DEF 14A of Hamilton Insurance Group, Ltd., Mar 24, 2026

DEF 14A of Hamilton Insurance Group, Ltd.

Filed Mar 24, 2026 · FY20250001593275-26-000037

Open on EDGAR

  1. Class B Director Nominees

    Class B Director Nominees The Nominating and Corporate Governance Committee has recommended, and our Board has approved, David A. Brown, Giuseppina (Pina) Albo, John J. Gauthier, Karen Ann Green, Anu (Henna) Karna, Neil Patterson, Marvin Pestcoe, David Priebe, Everard Barclay Simmons, Therese Vaughan and Peter W. Wilson as Class B director nominees for election as directors at the Annual General Meeting. If elected, each such nominee will serve as a director until the 2027 annual general meeting or until his or her successor is duly elected and qualified.

  2. Class B Director Nominees

    | Name | Age | Committees | Position | Since | | David A. Brown | 68 | Compensation and Personnel | Independent Director | 2013 | | Giuseppina (Pina) Albo | 63 | | CEO and Director | 2018 | | John J. Gauthier | 64 | Compensation and Personnel, Nominating and Governance and Investment | Independent Director | 2023 | | Karen Ann Green | 58 | Audit, Underwriting and Risk and Compensation and Personnel | Independent Director | 2025 | | Anu (Henna) Karna | 49 | Nominating and Governance and Technology | Independent Director | 2023 | | Neil Patterson | 62 | Audit, Nominating and Governance and Technology | Independent Director | 2024 | | Marvin Pestcoe | 65 | Underwriting and Risk, Investment and Technology | Independent Director | 2020 | | David Priebe | 67 | Audit, Underwriting and Risk and Technology | Independent Director | 2025 | | Everard Barclay Simmons | 53 | Audit, Investment and Technology | Independent Director | 2023 | | Therese Vaughan | 69 | Compensation and Personnel, Nominating and Governance and Underwriting and Risk | Independent Director | 2024 | | Peter W. Wilson | 66 | Proposed to be on Underwriting and Risk, Nominating and Governance and Technology | Independent Director | First-time Nominee |

  3. Class B Director Nominees

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 6 |

  4. Class B Director Nominee Biographies

    Class B Director Nominee Biographies

  5. Class B Director Nominee Biographies

    | David A. Brown | Mr. Brown has served as a director of the Company since 2013 and currently serves as Chair of the Board. He also has served as non-executive Chair of Hamilton Re, Ltd. since 2015. Mr. Brown previously served as the Chief Executive Officer at Flagstone Reinsurance Holdings Ltd. from September 2005 until its sale in November 2012. Mr. Brown was also the Chief Executive Officer of Centre Solutions from 1994 to 1997, and was a partner with Ernst & Young, Bermuda until 1993. In addition, Mr. Brown has extensive experience serving on the boards of various public and private companies, including currently serving on the boards of Miami International Holdings, Allshores Limited and Equitable Financial Bermuda Re Ltd. Mr. Brown is also a member of the Chartered Professional Accountants of Bermuda and a fellow of the Institute of Chartered Accountants in England and Wales. We believe Mr. Brown’s business and leadership experience in the reinsurance industry and his financial expertise qualify him to serve on the Company’s Board. |

  6. Class B Director Nominee Biographies

    | Giuseppina (Pina) Albo | Ms. Albo has served as Chief Executive Officer of the Company and a member of its Board since January 2018. Ms. Albo began her career as a lawyer in Toronto, Canada. After practicing in real estate, corporate finance and M&A, she accepted a position at Munich Re as a claims expert. During her 25-year career at Munich Re, Ms. Albo held increasingly senior positions which included Head of Casualty Unit, North America/UK and International D&O/EPL; Head of Casualty Operations at Munich Reinsurance Company of Canada and Temple Insurance Company; Executive Head of Department UK and Ireland; President, National Clients Division, Munich Re America; and President, Reinsurance Division, Munich Re America. Ms. Albo’s last position at Munich Re was Member of the Board of Executive Management where her responsibilities included P&C business and operations in Europe and Latin America. Ms. Albo currently sits on the Board of the Reinsurance Group of America, the Association of Bermuda Insurers and Reinsurers (Chair 2022-2024), and is an Advisor to Overalls. She has also served as an ambassador for the Insurance Supper Club, an international organisation that aims to improve networking opportunities for women across the finance and insurance industries. Ms. Albo has been a member of many industry boards including the Board of the Insurance Information Institute, the Board of the Reinsurance Association of America, and the National Board of the Insurance Industry Charitable Foundation. She has been recognized for her contributions to the insurance industry and has received numerous awards including the Association of Professional Insurance Women’s “Woman of the Year” (2011). She was designated a “Top Influencer” in Insurance Business America’s List of “Hot 100” (2014) and placed on Intelligent Insurer’s list of ‘Top 100 Women in Re/insurance” (2014 and 2015). Ms. Albo holds a Maîtrise en Droit, International and European Community Law, from L’Université d’Aix-Marseille III, Aix-en-Provence, France; a Juris Doctor from Osgoode Hall Law School, York University, Toronto, Canada; and a Bachelor of Arts degree in Languages from the University of Winnipeg, Winnipeg, Manitoba, Canada. We believe Ms. Albo’s extensive experience in the insurance industry and in leadership positions qualifies her to serve on the Company’s Board. |

  7. Class B Director Nominee Biographies

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 7 |

  8. Class B Director Nominee Biographies

    | John J. Gauthier | Mr. Gauthier has served as a director of the Company since October 2023. He served as President of Allied World Financial Services Company, Inc. from 2012 until his retirement in 2018 and as Chief Investment Officer of Allied World Assurance Company Holdings, AG. from 2008 to 2018. Before joining Allied World, Mr. Gauthier was a Managing Director with Goldman Sachs Asset Management and held positions of increasing responsibility with Conning Asset Management culminating in a position as Director of Investment Strategy for Conning’s property-casualty insurer clients. Prior to joining Conning Asset Management, Mr. Gauthier held positions at General Reinsurance/New England Asset Management and The Travelers. Mr. Gauthier holds a Bachelor of Science degree in Computer Information Systems from Quinnipiac College and a Master of Business Administration, Finance from The Wharton School of the University of Pennsylvania. He is a Principal at JJG Advisory, LLC, a consulting business, and at Talcott Capital Partners, LLC, an investor advisory business. Mr. Gauthier is a member of the boards of directors of Reinsurance Group of America, Incorporated where he chairs the Investment Committee, The Hartford Funds, and Middlesex (CT) Health Systems. Mr. Gauthier served on the Board of Crescent Acquisition Corporation from 2018-2021. We believe Mr. Gauthier’s extensive financial and business experience in leadership positions qualifies him to serve on the Company’s Board. |

  9. Class B Director Nominee Biographies

    | Karen Ann Green | Ms. Green has served as a director of the Company since 2025. She also serves as the Senior Independent Director for each of Standard Life Plc (previously Phoenix Group Holdings PLC), Great Portland Estates PLC and the Miller broking business (Miller Insurance Services LLP and Ben Nevis CleanCo Ltd). Ms. Green also serves as a Non-Executive Director for the TMF Group and the Admiral Insurance Group PLC (including as Chair of the Remuneration Committee) as well as an advisor to Cytora Ltd. She was previously a Council Member of Lloyd’s of London and a Non-Executive Director of Asta Managing Agency Ltd and Aspen Managing Agency Ltd. During her executive career, Ms. Green held various senior executive positions at Aspen Insurance Holdings including Chief Executive of Aspen UK, (comprising the UK insurance and reinsurance companies) and Group Head of Strategy and Corporate Development. Prior to this she worked as a principal with the global private equity firm MMC Capital Inc (now Stone Point Capital) having previously worked in business development at GE Capital in London. She was also previously Vice President of the Insurance Institute of London. She began her career as an investment banker with Baring Brothers and then Schroders. She is a Trustee of Wellbeing of Women as well as a Governor of Bute House Preparatory School for Girls Ltd. We believe that Ms. Green's extensive financial services experience and leadership experience qualify her to serve on the Company's Board. |

  10. Class B Director Nominee Biographies

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 8 |

  11. Class B Director Nominee Biographies

    | Anu (Henna) Karna | Dr. Karna has served as a director of the Company since October 2023. She has more than 25 years of experience leading innovation across digital/data in high-tech, CPG, risk management, and insurance industries. Dr. Karna has led businesses and advised Fortune 50 companies on digital innovation and disruption and has designed and developed patent-pending technology and applications in the field of genetic algorithms, behavioral analytics, deep neural nets and digital-data technologies. Currently, Dr. Karna is a co-founder and chief product & AI officer for NeuroVitals, a digital, healthtech company. Prior to that, Dr. Karna served as the General Manager, Managing Director, Global Insurance & Risk Management Solutions at Google from 2020 to 2023. Prior to Google, she served as Executive Vice President and Global Chief Data Officer at AXA XL from 2017 to 2020, as President of Verisk Digital Services, as Vice President, Digital Customer Strategy for Verisk Analytics and as Managing Director & Global Actuarial Chief Information Officer for AIG. Earlier in her career, Dr. Karna held positions at Affinnova, John Hancock Insurance and held cryptology-related roles for the government. Dr. Karna holds a Bachelor of Science from Worcester Polytechnic Institute, a Masters and Doctorate from the University of Massachusetts, Lowell and a Master of Business Administration from the Massachusetts Institute of Technology. She has a senior fellowship from Harvard University and is currently serving as an associate there, focusing on use of AI and social impact. She is a member of the board of directors of Essent Group Ltd, AAA NE, and The Doctors Company. We believe Dr. Karna’s extensive experience in the insurance and tech industries as well as in leadership positions qualifies her to serve on the Company’s Board. |

  12. Class B Director Nominee Biographies

    | Neil Patterson | Mr. Patterson has served as a director of the Company and as chair of our audit committee since March 2024. Mr. Patterson is the retired Chairman of the KPMG group of entities in Bermuda. He spent the majority of his career with KPMG, having joined the firm in 1989. He was a client facing lead audit partner from 1997 until his retirement on December 31, 2020; providing audit and advisory services to financial services clients in Bermuda. He was the Risk Management Partner for KPMG in Bermuda for over twenty years and was the Risk Management Partner for KPMG’s sub regional firm (The KPMG Islands Group) for fifteen years. Mr. Patterson became the Bermuda firm’s Office Managing Partner in 2008 and served for nine years, he then took on the role of Chairman until his retirement. From 2012 until 2015, Mr. Patterson served as the Managing Partner of The KPMG Islands Group. In this capacity, he was also a member of KPMG’s Board for its European, Middle East and Africa firm. From 2016 to 2020 Mr. Patterson served as a member of KPMG’s Global Insurance Advisory Group, a sub-committee of KPMG’s global board. The Group advises the KPMG global board on insurance matters affecting KPMG member firms around the world. Mr. Patterson is very active in the Bermuda community. In 2019 he co-founded Ignite Bermuda, the island’s first privately funded business incubator and accelerator. Ignite’s purpose is to help Bermudian entrepreneurs succeed in business, diversify economic ownership and create jobs through education, mentoring and support. To date over 500 Bermudian entrepreneurs and small businesses have benefited from the programme. In 2021, he co-founded Bermuda Investor Community Limited, which is designed to enhance the flow of capital from angel investors into the entrepreneurial community in Bermuda. It provides coaching and advisory services to entrepreneurs seeking capital and promotes an electronic platform where investors and entrepreneurs can enter into transactions. In January, 2026 Mr. Patterson was awarded the King’s Certificate and Badge of Honour by King Charles III for his services to the Bermuda community. We believe Mr. Patterson's extensive financial and audit experience qualifies him to serve on the Company’s Board. |

  13. Class B Director Nominee Biographies

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 9 |

  14. Class B Director Nominee Biographies

    | Marvin Pestcoe | Mr. Pestcoe has served as a director of the Company since 2020 and Chair of our Underwriting & Risk Committee since May 2023. He also currently serves as non-executive Chair of Hamilton Select Insurance LLC. Mr. Pestcoe served as Executive Chair and Chief Executive Officer of Langhorne Re from January 2019 to April 2021 and continued as a director of Langhorne Re until March 2023. He is also currently a director at Catalina Insurance and a director of Employer’s Insurance. Mr. Pestcoe previously held senior positions in PartnerRe (2001 to 2017) and Swiss Re New Markets (1997 to 2001), and has over 40 years of experience in insurance, reinsurance and investments including a range of executive roles and leadership positions that focused on profit center management, investments, corporate strategy, data analytics and risk management. Mr. Pestcoe is also a Fellow of the Casualty Actuarial Society and a member of the American Academy of Actuaries. We believe Mr. Pestcoe’s expertise in insurance, reinsurance, investing and business leadership experience qualify him to serve on the Company’s Board. |

  15. Class B Director Nominee Biographies

    | David Priebe | Mr. Priebe has served as a director of the Company since 2025. Mr. Priebe is a seasoned leader in the reinsurance industry with expertise in capital markets and investment banking and a career that spanned over four decades at Guy Carpenter and Company ("GC"). Mr. Priebe recently retired from GC in January 2025. Mr. Priebe held the role of Chairman, with an emphasis on advancing GC’s engagement with clients and markets to identify opportunities and deliver solutions that help them drive profitable growth. Mr. Priebe was responsible for GC Securities, GC’s investment banking and capital markets group and GC Capital Solutions Group, which focused on delivering solutions that assist companies achieve their growth, capital and profitability objectives. Prior to becoming Chairman, Mr. Priebe was also Vice Chairman and previously held various senior leadership roles at GC, including as Executive Vice President, CEO and President of the UK and Continental Europe operations, Managing Director – Global Leaders of the Center of Excellence Practice Group, Managing Director – Global Leader of the Property Specialty Group and Managing Director – Client Account Executive. Mr. Priebe holds a Bachelor of Arts degree in Economics from St. Lawrence University as well as AICPCU/Wharton Advanced Executive Education. We believe Mr. Priebe’s extensive insurance industry experience qualifies him to serve on the Company’s Board. |

  16. Class B Director Nominee Biographies

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 10 |

  17. Class B Director Nominee Biographies

    | Everard Barclay Simmons | Mr. Simmons has served as a director of the Company since August 2023. Mr. Simmons is Chair and CEO at advisory firm Rose Investment Limited and Chair of the Bermuda Public Funds Investment Committee with responsibility for advising on the investment of Bermuda’s pension funds. He was formerly an investment banker with Goldman Sachs in New York and returned to Bermuda in 2006 as Managing Partner of Bermuda law firm Attride-Stirling & Woloniecki, where he worked until 2019. Mr. Simmons is a graduate of the University of Kent at Canterbury, where he graduated with a law degree, the Inns of Court School of Law where he qualified as a barrister, and Harvard Business School where he graduated with a Master in Business Administration. He is a member of the boards of Petershill Partners plc and Allshores Limited and is a former Chair of Butterfield Bank. We believe Mr. Simmons’ extensive financial and business experience in leadership positions qualifies him to serve on the Company’s Board. |

  18. Class B Director Nominee Biographies

    | Therese Vaughan | Ms. Vaughan has served as a director of the Company since March 2024. Ms. Vaughan is a seasoned educator, corporate director, and internationally recognized expert in insurance regulation. She was the CEO of the National Association of Insurance Commissioners and served over 10 years as Iowa Insurance Commissioner—the state’s longest-serving and first female insurance commissioner. Ms. Vaughan represented the US insurance regulatory system internationally, as a member of the Executive Committee of the International Association of Insurance Supervisors and of the steering committing for the US/EU Insurance Dialogue Project. She chaired the Joint Forum, a Basel, Switzerland-based group of banking, insurance, and securities supervisors. Ms. Vaughan recently served as a director of AIG, and is on the Board of Verisk Analytics, Wellmark Blue Cross and Blue Shield, WestBank, and the Food Bank of Iowa. We believe Ms. Vaughan’s extensive experience in insurance regulatory oversight and in leadership positions qualifies her to serve on the Company’s Board. |

  19. Class B Director Nominee Biographies

    | Peter W. Wilson | Mr. Wilson is being nominated for the first time as a potential director of the Company. Mr. Wilson is an accomplished insurance industry executive with more than three decades of leadership experience across global specialty, commercial, and professional liability markets. Most recently, he served as Chief Executive Officer of AXIS Insurance, where he led the company’s global Specialty Lines portfolio and oversaw operations across the U.S., U.K., Canada, Bermuda, Singapore, and Brussels. Under his leadership, AXIS Insurance grew gross written premiums from $2.4 billion to $4.9 billion, strengthened underwriting performance, integrated major acquisitions, and launched new digital distribution initiatives. Before joining AXIS, Mr. Wilson spent 20 years at CNA Insurance Companies, including as President and Chief Operating Officer of CNA Specialty. Mr. Wilson began his career at AIG, ultimately serving as Executive Vice President overseeing the commercial public Directors & Officers business. He served on multiple boards, including AXIS Specialty, Harrington Re , CNA Europe, CNA Surety and, most recently, QBE Insurance Group Board where he served on both the Audit and Risk Committees. He is a former President of the Professional Liability Underwriting Society (PLUS) and the PLUS Foundation. He holds a Bachelor of Arts in Economics and has completed advanced executive education programs. We believe Mr. Wilson’s extensive industry experience and executive leadership qualify him to serve on the Company's Board. |

  20. Class B Director Nominee Biographies

    | The Board recommends a vote "FOR" the election of the Class B Director nominees |

  21. Class B Director Nominee Biographies

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 11 |

  22. Board Composition

    Board Composition We believe it is essential to have a qualified group of directors with an appropriate mix of skills, experience and attributes to oversee our business. Accordingly, the size and composition of the Board are reviewed periodically to balance the need for diverse perspectives and expertise, with the practical considerations of efficient corporate governance. In addition to the foregoing, we entered into the Shareholders Agreement with certain shareholders who, together with their affiliates, owned at least 5% of our issued and outstanding common shares as of that date. Those shareholders included: the Magnitude Investor (collectively being, Magnitude Master Fund, a sub trust of the Magnitude Master Series Trust, Magnitude Institutional, Ltd., Magnitude Partners Master Fund, L.P., and Magnitude Insurance Master Fund, LLC), Sango Holdings (being Sango Hoken Holdings, LLC), Hopkins Holdings (being Hopkins Holdings, LLC) and the Blackstone Investor Group (collectively comprising BSOF Master Fund L.P. and BSOF Master Fund II L.P.), including any permitted transferee of any of the foregoing. Under the Shareholders Agreement, each such shareholder had the right to appoint one Shareholder Director, subject to the maintenance of certain ownership thresholds. Following the sale of its holdings in Hamilton back to the Company in 2024, the Blackstone Investor Group no longer meets the ownership threshold and its appointment right has terminated. The remaining Class B directors are elected by the holders of our Class B common shares for an annual term expiring at each annual general meeting or until their successors are elected or appointed or their office is otherwise vacated. Currently, the Shareholder Directors are Bradley Cooper and Marc Roston (who succeeded H. Hawes Bostic III as the Magnitude Investor director in February 2026) and the Class B directors are David A. Brown, Giuseppina (Pina) Albo, John J. Gauthier, Karen Ann Green, Anu (Henna) Karna, Stephen W. Pacala, David Priebe, Neil Patterson, Marvin Pestcoe, Everard Barclay Simmons and Therese Vaughan. Sango Holdings has retained its right to appoint one director pursuant to the terms of the Shareholders Agreement, but this seat currently remains unfilled. In addition to the two (2) Shareholder Directors appointed in accordance with the Shareholders Agreement, the Board has nominated eleven (11) individuals to serve as Class B directors based upon the recommendation of the Nominating and Corporate Governance Committee. Ten of these individuals are incumbent directors and were elected by the shareholders at our 2025 annual general meeting. The other remaining individual, Peter W. Wilson, is being nominated for the first time as a potential director based upon the recommendation of the Nominating and Corporate Governance Committee following a comprehensive search and review of suitable candidates. This process incorporated the valuable referrals of industry contacts of our executive officers, which played a crucial role in identifying this qualified candidate. Our bye-laws provide that our Board may appoint such officers as it may determine. This provides the Board with the flexibility to combine or separate the positions of Chairperson of the Board and Chief Executive Officer should it determine that utilizing one or the other structure would be in the best interests of the Company. David A. Brown, a non-executive director, continues to serve as Chairperson of the Board. Our Board has concluded that our current leadership structure is appropriate at this time in light of the Board’s size and the cooperative and dynamic working relationship among our directors, including the Shareholder Directors and independent directors. However, our Board will continue to periodically review our leadership structure and may make such changes in the future as it deems appropriate.

  23. Board Composition

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 12 |

  24. Shareholder Directors

    Shareholder Directors Set forth below, and not for nomination or election at the Annual General Meeting, are the biographies of the two current Shareholder Directors:

  25. Shareholder Directors

    | Bradley Cooper | Mr. Cooper, age 59, has served as a director of the Company since 2024. Mr. Cooper is a Managing Partner of Capital Z Partners, a private equity fund focused on investing in the financial services sector. Prior to founding Capital Z in 1990, Mr. Cooper was an investment banker in the Financial Institutions Group of Salomon Brothers (now Citigroup). He has extensive Board experience with both publicly traded and privately held companies, having served on, and chaired many committees. Mr. Cooper served on the Board of non-profit Make-A-Wish Foundation of Metro New York for 16 years, the final three as Chair, and the University of Michigan, Stephen M. Ross School of Business Advisory Board for approximately 8 years. We believe that Mr. Cooper’s extensive experience in the financial services sector and business leadership experience qualify him to serve on the Company’s Board. Mr. Cooper was appointed as a director of the Company pursuant to Hopkins Holdings, LLC’s right under the Shareholders Agreement to appoint a director to the Board. | | Marc Roston | Mr. Roston, age 56, has served as a director of the Company since February 2026. Mr. Roston is a Senior Research Scholar at Stanford University, where he has been affiliated since 2020. He also serves as an Operating Partner of DFW Capital Partners, a private equity firm, a role he has held since 2020, and has advised hedge funds, private equity firms, insurance companies, and family offices since 2009 through his advisory and investment firm, MNR Capital LLC. Mr. Roston has more than 30 years of experience as an investment professional, with extensive experience analyzing and evaluating financial performance and business strategy across a wide range of companies. Mr. Roston has served on the boards of several privately held companies, including Vantage Insurance Partners from September 2020 through January 2025 and ResourcePro Holdings LLC from September 2020 through December 2021. Mr. Roston holds a Ph.D. in Economics from the University of Chicago and a B.S. in Economics from Carnegie Mellon University. We believe that Mr. Roston’s extensive investment experience, analytical expertise, and knowledge of financial and economic matters qualify him to serve on the Company’s Board. Mr. Roston was appointed as a director of the Company pursuant to Magnitude Capital’s right under the Shareholders Agreement to appoint a director to the Board. |

  26. Consideration of Director Nominees

    Consideration of Director Nominees The Nominating and Corporate Governance Committee will consider candidates recommended by shareholders to be nominated to our Board for election at the Annual General Meeting. A shareholder who wishes to submit a candidate for consideration must be a shareholder of record at the time that such shareholder submits a candidate for nomination and must be entitled to vote for the candidate at the meeting. If the shareholder (or a qualified representative of the shareholder) does not appear at the Annual General Meeting to present a nomination or other proposed business, such nomination shall be disregarded or such proposed business shall not be transacted, as the case may be, notwithstanding that proxies in respect of such vote may have been received by the Company. Shareholders who wish to submit director nominees for election at the 2027 annual general meeting of shareholders must follow the notice procedures described in “Shareholder Proposals for the 2027 Annual General Meeting." The notice must include: •The name and address of such shareholder (as they appear in the Company's Register of Members) and any such beneficial owner •The class or series and number of shares of the Company which are held of record or are beneficially owned by such shareholder and by any such beneficial owner •A description of any agreement, arrangement or understanding between or among such shareholder and any such beneficial owner, any of their respective affiliates or associates, and any other person or persons (including their names) in connection with the proposal of such nomination or other business

  27. Consideration of Director Nominees

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 23 |

  28. Consideration of Director Nominees

    •A representation that the shareholder is a holder of record of shares of the Company entitled to vote at such general meeting and that that shareholder (or qualified representative of that shareholder) intends to appear in person or by proxy at the general meeting to bring such nomination or other business before the general meeting •A representation as to whether such shareholder or any such beneficial owner intends or is part of a group that intends to (i) deliver a proxy statement and/or form of proxy to holders of at least the percentage of the voting power of the Company’s outstanding shares required to approve or adopt the proposal or to elect each such nominee and/or (ii) otherwise to solicit proxies from shareholder in support of such proposal or nomination. A shareholder shall also comply with all applicable requirements of the Exchange Act.

  29. Compensation Philosophy — Section II

    Compensation Philosophy — Section II Our compensation philosophy is performance-driven and designed to align the financial interests of our executive officers, including our NEOs, with those of our shareholders. The key principles of our approach are: Attract, motivate, and retain: We seek leaders with diverse experience, expertise, and perspectives to execute our strategy and deliver profitable growth. In setting competitive pay levels, we reference compensation practices and structures within our peer group. Emphasize pay-for-performance through significant variable compensation: A substantial portion of executive pay is variable and at risk, reflecting Company performance and the executives’ ability to influence enterprise-wide results. Variable components include annual cash incentives and long-term equity awards, which are directly tied to financial, strategic, and business goals. This structure reinforces a pay-for-performance culture and provides upside potential for exceeding targets. Reward achievement of clear, measurable objectives within a market context: Our program incentivizes executives to achieve goals that advance strategic and business objectives and increase shareholder value by linking Company and individual performance to compensation. We set clear, measurable quantitative and qualitative goals designed to elevate results and returns to shareholders. We strive for our rewards to be market competitive, aligned with market practice, and considerate of shareholder interests. Align executive interests with shareholders through equity and long-term incentives: Equity-based long-term incentive compensation constitutes a significant portion of our executive officers’ overall compensation. We use equity as the form for long-term incentives to motivate and reward executive officers to achieve multi-year strategic goals and deliver sustained long-term value to shareholders. Equity compensation creates strong alignment with shareholders, provides a common interest in share price performance and fosters an ownership culture among executive officers by making them shareholders with a personal stake in the value they help to create. Reward talent through a fair, competitive, and reasonable process: We believe that our executive compensation program should incentivize our executive officers to achieve our business goals and enable us to attract and retain executives whose talents, expertise, leadership, and contributions build and sustain growth in long-term shareholder value. To achieve these objectives, we regularly review our compensation policies and overall program design to ensure they are aligned with the interests of our shareholders and our business goals, and that the total compensation paid to our executives is fair, reasonable, and competitive for our size and stage of development.

  30. Compensation Program Governance — Section III

    | No Guaranteed Performance Bonuses | We do not provide guaranteed performance bonuses to our NEOs at any minimum levels of payment under our annual cash incentive plan | | No Dividend Equivalents on Unvested Performance Awards | We do not pay dividends or dividend equivalents on performance-based awards unless and until the performance awards are earned and vested |

  31. Annual Incentive Opportunity

    Annual Incentive Opportunity Our Compensation and Personnel Committee used Company financial and strategic and operational performance goals for the Company's annual cash incentive program. Our Compensation and Personnel Committee worked closely with management and with guidance from its independent compensation consultant to establish the targets and goals for the annual cash incentive program, setting them at levels that it considered rigorous and challenging, requiring substantial effort to achieve, appropriately incentivizing performance and considering the relevant risks and opportunities. a.Financial Goals. 60% of the amount of the annual incentive pool funding was based on underwriting profitability as measured by our combined ratio (as described below). The Compensation and Personnel Committee selected this measure because it focuses executives on this critical business priority. b.Strategic and Operational Goals. 40% of the amount of the annual incentive pool funding was based on the following strategic and operational measures: 1. Strategic Growth (20%) – actions to sharpen our strategic focus, align our organizational structure with the group strategy and focus execution in line with communicated priorities to grow in the right lines of business at the right time in the cycle while continuing to optimize portfolio composition. 2. Technology Enablement (10%) – actions to enhance technology capabilities, continue to build facilitating business platforms, capture data, and improve analytics. 3. Magnet for Talent (10%) – actions to attract, develop and retain talent within the organization and create a vibrant entrepreneurial culture that fosters communication, collaboration and alignment with our corporate values and the execution of our sustainability strategy. 1.This range excludes incremental increases provided to Messrs. Daws and Baker in connection with their respective appointments to new roles during the year

  32. Annual Incentive Opportunity

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 43 |

  33. Annual Incentive Opportunity

    For the financial goal (60%), the combined ratio for the fiscal year ended December 31, 2025 was 92.9%. This performance equates to 182.3% of target achievement which translates to 109.4% earnings on the financial portion. For the strategic and operational goals (40%), the Compensation and Personnel Committee determined that strategic growth (20%) was achieved at 150% of target, technology enablement (10%) was achieved at 100% and magnet for talent (10%) was achieved at 150%. These results translated to 55% earnings on the strategic and operational portion, for a total, when combined with the financial portion, of 164.4%. See “Compensation Program Components” below for more details on the types of strategic and operational goals.

  34. 2025 Long-Term Incentives

    2025 Long-Term Incentives Equity grants for our NEOs in the fiscal year ended December 31, 2025 consisted of performance-based vesting restricted stock units (“PSUs”) and time-based vesting restricted stock units (“RSUs”), with the target value divided evenly between these awards. Long-term incentive equity awards are prospective in nature and are intended to tie a substantial portion of an executive’s pay to creating long-term shareholder value. The Compensation and Personnel Committee structures the long-term incentive opportunity to motivate executive officers, including our NEOs, to achieve multi-year strategic goals and deliver sustained long-term value to shareholders, and to reward them for doing so. For the fiscal year ended December 31, 2025, the Compensation and Personnel Committee selected two equally weighted PSU performance metrics for the 2025-2027 PSU performance period: Return on Equity ("ROE") and Book Value per Share Growth ("BVSG"), each measured on an absolute basis over a three-year performance period. The 2025 metrics were the same as ones used in 2024. Performance achievement for the 2023-2025 PSU performance period was attained at 200% of target based on the achievement of three-year performance for underwriting return on capital.

  35. 2025 COMPONENTS IN GENERAL

    2025 COMPONENTS IN GENERAL The Compensation and Personnel Committee selected the components of compensation set forth in the chart below to achieve our executive compensation program objectives. The Compensation and Personnel Committee regularly reviews all components of the program to verify that each executive officer’s total compensation is consistent with our compensation philosophy and objectives, and that the component is serving a purpose in supporting the execution of our strategy. The majority of each executive officer’s compensation is variable and at-risk, with a meaningful portion that is performance based. Long-term incentive equity awards are prospective in nature and intended to tie a substantial portion of an executive’s pay to creating long-term shareholder value. In the fiscal year ended December 31, 2025, the Compensation and Personnel Committee structured the long-term incentive opportunity with PSUs and RSUs to motivate executive officers to achieve multi-year strategic goals and deliver sustained long-term value to shareholders and to reward them for doing so.

  36. 2025 COMPONENTS IN GENERAL

    | Element | Description | Additional Detail | | Base Salary | Fixed cash compensation based on each executive officer’s role, individual skills, experience, performance, and competitive market conditions | Intended to provide stable compensation to executive officers, allow us to attract and retain skilled executive talent and maintain a stable leadership team | | Short-Term Incentives: Annual Cash Incentive Opportunities | ◦Pool is 60% based on financial objectives and 40% based on strategic and operational goals ◦Variable cash compensation based on the level of achievement of pre-determined annual corporate and individual goals ◦Capped at a maximum of 200% of each NEO’s target opportunity | Designed to ensure executive officers are motivated to achieve our annual goals and reward them for doing so, and to attract and retain executive officers | | Long-Term Incentives: Annual Equity-Based Compensation | Variable equity-based compensation: ◦PSUs: Performance stock units that vest based on achievement of financial performance goals. ◦RSUs: Restricted stock units that vest based on the passage of time | Designed to motivate and reward executive officers to achieve our multi-year strategic goals and to deliver sustained long-term value to Shareholders, as well as to attract and retain executive officers. Links with shareholder value creation to align with shareholders’ interests |

  37. 2025 TARGET PAY MIX

    2025 TARGET PAY MIX Consistent with the Compensation and Personnel Committee’s pay-for-performance philosophy, a meaningful majority of annual target total compensation is variable, at-risk pay. The Compensation and Personnel Committee considers compensation to be “at-risk” if it is subject to operating performance or if its value depends on our share price. The following graphic shows the allocation of annual target total compensation payable to the Chief Executive Officer and the average allocation to the other NEOs. The Compensation and Personnel Committee allocated compensation among base salary, target annual cash incentive plan amounts and the grant date fair value of long-term incentives in the form of PSUs and RSUs. The values and allocations were determined by the Compensation and Personnel Committee with reference to, and consistent with, the allocations among such elements at the companies in our compensation peer groups.

  38. ANNUAL CASH INCENTIVE PLAN

    ANNUAL CASH INCENTIVE PLAN The annual cash incentive plan for executive officers is a cash-based plan that rewards executive officers, including our NEOs, for the achievement of key annual objectives. The structure of the annual cash plan incentivizes NEOs to meet or exceed annual financial and strategic and operational objectives and promotes collaboration through the achievement of common Company goals that the Compensation and Personnel Committee views as critical to the execution of our business strategy. There is a bonus pool under the annual cash incentive plan that is funded based on our achievement against the financial measure of profitability (weighted 60%) as measured by our combined ratio and the measures of strategic growth (weighted 20%), technology enablement (weighted 10%) and being a magnet for talent (weighted 10%), as more specifically described above and below. If achievement relative to these measures does not reach at least the threshold level, then the bonus pool as it relates to that achievement measure will not be funded, regardless of the NEO's individual performance. To the extent that the bonus pool is funded, the NEOs are entitled to payouts under the annual cash incentive plan based on the level of achievement relative to the financial and strategic and operational measures, subject to the Compensation and Personnel Committee’s discretion to decrease or increase the overall funding percentage and/or to decrease or increase any individual bonus payout.

  39. TARGET OPPORTUNITIES

    | NEO | 2024 Target Cash Incentive Opportunity (as a % of Base Salary) | 2025 Target Cash Incentive Opportunity (as a % of Base Salary) | | Giuseppina (Pina) Albo | 160 | 160 | | Craig Howie | 150 | 150 | | Adrian Daws | 140 | 140 | | Gemma Carreiro | 100 | 110 | | Alex Baker (1) | 110 | 120 | | Megan Graves | 140 | 140 |

  40. FINANCIAL MEASURE (60%)

    FINANCIAL MEASURE (60%) For the fiscal year ended December 31, 2025, 60% of the amount of the bonus pool funding for our annual cash incentive plan was based on underwriting profitability as measured by our combined ratio (as described below). The Compensation and Personnel Committee selected this measure because it focuses our NEOs and other executive officers on this critical business priority. We use the combined ratio as our measure of underwriting profitability. This ratio is a relative measurement that describes, for every $100 of net premiums earned, the amount of losses and loss adjustment expenses, and the amount of other underwriting expenses, that would be taken from the premium. A combined ratio of less than 100% indicates that the insurance company’s underwriting activities are profitable and a combined ratio of over 100% indicates an underwriting loss. The appropriate combined ratio target for a company depends upon its mix of business, as the underwriting environment varies across countries and products, as does the degree of litigation activity, all of which affect the combined ratio. In addition, investment returns, local taxes, cost of capital, regulation, product type and competition can affect pricing and consequently profitability, as reflected in underwriting income and associated ratios. For the financial measure, the Compensation and Personnel Committee set the target for combined ratio at a level that it considered rigorous and challenging, reflecting the Company’s risk profile and market conditions, and designed to require strong underwriting performance while maintaining appropriate underwriting discipline. The Committee believes this level appropriately balances the need to incentivize profitable growth with prudent risk management, thereby aligning executive actions with long-term shareholder value creation. In particular, the Compensation and Personnel Committee reviewed our annual operating budget for the fiscal year ended December 31, 2025 that resulted from our detailed budgeting process and evaluated various factors that might affect whether the target could be achieved, including the risks to achieving certain preliminary objectives that were necessary prerequisites to achieving the budget targets. Considering these factors, the Compensation and Personnel Committee set the target for combined ratio at 99.6% for the fiscal year ended December 31, 2025 and set the threshold level of performance at 118.4%, and the maximum level of performance at 91.0%, a level that required exceptionally strong performance and represented a significant challenge.

  41. STRATEGIC AND OPERATIONAL MEASURES (40%)

    STRATEGIC AND OPERATIONAL MEASURES (40%) For the fiscal year ended December 31, 2025, 40% of the amount of the bonus pool funding for our annual cash incentive plan is based on the following strategic and operational measures: •Strategic Growth (20%) – actions to sharpen our strategic focus, align our organizational structure with the refined strategy and focus execution in line with communicated priorities to grow in the right lines of business at the right time in the cycle while continuing to optimize portfolio composition •Technology Enablement (10%) – actions to enhance technology capabilities and service delivery, continue to build facilitating business platforms, capture data and improve analytics, and review and update the strategy •Magnet for Talent (10%) – actions to enhance internal and external communications, marketing strategy, desired culture, increased engagement and execution of our sustainability strategy. The Compensation and Personnel Committee believes that each of these goals is strongly aligned to the creation of shareholder value.

  42. ANNUAL CASH INCENTIVE POOL FUNDING

    ANNUAL CASH INCENTIVE POOL FUNDING The Compensation and Personnel Committee determined the annual cash incentive pool funding level based on the level of actual performance relative to the goals. To motivate performance and underscore the

  43. ANNUAL CASH INCENTIVE POOL FUNDING

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  44. ANNUAL CASH INCENTIVE POOL FUNDING

    importance of achieving, or closely approaching, the financial measure goal at this critical time in our development, the Compensation and Personnel Committee set the funding level at 0% for achievement below the threshold level of performance. For performance between the threshold level and the target level, the funding level increases from 0% for achieving threshold performance to 100% of the target opportunity for achieving target performance. For performance between the target level and the maximum level, the funding level ranges from 100% of the target opportunity to 200% of the target opportunity. Achievement above the maximum level is capped at the maximum funding level of 200% of target. For performance between the threshold and target and between target and maximum, the bonus funding level is determined by linear interpolation. For the strategic and operational measures, the Compensation and Personnel Committee similarly determines achievement relative to each measure based on its qualitative rating of where performance fell on a scale of “does not meet” to “exceed” and translates that performance level to a corresponding bonus funding level ranging from 0% to 200%.

  45. 2025 ACHIEVEMENT OF FINANCIAL AND STRATEGIC AND OPERATIONAL MEASURES

    | Performance Measures | Weighting (%) | Threshold (%) | Target (%) | Maximum (%) | Actual Result (%) | Performance Achievement (%) | Weighted Payout (%) | | Financial Measure: Combined Ratio | 60 | 118.4 | 99.6 | 91.0 | 92.9 | 182.3 | 109.4 | | Funding Percentage (as a % of target funding) | | 0 | 100 | 200 | | | | | Strategic and Operational Measures: | | | | | | | | | Strategic Growth | 20 | — | — | — | — | 150 | 30 | | Technology Enablement | 10 | — | — | — | — | 100 | 10 | | Magnet for Talent | 10 | — | — | — | — | 150 | 15 | | Aggregate Weighted Funding Percentage: | | | | | | | 164.4 |

  46. PAYOUT DETERMINATIONS

    PAYOUT DETERMINATIONS As described above, the Compensation and Personnel Committee verifies achievement relative to the target for the financial measure and the strategic and operational measures to determine the respective performance levels. The Compensation and Personnel Committee then adds the amounts for the two components together to determine the annual cash incentive pool funding. The Compensation and Personnel Committee then takes this bonus pool funding level, together with each NEO’s individual annual performance review, and determines the payout, which may be more or less than the NEO’s target, ranging from a minimum of 0% and up to a maximum (assuming 100% funding of the bonus pool) of 200%. Each NEO’s individual performance level, other than the CEO’s, is determined as recommended by the CEO to the

  47. PAYOUT DETERMINATIONS

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  48. PAYOUT DETERMINATIONS

    Compensation and Personnel Committee. The CEO’s individual performance level is determined by the Compensation and Personnel Committee based on its assessment of the achievement of Company goals. The total payout under our annual cash incentive plan for each NEO for the fiscal year ended December 31, 2025 is reflected in the following table:

  49. PAYOUT DETERMINATIONS

    | NEO | 2025 Base Salary ($) | 2025 Target Cash Incentive Opportunity (as a % of Base Salary) | Target Incentive ($) | Bonus Pool Funding Plus Individual Performance (%) | Total 2025 Cash Incentive Payout Amount ($) | | Giuseppina (Pina) Albo | 1,300,000 | 160 | 2,080,000 | 175 | 3,640,000 | | Craig Howie | 660,000 | 150 | 990,000 | 175 | 1,732,500 | | Adrian Daws (1) | 660,000 | 140 | 795,760 | 150(5) | 1,379,728 | | Gemma Carreiro (2) | 480,000 | 110 | 528,000 | 175 | 924,000 | | Alex Baker (3) | 509,200 | 120 | 547,614 | 150(6) | 920,761 | | Megan Graves (2)(4) | 650,000 | 140 | 910,000 | 165 | 1,501,500 |

  50. PAYOUT DETERMINATIONS

    1. The 2025 base salary for Mr. Daws is based on salary effective September 1, 2025 and paid in U.S. dollars. The target and total cash incentive payout amounts for the fiscal year ended December 31, 2025, were pro-rated based on his salary as of April 1, 2025, converted using the exchange rate on February 24, 2026, the date when the Compensation and Personnel Committee approved the payout, and his salary effective September 1, 2025. For Mr. Daws’ base salary effective April 1, 2025, the 2025 average exchange rate of $1.3400 was used. 2. All amounts paid to Ms. Carreiro and Ms. Graves were paid in Bermuda dollars (BMD). BMD is converted to the U.S. dollars using an exchange rate of 1:1. 3. All amounts paid to Mr. Baker were paid in British pound sterling. The 2025 base salary is based on salary effective September 1, 2025. The target and total cash incentive payout amounts for the fiscal year ended December 31, 2025, were converted to U.S. dollars using the exchange rate on February 24, 2026, the date when the Compensation and Personnel Committee approved the payout. For Mr. Baker’s base salary, the 2025 average exchange rate of $1.3400 per British pound sterling was used. 4. Ms. Graves retired as of December 31,2025. Per her Retirement Agreement (dated as of June 16, 2025) she remains eligible for her 2025 annual cash incentive plan payment at no less than target, payable in March 2026. 5. Mr. Daws was appointed CEO of Hamilton Re effective September 1, 2025. Prior to that date, he served as CEO of Hamilton Global Specialty. His 2025 annual bonus reflected a weighted‑average of the bonus funding levels applicable to each role, resulting in an overall payout of 150%. 6. Mr. Baker was appointed CEO of Hamilton Global Specialty effective September 1, 2025. Prior to that date, he served as Group Chief Risk Officer. His 2025 annual bonus reflected a weighted‑average of the bonus funding levels applicable to each role, resulting in an overall payout of 150%.

  51. LONG-TERM INCENTIVES

    LONG-TERM INCENTIVES The largest component of the executive compensation program is long-term incentive equity grants, which are prospective in nature and intended to tie a substantial portion of our NEOs' and other executive officers' pay to creating long-term shareholder value. The Compensation and Personnel Committee designed the long-term incentive opportunity to motivate and reward executive officers to achieve multi-year strategic goals and to deliver sustained long-term value to shareholders. The long-term incentives create a strong link between payouts and performance, and significant alignment between the interests of executive officers and the interests of our shareholders. Long-term equity incentives also promote retention because executive officers will receive value through the vesting schedule only if they remain employed by us over the required term. Equity incentives also foster an ownership culture among our executive officers by making them shareholders with a personal stake in the value they are intended to create. The Compensation and Personnel Committee chose to award PSUs because they reward NEOs for future performance if performance goals relating to sustained underlying value are achieved and RSUs because they provide a retentive vehicle and alignment with long-term business performance.

  52. LONG-TERM INCENTIVES

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  53. LONG-TERM INCENTIVE TARGET OPPORTUNITIES

    LONG-TERM INCENTIVE TARGET OPPORTUNITIES The employment agreements with each of our NEOs set forth annual targets for grants of PSUs and RSUs. The target levels are expressed as dollar amounts, equal to a certain percentage of the NEO’s base annual salary. The number of shares covered by the awards is determined by dividing the applicable target dollar amount by the per share fair market value of our shares as of the date of the fourth quarter Compensation Committee meeting on February 26, 2025 ($18.41) for the grants made during the fiscal year ended December 31, 2025). In February 2025, the Compensation and Personnel Committee authorized grants of awards to our NEOs under our 2023 Equity Incentive Plan at their respective annual grant targets. In affirming and establishing these grant levels, the Compensation and Personnel Committee considered the following: •The values of, allocations to, and proportion of total compensation represented by the long-term incentive opportunities at the companies in our compensation peer sets; •Individual performance, criticality, and expected future contributions of the NEO; •Time in role, skills, and experience; and •Retention The Compensation and Personnel Committee determines a target long-term incentive opportunity for each NEO under the long-term incentive plan by taking the individual’s base salary and multiplying it by the individual’s target incentive percentage. The Compensation and Personnel Committee also modified the target incentive percentages for the fiscal year ended December 31, 2025 to better align each NEO’s incentive targets to the market as follows:

  54. LONG-TERM INCENTIVE TARGET OPPORTUNITIES

    | NEO | 2024 Target Long-term Incentive Opportunity (as a % of Base Salary) | 2025 Target Long-term Incentive Opportunity (as a % of Base Salary) | | Giuseppina (Pina) Albo | 275 | 300 | | Craig Howie | 230 | 240 | | Adrian Daws | 160 | 170 | | Gemma Carreiro | 100 | 120 | | Alex Baker(1) | 120 | 120 | | Megan Graves | 160 | 170 |

  55. LONG-TERM INCENTIVE TARGET OPPORTUNITIES

    1. Following Mr. Baker’s appointment to CEO, Hamilton Global Specialty effective September 1, 2025, his long-term incentive target percentage was increased from 120% to 150% for his 2026 award.

  56. LONG-TERM INCENTIVE TARGET OPPORTUNITIES

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  57. EQUITY VEHICLES AND 2025 MIX: PSUs AND RSUs

    EQUITY VEHICLES AND 2025 MIX: PSUs AND RSUs The mix of long-term incentives granted to the NEOs during the fiscal year ended December 31, 2025 is shown in the following table:

  58. EQUITY VEHICLES AND 2025 MIX: PSUs AND RSUs

    | Equity Vehicle | 2025 Allocation | Vesting Period | Performance Metrics | Rationale for Use | | PSUs | 50% | 3-year cliff | •3-year average Return on Equity •3-year annualized Book Value per Share Growth | •Focuses on core profitability and sustainable growth •Prioritizes increasing shareholder value •Promotes long-term focus and retention | | RSUs | 50% | 3 years: 1/3 per year | •Value of stock at vesting | •Aligns with shareholders •Promotes retention •Provides value even during periods of share price or market underperformance |

  59. EQUITY VEHICLES AND 2025 MIX: PSUs AND RSUs

    The Compensation and Personnel Committee structured the mix of equity vehicles, and the relative weight assigned to each type of award to motivate performance against long-term goals through PSUs, and to ensure some amount of value delivery through the RSUs. These are complementary because they have upside potential but deliver some value even if the share price does not increase, while also reinforcing an ownership culture and commitment to us.

  60. PSU PERFORMANCE METRIC

    PSU PERFORMANCE METRIC For the fiscal year ended December 31, 2025, the Compensation and Personnel Committee retained the same equally-weighted performance metrics used in the prior year: three-year average Return on Equity (ROE) and three-year annualized Book Value per Share Growth ("BVSG"). These metrics align with peer group market practices and our status as a public company. ROE was selected because it measures the Company’s ability to generate profits, leading to sustainable growth and alignment with shareholder interests. BVSG was selected because it reflects the underlying value of the Company’s assets minus its liabilities, providing a clear measure of financial health and encouraging a long-term focus on sustainable performance.

  61. 2025 GRANTS OF PSUs AND RSUs

    2025 GRANTS OF PSUs AND RSUs The following table summarizes the grants to our NEOs:

  62. 2025 GRANTS OF PSUs AND RSUs

    | NEO | 2024 Base Salary ($) | 2025 Target Long-Term Incentive Opportunity (as a % of Base Salary) | Target Long-Term Incentive Value ($) | PSUs ($) | PSUs (#) | RSUs ($) | RSUs (#) | | Giuseppina (Pina) Albo | 1,300,000 | 300 | 3,900,000 | 1,950,000 | 105,921 | 1,950,000 | 105,921 | | Craig Howie | 640,000 | 240 | 1,536,000 | 768,000 | 41,717 | 768,000 | 41,717 | | Adrian Daws (1) | 491,684 | 170 | 835,863 | 417,931 | 22,478 | 417,931 | 22,478 | | Gemma Carreiro | 430,000 | 120 | 516,000 | 258,000 | 14,015 | 258,000 | 14,015 | | Alex Baker (2) | 421,443 | 120 | 505,732 | 252,866 | 13,600 | 252,866 | 13,600 | | Megan Graves | 635,000 | 170 | 1,079,500 | 539,750 | 29,319 | 539,750 | 29,319 |

  63. 2025 GRANTS OF PSUs AND RSUs

    1. All amounts paid to Mr. Daws for purposes of calculating 2025 long-term incentive opportunities were paid in British pound sterling. For purposes of this CD&A, all amounts paid to Mr. Daws during 2024 and 2025 were converted to U.S. dollars using the 2024 and 2025 average exchange rate, $1.2771 and $1.3400, respectively, except where otherwise indicated. 2. All amounts paid to Mr. Baker for purposes of calculating 2025 long-term incentive opportunities were paid in British pound sterling. For purposes of this CD&A, all amounts paid to Mr. Baker during 2024 and 2025 were converted to U.S. dollars using the 2024 and 2025 average exchange rate, $1.2771 and $1.3400, respectively, except where otherwise indicated.

  64. 2023 PSUs WITH PERFORMANCE PERIOD COMPLETED AS OF FISCAL YEAR ENDED DECEMBER 31, 2025

    2023 PSUs WITH PERFORMANCE PERIOD COMPLETED AS OF FISCAL YEAR ENDED DECEMBER 31, 2025 In 2023, the Compensation and Personnel Committee granted PSUs with performance-based vesting requirements for the three-year performance period of 2023-2025 based on underwriting return on capital, which had the following performance curve:

  65. 2023 PSUs WITH PERFORMANCE PERIOD COMPLETED AS OF FISCAL YEAR ENDED DECEMBER 31, 2025

    | 2023 Performance Measure | Below Threshold (%) | Threshold (%) | Target (%) | Maximum (%) | Maximum or Above (%) | Actual (%) | | Underwriting Return on Capital | <(2.3) | (2.3) | 3 | 6.6 | >6.6 | 8.6 | | Payout Percentage of Target Shares | 0 | 0 | 100 | 200 | 200 | 200 |

  66. 2023 PSUs WITH PERFORMANCE PERIOD COMPLETED AS OF FISCAL YEAR ENDED DECEMBER 31, 2025

    The Compensation and Personnel Committee determined that the annualized underwriting return on capital for the 2023-2025 period was 8.6%, and correspondingly approved a performance payout at 200% of target. The Compensation and Personnel Committee then multiplied this payout percentage by the number of PSUs originally granted to determine the numbers of PSUs earned, which were as follows:

  67. 2023 PSUs WITH PERFORMANCE PERIOD COMPLETED AS OF FISCAL YEAR ENDED DECEMBER 31, 2025

    | NEO | Earned PSUs (#) | | Giuseppina (Pina) Albo | 236,880 | | Craig Howie | 87,464 | | Adrian Daws | 40,874 | | Gemma Carreiro | 22,448 | | Alex Baker | 26,370 | | Megan Graves | 61,224 |

  68. 2023 PSUs WITH PERFORMANCE PERIOD COMPLETED AS OF FISCAL YEAR ENDED DECEMBER 31, 2025

    Underwriting return on capital is determined by a fraction, the numerator of which consists of (1) GAAP underwriting profit, plus (2) a catastrophe loss bank adjustment, plus (3) a reserve adjustment, plus (4) a loss portfolio transfer adjustment, plus (5) investment income on insurance float; and the denominator of which consists of risk-adjusted underwriting capital. The Compensation and Personnel Committee approves

  69. 2023 PSUs WITH PERFORMANCE PERIOD COMPLETED AS OF FISCAL YEAR ENDED DECEMBER 31, 2025

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  70. 2023 PSUs WITH PERFORMANCE PERIOD COMPLETED AS OF FISCAL YEAR ENDED DECEMBER 31, 2025

    underwriting return on capital for each of the three years in the performance period, and then compounds and annualizes them.

  71. COMPENSATION AND PERSONNEL COMMITTEE CONSULTANT

    COMPENSATION AND PERSONNEL COMMITTEE CONSULTANT Our Compensation and Personnel Committee may engage its own external compensation consultant to advise on the Company's compensation program generally, prepare reports that compare our compensation program to those of our peers and help ensure the competitiveness and appropriateness of our compensation. The Committee has sole authority to select, retain and terminate any consultants or advisors used to provide independent advice to the Compensation and Personnel Committee and evaluate executive compensation, including the sole authority to approve the fees and any other retention terms for such consultant or advisor. For the fiscal year ended December 31, 2025, the Committee retained Mercer (US) LLC ("Mercer") as the independent compensation consultant. Throughout the fiscal year, Mercer: •Conducted peer group benchmarking •Summarized proxy advisor feedback •Provided a regulatory and compensation trends update •Reviewed incentive practices for the short- and long-term incentive plan, including share usage •Reviewed Board of Directors’ compensation against the market •Reviewed executive benefits and perquisites Each year, our compensation consultant is required to submit a letter describing any conflicts of interest and other factors relating to its independence. The Compensation and Personnel Committee has determined that Mercer is independent and their work during the fiscal year ended December 31, 2025 did not raise any conflicts of interest. During the fiscal year ended December 31, 2025, Mercer’s fees for executive compensation consulting were $483,162. In addition to Mercer’s work on behalf of the Compensation and Personnel Committee, Mercer and its affiliates provide other non-executive compensation-related services to the Company. These services are approved by management, which oversees the specific areas of business for which the services are provided. The total amount paid for these other services in the fiscal year ended December 31, 2025 was $6,850,465. Most of these services are provided by other companies owned by Marsh (formerly Marsh & McLennan), the parent company of Mercer.

  72. PEER BENCHMARKING

    PEER BENCHMARKING In making determinations about executive compensation, the Compensation and Personnel Committee believes that obtaining relevant market data is important, because it serves as a reference point for making decisions and provides very helpful external context. When making decisions about the structure and component mix of our executive compensation program, the Compensation and Personnel Committee considers the structure and components of, and the amounts paid under, the executive compensation programs of other comparable companies, as derived from surveys, public filings, and other sources. The Compensation and Personnel Committee, with the assistance of a compensation consultant and considering peer groups used previously, reviewed peer sets for the fiscal year ended December 31, 2025. Because our business includes reinsurance and specialty insurance, the peer sets include companies with businesses that encompass one or more of those segments. The market data is used as a reference point and to provide information on the range of competitive pay levels and current compensation practices in our industry. The Compensation and Personnel Committee determined that the appropriate market reference was within the range for similar positions at peer companies. Executive officers’ total compensation may deviate from the level referenced to attract or retain key individuals or reflect their respective skills, experience, or performance. We believe that the compensation practices of these peer sets provided us with appropriate compensation reference points for establishing the compensation of our NEOs for the fiscal year ended December 31, 2025. Consistent with best practices for corporate governance, the Compensation and Personnel Committee reviews our competitive market information annually. Hamilton considers each element of total compensation and evaluates each NEO's competitive position on a total direct compensation basis, including base salary and short- and long-term incentive targets. When setting executive compensation, we consider market pay practices and pay levels using a compensation peer group and industry-leading surveys.

  73. 2025 Compensation Benchmarking Peer Group

    2025 Compensation Benchmarking Peer Group For purposes of comparing our executive compensation against the competitive market, the Compensation and Personnel Committee regularly reviews and considers the compensation levels and practices of a group of comparable companies. In August 2024, the Compensation and Personnel Committee conducted a reassessment of its compensation and performance peer groups with the assistance of Mercer, its independent compensation consultant, to set compensation for 2025. Argo Group International Holdings, Inc was removed from the 2025 peer group because it was acquired by Brookfield Reinsurance in 2023 and Palomar was removed because of its smaller size compared to the Company. The following companies were added to maintain an appropriate sample size and so Hamilton’s revenue is positioned closer to the median of the peer group: Assured Guaranty Ltd., ProAssurance Corporation, SiriusPoint, Ltd. and United Fire Group, Inc. In addition, Mercer recommended removing three companies because they are UK-based and do not provide the same level of compensation disclosure: Bealzey Group PLC, Hiscox Ltd. and Lancashire Holdings Limited. These companies will continue to be part of a supplemental reference group that is considered for compensation practices but not pay level benchmarking.

  74. 2025 Compensation Benchmarking Peer Group

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  75. 2025 Compensation Benchmarking Peer Group

    During the fiscal year ended December 31, 2025, the Compensation and Personnel Committee referenced the following compensation peer group for purposes of setting compensation and understanding the competitive market:

  76. 2025 Compensation Benchmarking Peer Group

    | Arch Capital Group Ltd. | Kinsale Capital Group, Inc. | SiriusPoint Ltd. | | Assured Guaranty Ltd. | Markel Group Inc. | Skyward Specialty Insurance Group, Inc. | | AXIS Capital Holdings Limited | ProAssurance Corporation | The Hanover Insurance Group, Inc. | | Everest Group, Ltd. | RenaissanceRe Holdings Ltd. | United Fire Group, Inc. | | James River Group Holdings, Ltd. | RLI Corp. | W.R. Berkley Corporation |

  77. 2025 Compensation Benchmarking Peer Group

    The Compensation and Personnel Committee regularly reviews the Company’s peer groups and considers advice from its compensation consultant. In selecting its compensation peer group, the Compensation and Personnel Committee seeks companies operating in similar industries, with a similar business model and similar size and geographic footprint.

  78. Termination And Change In Control Provisions

    Termination And Change In Control Provisions The Compensation and Personnel Committee believes that the long-term interests of shareholders are best served by providing reasonable protection to address potential change in control transactions in which NEOs may otherwise be distracted by their potential loss of employment in the event of a successful transaction. Under the terms of our 2013 Equity Incentive Plan and our 2023 Equity Incentive Plan, vesting is accelerated for the unvested portion of awards due to a change in control if, within 12 months following the change in control, the NEO’s employment is either terminated by the Company without cause or by the NEO for good reason. For PSUs, performance conditions would be deemed achieved based on the greater of actual performance or target at the time of the change in control, with the number of shares also to be fully vested. These are called “double trigger” arrangements (i.e., benefits under these arrangements are triggered only by the consummation of a change in control followed by the NEO’s termination of employment under certain specified circumstances within 12 months following the change in control). In addition, under the terms of our 2013 Equity Incentive Plan and our 2023 Equity Incentive Plan, if a change in control occurs and awards are not assumed or continued by the successor or surviving corporation, the unvested portion of any outstanding awards will generally vest on the date of the change in control, and the Compensation and Personnel Committee has discretion to settle such awards with cash. We do not provide excise tax “gross-ups” to any of our executive officers related to change-in-control payments.

  79. Severance Arrangements

    Severance Arrangements We provide severance benefit protection to our NEOs through our individual employment agreements with each such individual (in addition to the special provisions in connection with a change in control). The Compensation and Personnel Committee believes these severance payments and benefits are important from a recruiting perspective to provide some level of protection to our executive officers from having their employment terminated without cause or constructively terminated in connection with a change in control, or from experiencing a life-changing disability, and that the amounts are reasonable when compared with similar arrangements adopted by comparable companies. See “Executive Compensation Tables—Potential Payments Upon a Termination or Change in Control” below for further information.

  80. EQUITY GRANT TIMING

    EQUITY GRANT TIMING We typically grant our annual equity awards following the Compensation and Personnel Committee's fourth quarter meeting (held in the first quarter of the following fiscal year). We do not currently grant stock options or similar stock appreciation rights as part of our equity compensation program. Accordingly, during fiscal year ended December 31, 2025, (i) none of our NEOs were awarded stock options with an effective date during any period beginning four business days before the filing or furnishing of a Form 10-Q, Form 10-K, or Form 8-K that disclosed material nonpublic information, and ending one business day after the filing or furnishing of such reports, and (ii) we did not time the disclosure of material nonpublic information for the purpose of affecting the value of executive compensation. If stock options are granted in the future, the Company would aim to avoid granting such options in anticipation of releasing material nonpublic information that is likely to result in changes to the price of our common stock.

  81. Summary Compensation Table

    Summary Compensation Table The following table sets forth information concerning the compensation awarded to, earned by or paid to our NEOs by the Company in respect of our fiscal years ended December 31, 2025, 2024 and 2023.

  82. Summary Compensation Table

    | | | Salary(1) | Bonus (2) | Stock Awards (3) | Non-Equity Incentive Plan Compensation (4) | All Other Compensation (5) | Total | | Name and Principal Position | Year | ($) | ($) | ($) | ($) | ($) | ($) | | Giuseppina (Pina) Albo | 2025 | 1,300,000 | — | 3,900,000 | 3,640,000 | 136,000 | 8,976,000 | | Chief Executive Officer | 2024 | 1,300,000 | — | 3,575,000 | 3,640,000 | 130,000 | 8,645,000 | | | 2023 | 1,300,000 | 500,000 | 6,909,468 | 3,952,000 | 130,000 | 12,791,468 | | Craig Howie | 2025 | 660,000 | — | 1,536,000 | 1,732,500 | 21,000 | 3,949,500 | | Chief Financial Officer | 2024 | 640,000 | — | 1,380,000 | 1,675,000 | 10,265 | 3,705,265 | | | 2023 | 600,000 | 500,000 | 1,248,506 | 1,620,000 | 19,800 | 3,988,306 | | Adrian Daws (6) | 2025 | 660,000 | — | 827,609 | 1,379,728 | 245,085 | 3,112,422 | | Chief Executive Officer of Hamilton Re | 2024 | 491,684 | — | 732,105 | 1,108,188 | 48,370 | 2,380,347 | | | 2023 | 447,768 | 102,418 | 609,292 | 1,078,820 | 43,222 | 2,281,520 | | Gemma Carreiro | 2025 | 480,000 | — | 516,000 | 924,000 | 163,816 | 2,083,816 | | General Counsel | 2024 | 430,000 | — | 400,000 | 725,000 | 151,650 | 1,706,650 | | | 2023 | 400,000 | 500,000 | 351,636 | 580,000 | 187,205 | 2,018,841 | | Alex Baker(6)(7) | 2025 | 509,200 | — | 500,738 | 920,761 | 47,570 | 1,978,269 | | Chief Executive Officer of Hamilton Global Specialty | | | | | | | | | Megan Graves | 2025 | 650,000 | — | 1,079,500 | 1,501,500 | 190,241 | 3,421,241 | | Former Chief Executive Officer of Hamilton Re | 2024 | 635,000 | — | 944,000 | 1,422,000 | 208,670 | 3,209,670 | | | 2023 | 590,000 | 100,000 | 864,244 | 1,400,000 | 164,326 | 3,118,570 | | 1. Salary amounts represent each NEO’s annual base salary in effect as of December 31 of the applicable year. For 2025, the actual salaries paid to each NEO was as follows: $1,300,000, for Ms. Albo, $655,000, for Mr. Howie, $566,725, for Mr. Daws, $467,500 for Ms. Carreiro, $475,700 for Mr. Baker and $646,250 for Ms. Graves. | | | | | | | | | 2. The amounts shown in the Bonus column for 2023 reflect the bonus amounts received by the NEOs from a discretionary bonus pool established by the Board in connection with the initial public offering. For Mr. Daws, the amount was converted from British pound sterling (“GBP”) using the exchange rate on the payment date, which is $1.2490 per GBP on November 13, 2023. | | | | | | | | | 3. The amounts disclosed in the Stock Awards column represent the aggregate grant date fair value of RSUs and PSUs, computed in accordance with FASB Accounting Standards Codification Topic 718, excluding the effect of estimated forfeitures. Amounts disclosed in this column relating to RSUs and PSUs reflect the fair market value of a Class B common share on the date of grant multiplied by the number of shares underlying each award and assuming issuance at target for the PSUs (which reflects the probable achievement level of the applicable performance conditions). Assumptions, factors and methodologies used in our computations pursuant to ASC Topic 718 are set forth in Note 12 to our consolidated financial statements in our Annual Report on Form 10-K for the year ended December 31, 2025. The value of the PSU awards granted in 2025 at the grant date assuming that the maximum level of performance conditions was achieved was as follows: $3,900,000 for Ms. Albo, $1,536,000 for Mr. Howie, $1,079,500 for Ms. Graves, $827,609 for Mr. Daws, $500,738 for Mr. Baker and $516,000 for Ms. Carreiro. | | | | | | | | | 4. The amounts shown in the Non-Equity Incentive Plan Compensation column are comprised of amounts paid in respect of our annual cash incentive plan, as determined by the Compensation and Personnel Committee. Payments pursuant to the annual cash incentive plan are generally made early in the year following the year in which they are earned. Amounts in this column for 2025 are with respect to payments made pursuant to amounts earned in 2025 but paid in 2026 under the annual cash incentive plan. | | | | | | | | | 5. The amounts shown in this column for the fiscal year ended December 31, 2025 include (i) contributions by the Company to retirement plans or cash payments in lieu of contributions as follows: $136,000 for Ms. Albo, $21,000 for Mr. Howie, $66,750 for Ms. Graves, $56,673 for Mr. Daws, $47,571 for Mr. Baker and $46,750 for Ms. Carreiro; (ii) payments of the employee’s share of Bermudian government payroll and social insurance taxes: $104,406 for Ms. Graves, $117,066 for Ms. Carreiro and $34,581 for Mr. Daws (iii) reimbursement of Mr. Daws' relocation fees to Bermuda in the amount of $153,832 and (iv) reimbursement of Ms. Graves’ repatriation to the United States in connection with her retirement in the amount of $19,085. | | | | | | | | | 6. The U.S. dollar amounts in the table above for Mr. Daws for years 2023, 2024 and prior to September 2025 following his appointment to CEO of Hamilton Re, were converted from British pound sterling (“GBP”) using the 2025 average exchange rate, $1.3400 per GBP, for his salary and all other compensation. The amounts reflected for base salary represent the salary at year end. The U.S. dollar amounts in the table above for Mr. Baker, were converted from British pound sterling ("GBP") using the 2025 average exchange rate, $1.3400 per GBP, for his salary and all other compensation and the exchange rate of $1.319 per GBP, for his 2025 non-equity incentive plan compensation. The amounts reflected for base salary represent the salary at year end. | | | | | | | | | 7. Mr. Baker first became a named executive officer in 2025. In accordance with SEC rules, only compensation for fiscal year 2025 is required to be included in the Summary Compensation Table. | | | | | | | |

  83. Summary Compensation Table

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 64 |

  84. Grants of Plan-Based Awards in 2025

    Grants of Plan-Based Awards in 2025 The following table sets forth information about the non-equity incentive awards and equity-based awards granted by the Company to each of our NEOs in the fiscal year ended December 31, 2025.

  85. Grants of Plan-Based Awards in 2025

    | | | Estimated Future Payouts Under Non-Equity Incentive Plan Awards (1) | | | Estimated Future Payouts Under Equity Incentive Plan Awards (2) | | | All Other Stock Awards: Number of Shares of Stock or Units (3) | Grant Date Fair Value Of Stock Awards (4) | | | | Threshold | Target | Maximum | Threshold | Target | Maximum | | | | Name | Grant Date | ($) | ($) | ($) | (#) | (#) | (#) | (#) | ($) | | Giuseppina | | 0 | 2,080,000 | 4,160,000 | | | | | | | (Pina) Albo | 02/26/2025 | | | | | | | 105,921 | 1,950,006 | | | 02/26/2025 | | | | 52,961 | 105,921 | 211,842 | | 1,950,006 | | Craig Howie | | 0 | 990,000 | 1,980,000 | | | | | | | | 02/26/2025 | | | | | | | 41,717 | 768,010 | | | 02/26/2025 | | | | 20,859 | 41,717 | 83,434 | | 768,010 | | Adrian Daws (5) | | 0 | 795,760 | 1,591,520 | | | | | | | | 02/26/2025 | | | | | | | 22,478 | 413,820 | | | 02/26/2025 | | | | 11,239 | 22,478 | 44,956 | | 413,820 | | Gemma Carreiro | | 0 | 528,000 | 1,056,000 | | | | | | | | 02/26/2025 | | | | | | | 14,015 | 258,016 | | | 02/26/2025 | | | | 7,088 | 14,015 | 28,030 | | 258,016 | | Alex Baker(5) | | 0 | 547,614 | 1,095,228 | | | | | | | | 02/26/2025 | | | | | | | 13,600 | 250,376 | | | 02/26/2025 | | | | 6,800 | 13,600 | 27,200 | | 250,376 | | Megan Graves | | 0 | 910,000 | 1,820,000 | | | | | | | | 02/26/2025 | | | | | | | 29,319 | 539,763 | | | 02/26/2025 | | | | 14,660 | 29,319 | 58,638 | | 539,763 | | 1. The amounts disclosed in these columns reflect the target and maximum annual cash incentive opportunities of our NEOs for the fiscal year ended December 31, 2025. The amounts of the annual cash incentive opportunities depend on the annual base salary in effect at year end for each NEO. Below or at threshold performance on the financial metrics results in 0% payout. See “Compensation Discussion and Analysis—Compensation Program Components—Annual Cash Incentive Plan” for a detailed description of our annual cash incentive plan, including the criteria for determining the amounts payable. Actual 2025 annual cash incentive plan results (for 2025 performance) are reported in the “Non-Equity Incentive Plan Compensation” column of the Summary Compensation Table. The maximum award is 200% of target. Linear interpolation is used to determine the applicable payout amount between threshold and target and between target and maximum for results based on financial performance. | | | | | | | | | | | 2. Amounts disclosed in this column for grants made in February 2025 reflect the number of shares that may be realized under the PSUs granted to our NEOs in 2025 based on the 3-year annualized growth in book value per share as well as the 3-year average return on equity for the three-year performance period. See “Compensation Discussion and Analysis—Compensation Program Components—Long-Term Incentives—PSU Performance Metric” or a detailed description of the performance conditions for the PSUs. | | | | | | | | | | | 3. Amounts disclosed in this column reflect the number of RSUs granted to our NEOs in 2025. The RSUs granted in February 2025 as part of the annual equity grant vest over three years; one-third of the RSUs will vest on March 1 of each year for three years after the grant date, subject to continued service. | | | | | | | | | | | 4. The amounts shown in this column represent the grant date fair value of RSUs and PSUs, computed in accordance with ASC Topic 718, excluding the effect of estimated forfeitures. Amounts disclosed in this column relating to RSUs reflect the fair market value of a Class B common share on the date of grant multiplied by the number of shares underlying each award and assuming issuance at target for the PSUs (which reflects the probable achievement level of the performance conditions). Assumptions, factors and methodologies used in our computations pursuant to ASC Topic 718 are set forth in Note 12 to our consolidated financial statements in our Annual Report on Form 10-K for the year ended December 31, 2025. Regardless of the value on the grant date, the actual value depends on the market value of our Class B common shares on a date in the future when the RSUs and PSUs vest. | | | | | | | | | | | 5. The U.S. dollar amounts in the table above for Mr. Daws and Mr. Baker, were converted from British pound sterling (“GBP”) using the 2025 average exchange rate, $1.3400 per GBP, for their non-equity incentive awards. The U.S. dollar amounts in the table above are calculated using a prorated apportionment of their salaries pre and post their new appointments effective September 1, 2025. | | | | | | | | | |

  86. Grants of Plan-Based Awards in 2025

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 65 |

  87. Outstanding Equity Awards at Fiscal Year Ended December 31, 2025

    Outstanding Equity Awards at Fiscal Year Ended December 31, 2025 The following table sets forth information about the outstanding equity awards to acquire our Class B common shares held by each of our NEOs as of the fiscal year ended December 31, 2025.

  88. Outstanding Equity Awards at Fiscal Year Ended December 31, 2025

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 68 |

  89. Outstanding Equity Awards at Fiscal Year Ended December 31, 2025

    | | | | Stock Awards | | | | | | | | Number of shares or Units That Have Not Vested (1) | Market Value of Shares or Units that Have Not Vested (2) | Equity Incentive Plan Awards: Number of Unearned Shares, Units or Other Rights that Have Not Vested (3) | Equity Incentive Plan Awards: Market or Payout Value of Unearned Shares, Units, or Other Rights that Have Not Vested (4) | | Name | Award Type | Grant Date | (#) | ($) | (#) | ($) | | Giuseppina (Pina) Albo | RSU | 03/10/2023(5) | 39,480 | 1,101,492 | | | | | | 11/10/2023(6) | 116,667 | 3,255,009 | | | | | | 03/05/2024(7) | 82,184 | 2,292,934 | | | | | | 02/26/2025(8) | 105,921 | 2,955,196 | | | | | PSU | 03/10/2023(9) | | | 236,880 | 6,608,952 | | | | 11/10/2023(10) | | | 200,000 | 5,580,000 | | | | 03/05/2024(11) | | | 246,552 | 6,878,801 | | | | 02/26/2025(12) | | | 211,842 | 5,910,392 | | Craig Howie | RSU | 03/10/2023(5) | 14,578 | 406,726 | | | | | | 03/05/2024(7) | 31,724 | 885,100 | | | | | | 02/26/2025(8) | 41,717 | 1,163,904 | | | | | PSU | 03/10/2023(9) | | | 87,464 | 2,440,246 | | | | 03/05/2024(11) | | | 95,172 | 2,655,299 | | | | 02/26/2025(12) | | | 83,434 | 2,327,809 | | Adrian Daws | RSU | 03/10/2023(5) | 6,813 | 190,083 | | | | | | 03/05/2024(7) | 16,830 | 469,557 | | | | | | 02/26/2025(8) | 22,478 | 627,136 | | | | | PSU | 03/10/2023(9) | | | 40,874 | 1,140,385 | | | | 03/05/2024(11) | | | 50,490 | 1,408,671 | | | | 02/26/2025(12) | | | 44,956 | 1,254,272 | | Gemma Carreiro | RSU | 03/10/2023(5) | 3,741 | 104,374 | | | | | | 03/05/2024(7) | 9,195 | 256,541 | | | | | | 02/26/2025(8) | 14,015 | 391,019 | | | | | PSU | 03/10/2023(9) | | | 22,448 | 626,299 | | | | 03/05/2024(11) | | | 27,586 | 769,649 | | | | 02/26/2025(12) | | | 28,030 | 782,037 | | Alex Baker | RSU | 03/10/2023(5) | 4,395 | 122,621 | | | | | | 03/05/2024(7) | 10,518 | 293,452 | | | | | | 02/26/2025(8) | 13,600 | 379,440 | | | | | PSU | 03/10/2023(9) | | | 26,370 | 735,723 | | | | 03/05/2024(11) | | | 31,556 | 880,412 | | | | 02/26/2025(12) | | | 27,200 | 758,880 | | Megan Graves(13) | RSU | 03/10/2023(5) | 10,204 | 284,692 | | | | | | 03/05/2024(7) | 21,701 | 605,458 | | | | | | 02/26/2025(8) | 29,319 | 818,000 | | | | | PSU | 03/10/2023(9) | | | 61,224 | 1,708,150 | | | | 03/05/2024(11) | | | 65,104 | 1,816,402 | | | | 02/26/2025(12) | | | 58,638 | 1,636,000 |

  90. Outstanding Equity Awards at Fiscal Year Ended December 31, 2025

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 69 |

  91. Outstanding Equity Awards at Fiscal Year Ended December 31, 2025

    | 1. Amounts disclosed in this column reflect the number of unvested RSUs granted that had not vested as of December 31, 2025. See “Executive Compensation Tables—Potential Payments Upon Termination or Change in Control” for a summary of the treatment of RSUs upon death, disability, termination or change in control. | | 2. Amounts disclosed in this column reflect the market value of the RSUs using the fair market value of a Class B common share on December 31, 2025, $27.90 , multiplied by the number of shares underlying each award. | | 3. Amounts disclosed in this column reflect the number of unvested PSUs that are subject to open performance periods as of December 31, 2025. See “Executive Compensation Tables—Potential Payments Upon Termination or Change in Control” for a summary of the treatment of PSUs upon death, disability, termination or change in control. | | 4. Amounts disclosed in this column reflect the market value of the unvested PSUs using the fair market value of a Class B common share on December 31, 2025, $27.90, multiplied by the number of shares underlying each award (assuming issuance at target, which reflects the probable achievement level of the applicable performance conditions). | | 5. The RSUs granted to our NEOs on March 10, 2023 vest in three equal annual installments on March 1 of each of 2024, 2025, and 2026, respectively, subject to the NEO’s continued service through each vesting date. | | 6. The RSUs granted to Ms. Albo on November 10, 2023 cliff vest on the third anniversary of the grant date, subject to her continued service through the vesting date. | | 7. The RSUs granted to our NEOs on March 5, 2024 vest in three equal annual installments on March 1 of each of 2025, 2026, and 2027, respectively, subject to the NEO’s continued service through each vesting date. | | 8. The RSUs granted to our NEOs on February 26, 2025 vest in three equal annual installments on March 1 of each of 2026, 2027, and 2028, respectively, subject to the NEO’s continued service through each vesting date. | | 9. The PSUs granted to our NEOs on March 10, 2023 are earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2025. The amounts reflect the maximum achievement of 200% (which reflects the achievement level of the applicable performance conditions). | | 10. The PSUs granted to Ms. Albo on November 10, 2023 are earned and vest based on the percentage increase in the price of our Class B common shares during the three-year period following the grant date ranging from 0% of the PSUs being earned and vesting if there is no (or negative) change in the value of our Class B common shares during the measurement period up to 100% of the PSUs being earned and vesting if the price of our Class B common shares doubles during the measurement period, with the number of PSUs that vest being determined based on linear interpolation for increases between 0% and 100%. | | 11. The PSUs granted to our NEOs on March 5, 2024 are earned based on the 3-year annualized growth in book value per share as well as the 3-year average return on equity for the 3-year performance period ending on December 31, 2026. The amounts reflect achievement at maximum as of December 31, 2025 (which reflects the probable achievement level of the applicable performance conditions). | | 12. The PSUs granted to our NEOs on February 26, 2025 are earned based on the 3-year annualized growth in book value per share as well as the 3-year average return on equity for the 3-year performance period ending on December 31, 2027. The amounts reflect achievement at maximum as of December 31, 2025 (which reflects the probable achievement level of the applicable performance conditions). | | 13. Per Ms. Graves’ retirement agreement, her unvested RSUs and PSUs will continue to vest subject to the terms of such agreement. |

  92. Outstanding Equity Awards at Fiscal Year Ended December 31, 2025

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 70 |

  93. Stock Vested in Fiscal Year Ended December 31, 2025

    Stock Vested in Fiscal Year Ended December 31, 2025 The following table sets forth information about the value realized by each of our NEOs as a result of RSUs that vested and PSUs that were earned during the fiscal year ended December 31, 2025.

  94. Stock Vested in Fiscal Year Ended December 31, 2025

    | | Stock Awards | | | | Number of Shares | Value Realized | | | Acquired on Vesting (1) | on Vesting (2) | | Name | (#) | ($) | | Giuseppina (Pina) Albo | 389,799 | 8,428,573 | | Craig Howie | 135,535 | 2,916,257 | | Adrian Daws | 77,603 | 1,704,205 | | Gemma Carreiro | 53,514 | 1,220,648 | | Alex Baker | 44,682 | 1,060,857 | | Megan Graves | 97,183 | 2,071,158 | | 1. The amounts shown in this column represent the number of RSUs that vested and the PSUs that were earned for each NEO during the fiscal year ended December 31, 2025. | | | | 2. The amounts shown in this column reflect the value realized upon vesting of the RSUs and the earning of the PSUs for each NEO, as calculated based on the price of our Class B common shares on the vesting date, multiplied by the number of shares vested or earned on such date. | | |

  95. Pension Benefits

    Pension Benefits We do not currently sponsor or maintain any defined benefit pension benefit or retirement benefit plans providing specified retirement payments and benefits for our NEOs or any of our other employees.

  96. Nonqualified Defined Contribution and Other Nonqualified Deferred Compensation Plans

    Nonqualified Defined Contribution and Other Nonqualified Deferred Compensation Plans We do not currently sponsor or maintain any nonqualified defined contribution or other nonqualified deferred compensation plans for the benefit of our employees.

  97. Potential Payments Upon Termination or Change in Control

    Potential Payments Upon Termination or Change in Control As of the end of the fiscal year ended December 31, 2025, our NEOs were eligible to receive severance upon certain terminations of employment in accordance with their employment agreements, in each case, as described below. Each employment agreement imposes restrictive covenants, including intellectual property assignment, confidentiality, non-disparagement, non-competition, and non-solicitation. Except as otherwise described below, the restricted period for the non-competition and non-solicitation provisions includes the term of employment plus a post-employment period of six (6) months following the date of termination (twelve (12) months for Ms. Albo), or twelve (12) months if the termination is in connection with a change in control.

  98. Potential Payments Upon Termination or Change in Control

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 71 |

  99. Pay Versus Performance Table and Disclosures

    Pay Versus Performance Table and Disclosures In accordance with rules adopted by the SEC pursuant to the Dodd-Frank Wall Street Reform and Consumer Protection Act of 2010, we provide the following disclosure regarding executive compensation for our principal executive officer (“PEO”) and Non-PEO NEOs and Company performance for the fiscal years listed below. The Compensation and Personnel Committee did not consider the pay versus performance disclosure below in making its pay decisions for any of the years shown.

  100. Pay Versus Performance Table and Disclosures

    | Year | Summary Compensation Table Total for PEO(1) ($) | Compensation Actually Paid to PEO(1),(2),(3) ($) | Average Summary Compensation Table Total for Non-PEO NEOs(1)($) | Average Compensation Actually Paid to Non-PEO NEOs(1)(2)(3) ($) | Value of Initial Fixed $100 Investment based on:(4) | | Net Income ($ Millions) | Combined Ratio (%)(5) | | | | | | | TSR ($) | Peer Group TSR ($) | | | | 2025 | 8,976,000 | 24,792,818 | 2,909,050 | 5,422,742 | 186.00 | 152.78 | 577 | 92.9% | | 2024 | 8,645,000 | 17,224,450 | 2,751,683 | 4,461,080 | 126.87 | 138.79 | 400 | 91.3% | | 2023 | 12,791,468 | 15,585,998 | 2,851,809 | 3,489,754 | 99.67 | 102.44 | 280 | 90.1% |

  101. Pay Versus Performance Table and Disclosures

    1.Non-PEOs included in the above compensation columns reflect the following:

  102. Pay Versus Performance Table and Disclosures

    | Fiscal Year | PEO | Non-PEOs | | 2025 | Giuseppina (Pina) Albo | Craig Howie; Megan Graves; Adrian Daws; Gemma Carreiro; Alex Baker | | 2024 | Giuseppina (Pina) Albo | Craig Howie; Megan Graves; Adrian Daws; Gemma Carreiro | | 2023 | Giuseppina (Pina) Albo | Craig Howie; Megan Graves; Adrian Daws; Gemma Carreiro |

  103. Pay Versus Performance Table and Disclosures

    2.The amounts shown for Compensation Actually Paid have been calculated in accordance with Item 402(v) of Regulation S-K and do not reflect compensation actually earned, realized or received by the Company's NEOs. These amounts reflect the Summary Compensation Table Total with certain adjustments as described in footnote 3 below. 3.Compensation Actually Paid reflects the exclusions and inclusions of certain amounts for the PEO and the Non-PEO NEOs as set forth below. Equity values are calculated in accordance with FASB ASC Topic 718. Amounts in the Exclusion of Stock Awards column are the amounts from the Stock Awards columns set forth in the Summary Compensation Table. The fair value or change in fair value, as applicable, of equity awards in the “Compensation Actually Paid” columns was determined by reference to (1) for time-based vesting RSU awards, closing price on the applicable year-end date, or, in the case of vesting dates, the closing price on the applicable vesting dates, (2) for performance-based RSU awards (excluding awards with market-based vesting conditions), the same valuation methodology as RSU awards above except year-end values are multiplied by the probability of achievement as of each such date, (3) for awards with market-based vesting conditions, the fair value calculated by a Monte Carlo simulation model as of the applicable year-end date(s) and (4) VAP, which are valued the same as other time-based RSU awards, Compensation Actually Paid to our PEO and the average Compensation Actually Paid to non-PEOs reflects the following adjustments from the compensation reported in the “Total” column of the Summary Compensation Table:

  104. Pay Versus Performance Table and Disclosures

    | | Fiscal 2025 | | | | PEO | Average Non-PEO | | Total Reported in Summary Compensation Table | 8,976,000 | 2,909,050 | | Less, value of equity awards reported in Summary Compensation Table | (3,900,000) | (891,969) | | Plus, year-end value of awards granted in fiscal year that are unvested and outstanding at the end of the fiscal year | 8,865,588 | 2,027,699 | | Plus, change in fair value of prior year awards that are unvested and outstanding at end of fiscal year | 9,813,262 | 1,131,789 | | Plus, fair value of awards granted in fiscal year and that vested in this fiscal year | 0 | 0 | | Plus, change in fair value of prior year awards that vested in this fiscal year | 1,037,968 | 246,174 | | Less, fair value of prior year awards that failed to vest this fiscal year | 0 | 0 | | Total Adjustments | 15,816,818 | 2,513,693 | | Compensation Actually Paid | 24,792,818 | 5,422,742 |

  105. Pay Versus Performance Table and Disclosures

    4.The Peer Group TSR set forth in this table utilizes the S&P 500 Property & Casualty Insurance Index, which we also utilize in the stock performance graph required by Item 201(e) of Regulation S-K included in our Annual Report for the year ended December 31, 2025. The comparison assumes $100 was invested for the period starting November 10, 2023 and ending on December 31, 2025 in the Company and in the S&P 500 Property & Casualty Insurance Index, respectively, including reinvestment of dividends. Historical stock performance is not necessarily indicative of future stock performance. .

  106. Pay Versus Performance Table and Disclosures

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 76 |

  107. Pay Versus Performance Table and Disclosures

    5.We determined Combined Ratio to be the most important financial performance measure used to link Company performance to Compensation Actually Paid to our PEO and Non-PEO NEOs in 2025. Please refer to the section of this proxy statement titled "Financial Measure (60%)" section for an explanation of Combined Ratio. This performance measure may not have been the most important financial performance measure in prior years and we may determine a different financial performance measure to be the most important financial performance measure in future years.

  108. Relationship Between PEO and Non-PEO Compensation Actually Paid and Total Shareholder Return

    Relationship Between PEO and Non-PEO Compensation Actually Paid and Total Shareholder Return The following chart sets forth the relationship between compensation actually paid to our PEO, the average of compensation actually paid to our Non-PEOs, and the Company’s cumulative total shareholder return ("TSR") over the three most recently completed fiscal years and the S&P 500 Property & Casualty Insurance Index TSR over the same period.

  109. Relationship Between PEO and Non-PEO Compensation Actually Paid and Total Shareholder Return

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 77 |

  110. Relationship Between PEO and Non-PEO Compensation Actually Paid and Net Income

    Relationship Between PEO and Non-PEO Compensation Actually Paid and Net Income The following chart sets forth the relationship between compensation actually paid to our PEO, the average of compensation actually paid to our Non-PEOs, and our net income during the three most recently completed fiscal years.

  111. Relationship Between PEO and Non-PEO Compensation Actually Paid and Net Income

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 78 |

  112. Relationship Between PEO and Non-PEO Compensation Actually Paid and Combined Ratio

    Relationship Between PEO and Non-PEO Compensation Actually Paid and Combined Ratio The following chart sets forth the relationship between compensation actually paid to our PEO, the average of compensation actually paid to our Non-PEOs, and our combined ratio during the three most recently completed fiscal years.

  113. CEO Pay Ratio

    CEO Pay Ratio As required by Section 953(b) of the Dodd-Frank Act and Item 402(u) of Regulation S-K (“Item 402(u)”), the Company is providing the following reasonable estimate of the ratio of the compensation of Ms. Albo, our CEO, to that of a median employee, calculated in a manner consistent with Item 402 (u). For the fiscal year ended December 31, 2025: •The median employee's annual total compensation was $156,985. •The annual total compensation of our CEO, Ms. Albo, was $8,976,000. •Based on this information, the ratio of the annual total compensation of our CEO to that of the median employee was 57.18 to one. We determined that as of December 31, 2025, our employee population consisted of 646 individuals. To identify our “median” employee, we obtained the annualized bases salary amounts from our internal compensation system for each employee in our global population. Base salary amounts for employees paid in currencies other than U.S. dollars were converted to dollars based on the average 2025 foreign exchange rates as of December 31, 2025. We then ranked the resulting base salaries of all employees to determine our median employee. Once we identified our median employee, we combined all of the elements of the median employee’s compensation in accordance with the requirements of Item 402(c)(2)(x) of Regulation S-K relating to the summary compensation table. With respect to the annual total compensation of Ms. Albo, we used the amount reported in the “Total” column of our Summary Compensation Table contained in this proxy statement.

  114. CEO Pay Ratio

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 80 |

  115. 2025 Director Compensation

    2025 Director Compensation In accordance with our compensation program for non-employee directors, non-employee members of our Board receive the following compensation for service: Annual Compensation Package: $250,000, consisting of: •$150,000 in the form of RSUs granted on the date of the Annual General Meeting. These RSUs cliff vest on the earlier of one year or the date of the subsequent Annual General Meeting. •$100,000 paid in cash on a quarterly, pro rata basis. •Non-employee directors may elect to defer receipt of 50% or 100% of their RSUs. Additional Compensation: •Chair of the Board: An additional $175,000 (cash), bringing the Chair’s total annual compensation to $425,000, exclusive of any additional compensation payable for committee assignments or other Board responsibilities. •Chair of Audit Committee: An additional $50,000 (cash). •Chair of Compensation and Personnel Committee: An additional $25,000 (cash). •Chair of other committees: An additional $20,000 (cash). •Directors serving on the board of an operating subsidiary: An additional $20,000 (cash or Company shares, at the director’s election). Non-employee directors who do not serve as committee chairs do not receive additional fees for committee service. We also reimburse directors for reasonable and necessary out-of-pocket expenses incurred in attending meetings or performing other services in their capacity as directors. Share Ownership Guidelines: To strengthen alignment with shareholders and demonstrate sound governance, non-employee directors must, within five years of appointment, hold Company shares equal to at least five times the value of their annual retainer (excluding any portion paid in Company shares and committee chair or subsidiary board fees).

  116. 2025 Director Compensation

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 81 |

  117. Director Summary Compensation Table

    | | Fees Earned or Paid in Cash (1) | Stock Awards (2) | Total | | Name | ($) | ($) | ($) | | William C. Freda (3) | 41,667 | — | 41,667 | | David Brown | 295,000 | 150,000 | 445,000 | | Stephen Pacala | 120,000 | 150,000 | 270,000 | | Marvin Pestcoe | 140,000 | 150,000 | 290,000 | | Barclay Simmons | 100,000 | 150,000 | 250,000 | | John Gauthier | 125,000 | 150,000 | 275,000 | | Henna Karna | 112,500 | 150,000 | 262,500 | | Terri Vaughan | 100,000 | 150,000 | 250,000 | | Neil Patterson | 150,000 | 150,000 | 300,000 | | Karen Green (4) | 66,667 | 150,000 | 216,667 | | David Priebe (4) | 66,667 | 150,000 | 216,667 | | Brad Cooper (5) | — | — | — | | H. Hawes Bostic, III(6) | — | — | — | | 1. Annual director compensation for the fiscal year ended December 31, 2025 was comprised of $100,000 in cash and RSUs with a grant date value of $150,000, which are scheduled to vest at the Annual General Meeting. The amounts disclosed in this column reflect the amount of cash compensation received by each non-employee director. Additional compensation for the chair of the Board is $175,000. Additional compensation for chairs of the various committees are: $50,000 (Audit chair), $25,000 (Compensation and Personnel chair), and $20,000 (chairs of all other committees). All additional chair compensation is paid in cash. | | | | | 2. The amounts disclosed in the Stock Awards column represent the aggregate grant date fair value, computed in accordance with ASC Topic 718, of the Company Class B common shares issued. Amounts disclosed in this column reflect the number of shares issued multiplied by the grant date fair value of a Class B common share on the grant date. These Class B common shares were issued in May 2025, and will vest on the earlier of the one-year anniversary of the grant date and the date of the subsequent Annual General Meeting. The aggregate number of stock awards outstanding for each non‑employee director as of December 31, 2025 consisted solely of the 7,187 unvested RSUs granted at the Annual General Meeting in May 2025. No stock options were outstanding for any non‑employee director as of December 31, 2025. | | | | | 3. Mr. Freda retired from the Board on May 15, 2025 . His annual fee is prorated based on his service period. | | | | | 4. Ms. Green and Mr. Priebe were elected to the Board on May 15, 2025 . Their annual fees are prorated based on their respective service periods. | | | | | 5. Mr. Cooper serves on the Board without compensation as the Hopkins Holdings Shareholder Director. | | | | | 6. Mr. Bostic served on the Board without compensation as the Magnitude Shareholder Director until February 20, 2026, when Marc Roston replaced him as the Magnitude Shareholder Director. | | | |

  118. Other Underwriting Expense Ratio

    Other Underwriting Expense Ratio Other Underwriting Expense Ratio is a measure of the other underwriting expenses (net of third party fee income) incurred by the Company and is expressed as a percentage of net premiums earned.

  119. Other Underwriting Expense Ratio

    | Hamilton Insurance Group, Ltd. | 2026 Proxy Statement | 94 |