2023 Year End

    | | | | | | | Stock Awards | | | | | | | Option Awards | | | | Time-Based | | Performance-Based | | | Name | Grant Date | Number of Securities Underlying Unexercised Options (#) Exercisable | Number of Securities Underlying Unexercised Options (#) Unexercisable | Option Exercise Price ($) | Option Expiration Date | Number of Shares or Units of Stock that Have Not Vested (#) | Market Value of Shares or Units of Stock that Have Not Vested(1) ($) | Equity Incentive Plan Awards: Number of Unearned Shares, Units or Other Rights That Have Not Vested (#) | Equity Incentive Plan Awards: Market or Payout Value of Unearned Shares, Units or Other Rights That Have Not Vested(1) ($) | | Mike Rosenbaum | 9/6/2019(2) | — | — | — | — | 4,606 | 390,681 | — | — | | | 9/6/2019(3) | — | — | — | — | 2,555 | 216,715 | — | — | | | 9/10/2020(4) | — | — | — | — | 9,510 | 806,638 | — | — | | | 9/10/2020(5) | — | — | — | — | 21,465 | 1,820,661 | — | — | | | 9/15/2021(4) | — | — | — | — | 19,822 | 1,681,302 | — | — | | | 9/15/2021(6) | — | — | — | — | 14,330 | 1,215,471 | 17,619 | 1,494,444 | | | 9/15/2022(4) | — | — | — | — | 48,399 | 4,105,203 | — | — | | | 9/15/2022(7) | — | — | — | — | 30,320 | 2,571,742 | 29,785 | 2,526,364 | | Jeff Cooper | 9/6/2019(4) | — | — | — | — | 142 | 12,044 | — | — | | | 6/9/2020(4) | — | — | — | — | 7,218 | 612,231 | — | — | | | 9/9/2020(4) | — | — | — | — | 1,563 | 132,574 | — | — | | | 9/9/2020(5) | — | — | — | — | 3,528 | 299,245 | — | — | | | 9/14/2021(4) | — | — | — | — | 8,722 | 739,800 | — | — | | | 9/14/2021(6) | — | — | — | — | 6,304 | 534,705 | 7,753 | 657,609 | | | 9/15/2022(4) | — | — | — | — | 22,372 | 1,897,593 | — | — | | | 9/15/2022(7) | — | — | — | — | 14,015 | 1,188,752 | 13,768 | 1,167,802 | | Priscilla Hung | 9/6/2019(4) | — | — | — | — | 782 | 66,329 | — | — | | | 9/6/2019(3) | — | — | — | — | 342 | 29,008 | — | — | | | 9/9/2020(4) | — | — | — | — | 4,688 | 397,636 | — | — | | | 9/9/2020(5) | — | — | — | — | 10,581 | 897,480 | — | — | | | 9/14/2021(4) | — | — | — | — | 10,572 | 896,717 | — | — | | | 9/14/2021(6) | — | — | — | — | 7,643 | 648,279 | 9,397 | 797,054 | | | 9/15/2022(4) | — | — | — | — | 22,372 | 1,897,593 | — | — | | | 9/15/2022(7) | — | — | — | — | 14,015 | 1,188,752 | 13,768 | 1,167,802 | | John Mullen | 3/15/2022(8) | — | — | — | — | 82,150 | 6,967,963 | — | — | | | 9/15/2022(4) | — | — | — | — | 19,575 | 1,660,352 | — | — | | | 9/15/2022(7) | — | — | — | — | 12,261 | 1,039,978 | 12,047 | 1,021,827 |

  88. Outstanding Equity Awards at Fiscal 2023 Year End

    | Guidewire Software, Inc. | 58 | 2023 Proxy Statement |

  89. Outstanding Equity Awards at Fiscal 2023 Year End

    | | | | | | | Stock Awards | | | | | | | Option Awards | | | | Time-Based | | Performance-Based | | | Name | Grant Date | Number of Securities Underlying Unexercised Options (#) Exercisable | Number of Securities Underlying Unexercised Options (#) Unexercisable | Option Exercise Price ($) | Option Expiration Date | Number of Shares or Units of Stock that Have Not Vested (#) | Market Value of Shares or Units of Stock that Have Not Vested(1) ($) | Equity Incentive Plan Awards: Number of Unearned Shares, Units or Other Rights That Have Not Vested (#) | Equity Incentive Plan Awards: Market or Payout Value of Unearned Shares, Units or Other Rights That Have Not Vested(1) ($) | | Winston King | 9/13/2013(9) | 42 | — | 46.77 | 9/13/2023 | — | — | — | — | | | 9/4/2014(9) | 105 | — | 45.27 | 9/4/2024 | — | — | — | — | | | 9/6/2019(4) | — | — | — | — | 438 | 37,151 | — | — | | | 9/6/2019(3) | — | — | — | — | 191 | 16,201 | — | — | | | 9/9/2020(4) | — | — | — | — | 2,813 | 238,599 | — | — | | | 9/9/2020(5) | — | — | — | — | 6,349 | 538,522 | — | — | | | 9/14/2021(4) | — | — | — | — | 5,286 | 448,359 | — | — | | | 9/14/2021(6) | — | — | — | — | 3,822 | 324,182 | 4,699 | 398,569 | | | 9/15/2022(4) | — | — | — | — | 11,186 | 948,797 | — | — | | | 9/15/2022(7) | — | — | — | — | 7,006 | 594,249 | 6,884 | 583,901 |

  90. Outstanding Equity Awards at Fiscal 2023 Year End

    (1)The amounts shown are based on a price of $84.82 per share, which was the closing price of our common stock as reported on the NYSE on July 31, 2023. (2)Time-Vesting RSUs vest over four years (25% cliff vest on the first anniversary of September 15, 2019, then in equal quarterly installments thereafter). (3)Performance-Vesting RSUs vest over four years (25% after 1 year, then in equal quarterly installments thereafter), commencing on September 15, 2019, assuming attainment of pre-defined financial results for fiscal year 2020, which were attained at 73%. (4)Time-Vesting RSUs vest in equal quarterly installments over four years, commencing on the grant date. (5)Performance-Vesting RSUs vest over three years (33% of 50% of the shares vest after 1 year, then in equal annual installments over 2 years), commencing on September 15, 2020, assuming attainment of predefined financial results for fiscal year 2021, which were attained at 104.3%. The remaining 50% of the shares will vest in year 3 assuming attainment of predefined financial results for fiscal year 2023, which were attained at 106.3%. (6)Performance-Vesting RSUs vest over three years (33% of 50% of the shares vest after 1 year, then in equal annual installments over 2 years), commencing on September 15, 2021, assuming attainment of predefined financial results for fiscal year 2022, which were attained at 122%. The remaining 50% of the shares will vest in year 3 assuming attainment of predefined financial results for fiscal year 2024. (7)Performance-Vesting RSUs vest over three years (33% of 50% of the shares vest after 1 year, then in equal annual installments over 2 years), commencing on September 15, 2022, assuming attainment of predefined financial results for fiscal year 2023, which were attained at 101.8%. The remaining 50% of the shares will vest in year 3 assuming attainment of predefined financial results for fiscal year 2025. (8)Time-Vesting RSUs vest over four years (25% cliff vest on the first anniversary of March 15, 2022, then in equal quarterly installments thereafter). (9)The time-based vesting condition has been met and the option is fully vested and exercisable.

  91. Outstanding Equity Awards at Fiscal 2023 Year End

    | Guidewire Software, Inc. | 59 | 2023 Proxy Statement |

  92. Option Exercises and Stock Vested During Fiscal Year 2023

    Option Exercises and Stock Vested During Fiscal Year 2023 The following table presents certain information concerning the exercise of options by each of the NEOs during the fiscal year ended July 31, 2023, as well as information regarding stock awards that vested during the fiscal year.

  93. Option Exercises and Stock Vested During Fiscal Year 2023

    | | Options Awards | | Stock Awards | | | Name | Number of Shares Acquired on Exercise (#) | Value Realized on Exercise ($)(1) | Number of Shares Acquired on Vesting (#)(2) | Value Realized on Vesting ($)(3) | | Mike Rosenbaum | — | — | 68,685 | 4,781,935 | | Jeff Cooper | — | — | 22,771 | 1,586,709 | | Priscilla Hung | — | — | 28,079 | 1,948,407 | | John Mullen | — | — | 41,857 | 3,098,766 | | Winston King | 192 | 6,252 | 15,155 | 1,050,837 |

  94. Option Exercises and Stock Vested During Fiscal Year 2023

    (1)The value realized upon the exercise of stock options is calculated by (i) subtracting the option exercise price from the market price on the date of exercise to get the realized value per share, and (ii) multiplying the realized value per share by the number of shares underlying options exercised. (2)Represents shares of common stock released during fiscal year 2023. (3)The value realized upon vesting of RSUs is calculated by multiplying the number of RSUs vested by the closing price of common stock on the day prior to the vesting date.

  95. Option Exercises and Stock Vested During Fiscal Year 2023

    | Guidewire Software, Inc. | 60 | 2023 Proxy Statement |

  96. Potential Payments upon Termination or Change in Control

    Potential Payments upon Termination or Change in Control The table below reflects, as applicable, cash severance, equity acceleration, and continuation of health benefits payable to our NEOs in connection with (1) the termination of his or her employment relationship without cause not in connection with a change in control, (2) upon a change in control of our Company and no termination of employment (assuming that all equity awards will not be assumed or continued or substituted by the successor entity), and (3) upon an involuntary termination of employment (i.e., a termination without cause or resignation for good reason) within the period commencing two months prior to and ending 12 months following a change in control (assuming that all equity awards will be assumed or continued or substituted by the successor entity), assuming for each of (1), (2), and (3) that the applicable triggering event(s) occurred on July 31, 2023. See section above titled “Post-Employment Compensation.”

  97. Potential Payments upon Termination or Change in Control

    | Name | Benefit | Termination without Cause Not in Connection with a Change in Control ($) | Change in Control, No Termination of Employment, and No Assumption ($) | Involuntary Termination in Connection with a Change in Control ($) | | Mike Rosenbaum | Cash Severance | 1,500,000(1) | — | 2,250,000(2) | | | Equity Acceleration | — | 16,829,221(3) | 16,829,221(3) | | | Health Benefits | 26,055(4) | — | 39,082(5) | | | Total | 1,526,055 | 16,829,221 | 19,118,303 | | Jeff Cooper | Cash Severance | 400,000(6) | — | 700,000(7) | | | Equity Acceleration | — | 7,242,356(3) | 7,242,356(3) | | | Health Benefits | 18,829(4) | — | 18,829(4) | | | Total | 418,829 | 7,242,356 | 7,961,185 | | Priscilla Hung | Cash Severance | 425,000(6) | — | 743,750(7) | | | Equity Acceleration | — | 7,986,651(3) | 7,986,651(3) | | | Health Benefits | 18,494(4) | — | 18,494(4) | | | Total | 443,494 | 7,986,651 | 8,748,895 | | John Mullen | Cash Severance | 500,000(6) | — | 1,000,000(7) | | | Equity Acceleration | 1,393,593(8) | 10,690,119(3) | 10,690,119(3) | | | Health Benefits | 26,055(4) | — | 26,055(4) | | | Total | 1,919,648 | 10,690,119 | 11,716,174 | | Winston King | Cash Severance | 390,000(6) | — | 550,110(7) | | | Equity Acceleration | — | 4,128,529(3) | 4,128,529(3) | | | Health Benefits | 25,783(4) | — | 25,783(4) | | | Total | 415,783 | 4,128,529 | 4,704,422 |

  98. Potential Payments upon Termination or Change in Control

    (1)Represents 12 months' continuation of Mr. Rosenbaum's base salary and payment of one times his target annual bonus opportunity. (2)Represents 1.5 times the sum of each of Mr. Rosenbaum's base salary and target annual bonus opportunity. (3)Represents, as applicable, the value of the acceleration of vesting of 100% of the executive's unvested Time-Vesting RSUs, 1/3rd of the first tranche FY 2021 performance-vesting RSUs at 104.3% attainment, the second tranche FY 2021

  99. Potential Payments upon Termination or Change in Control

    | Guidewire Software, Inc. | 62 | 2023 Proxy Statement |

  100. Potential Payments upon Termination or Change in Control

    performance-vesting RSUs at 106.3% attainment, 2/3rds of the first tranche FY 2022 performance-vesting RSUs at 122% attainment, the second tranche FY 2022 performance-vesting RSUs at 100% attainment, the first tranche FY 2023 performance-vesting RSUs at 101.8%, and the second tranche FY 2023 performance-vesting RSUs at 100% attainment, all based on the closing price of our common stock as reported on the NYSE on July 31, 2023, which was $84.82. (4)Represents 12 months of payment of COBRA premiums for the executive. (5)Represents 18 months of payment of COBRA premiums for Mr. Rosenbaum. (6)Represents 12 months' continuation of the executive's base salary. (7)Represents one times the sum of the executive's base salary and target annual bonus opportunity. (8)Represents the value of the acceleration of vesting of 20% of Mr. Mullen’s outstanding initial Time-Vesting RSUs, based on the closing price of our common stock as reported on the NYSE on July 31, 2023, which was $84.82.

  101. Potential Payments upon Termination or Change in Control

    | Guidewire Software, Inc. | 63 | 2023 Proxy Statement |

  102. CEO Pay Ratio

    CEO Pay Ratio Our compensation and benefits philosophy and the overall structure of our compensation and benefit programs are broadly similar across the organization to encourage and reward all employees who contribute to our success. We strive to ensure the pay of every employee reflects the level of their job impact and responsibilities and is competitive within our peer group. Our ongoing commitment to pay equity is critical to our success in supporting a diverse workforce with opportunities for all employees to grow, develop, and contribute. Under rules adopted pursuant to the Dodd-Frank Act, we are required to calculate and disclose the total compensation paid to our median paid employee, as well as the ratio of the total compensation paid to the median employee as compared to the total compensation paid to our CEO (the “CEO Pay Ratio”). The paragraphs that follow describe our methodology and the resulting CEO Pay Ratio.

  103. Methodology and Pay Ratio

    Methodology and Pay Ratio Once the median employee was identified, we calculated the median employee’s annual total compensation in accordance with the requirements of the Summary Compensation Table. Our median employee compensation as calculated using Summary Compensation Table requirements (excluding health and welfare benefits) was $159,207. Our CEO’s compensation as reported in the Summary Compensation Table (excluding health and welfare benefits) was $9,549,562. Therefore, our CEO Pay Ratio is approximately 60:1. This information is being provided for compliance purposes and is a reasonable estimate calculated in a manner consistent with SEC rules, based on our internal records and the methodology described above. The SEC rules for identifying the median compensated employee allow companies to adopt a variety of methodologies, to apply certain exclusions and to make reasonable estimates and assumptions that reflect their employee populations and compensation practices. Accordingly, the pay ratio reported by other companies may not be comparable to the pay ratio reported above, as other companies have different employee populations and compensation practices and may use different methodologies, exclusions, estimates and assumptions in calculating their own pay ratios. Neither the Compensation Committee nor management of the company used the CEO Pay Ratio measure in making compensation decisions.

  104. Methodology and Pay Ratio

    | Guidewire Software, Inc. | 64 | 2023 Proxy Statement |

  105. Pay Versus Performance

    Pay Versus Performance

  106. Pay Versus Performance Table

    Pay Versus Performance Table The following table sets forth the pay versus performance disclosures required by Section 953(a) of the Dodd-Frank Act and Item 402(v) of Regulation S-K, for each of the last three completed fiscal years. Because of the emphasis our executive compensation program places on equity compensation, as discussed in “Compensation Discussion and Analysis,” there may be large increases or decreases in the calculation of “compensation actually paid” to our NEOs on a year-to-year basis due to fluctuation in our stock price. This disclosure has been prepared in accordance with Item 402(v) of Regulation S-K and does not necessarily reflect value actually realized by our NEOs.

  107. Pay Versus Performance Table

    | | | | | | Value of Initial Fixed $100 Investment Based on: (4) | | | | | Fiscal Year | Summary Compensation Table Total for CEO ($)(1) | Compensation Actually Paid to CEO ($)(2) | Average Summary Compensation Table Total for Non-CEO NEOs ($)(3) | Average Compensation Actually Paid to Non-CEO NEOs ($)(2) | Company Total Stockholder Return | Peer Group Total Stockholder Return (5) | Net Income (in thousands) | Annual Recurring Revenue (in millions)(6) | | 2023 | 9,550,492 | 11,214,092 | 3,940,333 | 4,859,553 | 72.09 | 123.74 | (111,855) | 761 | | 2022 | 10,084,978 | 2,928,935 | 6,354,350 | 3,092,856 | 66.05 | 104.47 | (180,431) | 683 | | 2021 | 8,234,834 | 7,315,842 | 3,007,199 | 2,810,775 | 97.91 | 147.98 | (66,507) | 575 |

  108. Pay Versus Performance Table

    (1)Our principal executive officer for all covered fiscal years was our CEO, Mr. Rosenbaum, and we have referred to him as our CEO throughout this disclosure. (2)We have made adjustments to the Summary Compensation Table totals—as prescribed by Item 402(v) of Regulation S-K—to calculate the amounts disclosed above as “compensation actually paid.” These adjustments are disclosed in the tables following footnote (6) below under the caption, “Adjustments to Determine Compensation Actually Paid.” Fair value or change in fair value, as applicable, of equity awards in the “Compensation Actually Paid” columns was determined by reference to: (i) for Time-Vesting RSUs, the closing price per share on the applicable year-end date(s) or, in the case of vesting dates, the closing price per share on the applicable vesting date(s); (ii) for Performance-Vesting RSUs, the same valuation methodology as Time-Vesting RSUs in the immediately preceding clause, except that the year-end values are multiplied by the probability of achievement of the applicable performance objective as of the applicable date; and (iii) for RSUs subject to performance-based vesting conditions tied to total stockholder return as granted prior to fiscal year 2021, estimated fair values of such unvested awards using a Monte Carlo simulation model as of each relevant measurement date for fiscal years 2021 to 2023. For additional information on the assumptions used to calculate the valuation of these awards, see the Notes to Consolidated Financial Statements in our Annual Report on Form 10-K for the fiscal year ended July 31, 2023 and prior fiscal years. (3)Our non-CEO NEOs for the fiscal years ended July 31, 2021, July 31, 2022 and July 31, 2023 are set forth in the second summary table provided below under the caption, “Adjustments to Determine Compensation Actually Paid.” (4)Assumes $100 invested on July 31, 2020 in stock or index, including reinvestment of dividends. (5)Our peer group (the “Peer Group”) is comprised of the S&P Software & Services Select Industry Index, as disclosed in our annual report pursuant to Section 229.201(e)(1)(ii) of Regulation S-K. (6)We selected Annual Recurring Revenue (on a constant currency basis) as the Company-Selected Measure given its inclusion in our quarterly earnings releases and as a financial target in our bonus program and certain equity awards for our management team.

  109. Pay Versus Performance Table

    | Guidewire Software, Inc. | 65 | 2023 Proxy Statement |

  110. Adjustments to Determine Compensation Actually Paid

    Adjustments to Determine Compensation Actually Paid Compensation actually paid to our CEO represents the “Total” compensation reported in the Summary Compensation Table for the applicable fiscal year, as adjusted as follows:

  111. Adjustments to Determine Compensation Actually Paid

    | | 2021 | 2022 | 2023 | | Summary Compensation Table Total for CEO(1) | $8,234,834 | $10,084,978 | $9,550,492 | | Subtract Grant Date Fair Value of Option Awards and Stock Awards Granted in Fiscal Year(2) | $(6,627,872) | $(8,474,034) | $(7,851,062) | | Add Fair Value at Fiscal Year-End of Outstanding and Unvested Option Awards and Stock Awards Granted in Fiscal Year(3) | $6,480,263 | $5,558,182 | $9,157,761 | | Adjust for Change in Fair Value of Outstanding and Unvested Option Awards and Stock Awards Granted in Prior Fiscal Years(3) | $(1,071,147) | $(4,253,689) | $403,027 | | Adjust for Fair Value at Vesting of Option Awards and Stock Awards Granted in Fiscal Year That Vested During Fiscal Year(3) | $656,767 | $600,823 | $795,456 | | Adjust for Change in Fair Value as of Vesting Date of Option Awards and Stock Awards Granted in Prior Fiscal Years For Which Applicable Vesting Conditions Were Satisfied During Fiscal Year(3) | $(357,003) | $(587,325) | $(841,582) | | Subtract Fair Value as of Prior Fiscal Year-End of Option Awards and Stock Awards Granted in Prior Fiscal Years That Failed to Meet Applicable Vesting Conditions During Fiscal Year(3) | $— | $— | $— | | Add Value of Dividends or other Earnings Paid on Stock or Option Awards not Otherwise Reflected in Fair Value or Total Compensation | $— | $— | $— | | Compensation Actually Paid | $7,315,842 | $2,928,935 | $11,214,092 |

  112. Adjustments to Determine Compensation Actually Paid

    1.We have not reported any amounts in our Summary Compensation Table with respect to “Change in Pension and Non-qualified Deferred Compensation” and, accordingly, the adjustments with respect to such items prescribed by the pay-versus-performance rules are not relevant to our analysis and no adjustments have been made. 2.The amounts reflect the aggregate grant-date fair value reported in the “Stock Awards” and “Option Awards” columns in the Summary Compensation Table for the applicable year. 3.In accordance with Item 402(v) requirements, the fair values of unvested and outstanding equity awards to our CEO were remeasured as of the end of each fiscal year, and as of each vesting date, during the years displayed in the table above. We approached the determination of fair value in the same way as we historically have determined fair value and fair values as of each measurement date were determined using valuation assumptions and methodologies (including expected term, volatility, dividend yield, and risk-free interest rates) that are generally consistent with those used to estimate fair value at grant under US GAAP. The average compensation actually paid to our non-CEO NEOs for the relevant fiscal year, as determined under SEC rules (and described below), includes the individuals indicated in the table below for each fiscal year:

  113. Adjustments to Determine Compensation Actually Paid

    | 2021 | 2022 | 2023 | | Jeff Cooper | Jeff Cooper | Jeff Cooper | | Priscilla Hung | Priscilla Hung | Priscilla Hung | | Winston King | Winston King | Winston King | | Frank O’Dowd | John Mullen | John Mullen | | | Frank O’Dowd | |

  114. Adjustments to Determine Compensation Actually Paid

    | Guidewire Software, Inc. | 66 | 2023 Proxy Statement |

  115. Adjustments to Determine Compensation Actually Paid

    Average compensation actually paid to our non-CEO NEOs represents the “Total” compensation reported in the Summary Compensation Table for the applicable fiscal year, as adjusted as follows:

  116. Adjustments to Determine Compensation Actually Paid

    | | 2021 | 2022 | 2023 | | Summary Compensation Table Total for non-CEO NEOs(1) | $3,007,199 | $6,354,350 | $3,940,333 | | Subtract Grant Date Fair Value of Option Awards and Stock Awards Granted in Fiscal Year(2) | $(2,274,596) | $(5,568,306) | $(3,061,945) | | Add Fair Value at Fiscal Year-End of Outstanding and Unvested Option Awards and Stock Awards Granted in Fiscal Year(3) | $2,167,180 | $3,235,840 | $3,571,601 | | Adjust for Change in Fair Value of Outstanding and Unvested Option Awards and Stock Awards Granted in Prior Fiscal Years(3) | $(228,438) | $(594,349) | $251,249 | | Adjust for Fair Value at Vesting of Option Awards and Stock Awards Granted in Fiscal Year That Vested During Fiscal Year(3) | $219,589 | $342,075 | $310,205 | | Adjust for Change in Fair Value as of Vesting Date of Option Awards and Stock Awards Granted in Prior Fiscal Years For Which Applicable Vesting Conditions Were Satisfied During Fiscal Year(3) | $(80,159) | $(104,446) | $(151,890) | | Subtract Fair Value as of Prior Fiscal Year-End of Option Awards and Stock Awards Granted in Prior Fiscal Years That Failed to Meet Applicable Vesting Conditions During Fiscal Year(3) | $— | $(572,308) | $— | | Add Value of Dividends or other Earnings Paid on Stock or Option Awards not Otherwise Reflected in Fair Value or Total Compensation | $— | $— | $— | | Compensation Actually Paid | $2,810,775 | $3,092,856 | $4,859,553 |

  117. Adjustments to Determine Compensation Actually Paid

    1.We have not reported any amounts in our Summary Compensation Table with respect to “Change in Pension and Non-qualified Deferred Compensation” and, accordingly, the adjustments with respect to such items prescribed by the pay-versus-performance rules are not relevant to our analysis and no adjustments have been made. 2.The amounts reflect the aggregate grant-date fair value reported in the “Stock Awards” and “Option Awards” columns in the Summary Compensation Table for the applicable year. 3.In accordance with Item 402(v) requirements, the fair values of unvested and outstanding equity awards to our non-CEO NEOs were remeasured as of the end of each fiscal year, and as of each vesting date, during the years displayed in the table above. We approached the determination of fair value in the same way as we historically have determined fair value and fair values as of each measurement date were determined using valuation assumptions and methodologies (including expected term, volatility, dividend yield, and risk-free interest rates) that are generally consistent with those used to estimate fair value at grant under US GAAP.

  118. Adjustments to Determine Compensation Actually Paid

    | Guidewire Software, Inc. | 67 | 2023 Proxy Statement |

  119. Pay Versus Performance Measures

    Pay Versus Performance Measures We believe the following performance measures represent the most important measures used by us to link compensation actually paid to the performance of our NEOs for the fiscal year ended July 31, 2023: •Annual Recurring Revenue (70% Weighting); •Adjusted Non-GAAP Operating Profit (25% Weighting); and •NPS/ESG Performance (5% Weighting). For additional details regarding our important performance measures, please see the sections entitled “Compensation Program Design” and “Executive Compensation Program Elements” in our Compensation Discussion and Analysis as set forth above in this Proxy Statement.

  120. Pay Versus Performance Measures

    | Guidewire Software, Inc. | 69 | 2023 Proxy Statement |