DEF 14A of Hamilton Insurance Group, Ltd., Mar 27, 2025

DEF 14A of Hamilton Insurance Group, Ltd.

Filed Mar 27, 2025 · FY20240001593275-25-000124

Open on EDGAR

  1. Board of Directors

    Board of Directors 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, and as such, the size and composition of the Board will be determined from time to time by balancing the need for diverse perspectives and expertise, with the practicalities of efficient corporate governance. In addition to the above, we entered into a Shareholders Agreement dated November 14, 2023 (the "Shareholders Agreement") with certain Shareholders who, together with their affiliates, owned at least 5% of our issued and outstanding common shares as at the date of the Shareholders Agreement. These Shareholders inter alia include: Sango Holdings (being Sango Hoken Holdings, LLC), Hopkins Holdings (being Hopkins Holdings, LLC) and 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), including any permitted transferee of any of the foregoing. The Shareholders Agreement provides that each such Shareholder has the right to appoint a director to the Board of Directors (each a "Shareholder Director"), subject to the maintenance of certain ownership thresholds. See "Certain Relationships and Related Party Transactions". The remaining directors are elected by the holders of our Class B common shares (“Class B Directors”) 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 H. Hawes Bostic, III and Bradley Cooper and the Class B Directors are David A. Brown, Giuseppina (Pina) Albo, William C. Freda, John J. Gauthier, Anu (Henna) Karna, Stephen W. Pacala, Neil Patterson, Marvin Pestcoe, Everard Barclay Simmons and Therese Vaughan. The former Hopkins Holdings director, Antonio Ursano, Jr., resigned from the Board of Directors effective June 1, 2024 following which Mr. Cooper was appointed as its Shareholder Director. 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. Nine of these individuals are incumbent directors and were elected by the Shareholders at our 2024 annual general meeting. The two other individuals, Karen Ann Green and David Priebe, who are being nominated for the first time, were recommended by the Nominating and Corporate Governance Committee as potential directors following a comprehensive search process. This process incorporated the valuable industry contacts of our executive officers, which played a crucial role in identifying these qualified candidates. Our bye-laws provide that our Board of Directors may appoint such officers as it may determine. This provides the Board of Directors 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 of Directors has concluded that our current leadership structure is appropriate at this time. However, our Board of Directors will continue to periodically review our leadership structure and may make such changes in the future as it deems appropriate.

  2. Board of Directors

    | Hamilton Insurance Group, Ltd. | 2025 Proxy Statement | 5 |

  3. Class B Director Nominees

    Class B Director Nominees The Nominating and Corporate Governance Committee has recommended, and our Board of Directors has approved, David A. Brown, Giuseppina (Pina) Albo, John J. Gauthier, Karen Ann Green, Anu (Henna) Karna, Stephen W. Pacala, Neil Patterson, Marvin Pestcoe, David Priebe, Everard Barclay Simmons and Therese Vaughan 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 2026 annual general meeting or until his or her successor is duly elected and qualified.

  4. Class B Director Nominees

    | Hamilton Insurance Group, Ltd. | 2025 Proxy Statement | 8 |

  5. Class B Director Nominees

    | Name | Age | Committees | Position | Since | | David A. Brown | 67 | Compensation and Personnel and Underwriting and Risk | Independent Director | 2013 | | Giuseppina (Pina) Albo | 62 | | CEO and Director | 2018 | | John J. Gauthier | 63 | Compensation and Personnel and Investment | Independent Director | 2023 | | Karen Ann Green | 57 | Proposed to be on Audit, Underwriting and Risk and Compensation and Personnel | Independent Director | First-time Nominee | | Anu (Henna) Karna | 48 | Audit, Nominating and Governance and Underwriting and Risk | Independent Director | 2023 | | Stephen W. Pacala | 68 | Compensation and Personnel, Nominating and Governance and Underwriting and Risk | Independent Director | 2013 | | Neil Patterson | 61 | Audit and Nominating and Governance | Independent Director | 2024 | | Marvin Pestcoe | 64 | Audit, Underwriting and Risk and Investment | Independent Director | 2020 | | David Priebe | 66 | Proposed to be on Audit and Underwriting and Risk | Independent Director | First-time Nominee | | Everard Barclay Simmons | 52 | Audit and Investment | Independent Director | 2023 | | Therese Vaughan | 68 | Nominating and Corporate Governance and Underwriting and Risk | Independent Director | 2024 |

  6. Class B Director Nominee Biographies

    Class B Director Nominee Biographies

  7. 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 of Directors. He also has served as non-executive Chair of Hamilton Re, Ltd. (Hamilton Re) 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 experience serving on the boards of various organizations. Mr. Brown has served as Deputy Chair at the Bermuda Stock Exchange since 2020 (and previously held the role of Chair from 2000 to 2020), as Chair of the Board of Argus Insurance Group from February 2020 until December 2024, as a director of MIAX Pearl Exchange since April 2021 and as Chairman of Bermuda Commercial Bank since July 2021. Mr. Brown is also a member of the Institute of Chartered 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 expertise in accounting qualifies him to serve on the Company’s Board of Directors. |

  8. Class B Director Nominee Biographies

    | Hamilton Insurance Group, Ltd. | 2025 Proxy Statement | 9 |

  9. 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 of Directors 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 Directors 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 of Directors. |

  10. 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, The Hartford Funds, and Middlesex (CT) Health Systems. Mr. Gauthier served on the Board of Directors 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 of Directors. |

  11. Class B Director Nominee Biographies

    | Hamilton Insurance Group, Ltd. | 2025 Proxy Statement | 10 |

  12. Class B Director Nominee Biographies

    | Karen Ann Green | Ms. Green is being nominated for the first time as a potential director of the Company. She is the Senior Independent Director of Phoenix Group Holdings PLC, and a Non-Executive Director of Admiral Insurance Group PLC, and Great Portland Estates PLC, (where she is also the SID designate effective April 4, 2025). She is also a Non-Executive Director of the Miller broking business (Miller Insurance Services LLP and Ben Nevis CleanCo Ltd) and of Tucano Holdings Jersey Ltd (the TMF Group. 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 GE Capital in London. She started her career as an investment banker with Baring Brothers and then Schroders. She is a Trustee of Wellbeing of Women, and an Advisor to Cytora Ltd. She was previously Vice President of the Insurance Institute of London. We believe that Ms. Green's extensive financial services experience as well as in leadership positions qualifies her to serve on the Company's Board of Directors. |

  13. Class B Director Nominee Biographies

    | Anu (Henna) Karna | Ms. 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. Most recently, Dr. Karna served as the General Manager, Managing Director, Global Insurance & Risk Management Solutions at Google from November 2020 to March 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 is a member of the board of directors of Essent Group Ltd. 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 of Directors. |

  14. Class B Director Nominee Biographies

    | Hamilton Insurance Group, Ltd. | 2025 Proxy Statement | 11 |

  15. Class B Director Nominee Biographies

    | Stephen W. Pacala | Mr. Pacala has served as a director of the Company since 2013. He has also served as a Professor and Director at Princeton University since 1992. From 1982 to 1992 he served as an associate professor at the University of Connecticut. Mr. Pacala was also a member of President Biden’s Council of Advisors on Science and Technology, the American Academy of Arts and Sciences, and the National Academy of Sciences. Mr. Pacala is a previous recipient of the MacArthur Award, Mercer Award and the David Starr Jordan Prize. Mr. Pacala holds a Bachelor of Arts degree from Dartmouth College and a Ph.D. in biology from Stanford University. We believe Mr. Pacala’s extensive experience in climate-related matters and in leadership positions qualifies him to serve on the Company’s Board of Directors. |

  16. 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 a recently 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 KPMG’s regional firm; The KPMG Islands Group (KIG). In this capacity, he was also a member of KPMG’s Board of Directors for its European, Middle East and Africa (EMA) 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. BICL 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. We believe Mr. Patterson's extensive financial and audit experience qualifies him to serve on the Company’s Board of Directors. |

  17. Class B Director Nominee Biographies

    | Hamilton Insurance Group, Ltd. | 2025 Proxy Statement | 12 |

  18. 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 and a director of Aisix Solutions (formerly Minerva Intelligence). 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 and investing and business leadership experience qualifies him to serve on the Company’s Board of Directors. |

  19. Class B Director Nominee Biographies

    | David Priebe | Mr. Priebe is being nominated for the first time as a potential director of the Company. 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 of Directors. |

  20. 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 a Bermuda law firm 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 Argus Group Holdings 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 of Directors. |

  21. Class B Director Nominee Biographies

    | Hamilton Insurance Group, Ltd. | 2025 Proxy Statement | 13 |

  22. 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 of Directors. |

  23. Class B Director Nominee Biographies

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

  24. Class B Director Nominee Biographies

    | Hamilton Insurance Group, Ltd. | 2025 Proxy Statement | 14 |

  25. 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 2026 annual general meeting of Shareholders must follow the notice procedures described in “Shareholder Proposals for the 2026 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 •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.

  26. Compensation Philosophy

    Compensation Philosophy Our compensation philosophy is performance-based and focuses on aligning the financial interests of our executive officers, including our NEOs, with those of our Shareholders. Key components of our compensation philosophy are as follows: Attract, motivate, and retain key talent needed to continue Hamilton’s growth: We recruit talent with diverse experience, expertise, capabilities, and backgrounds to lead the profitable growth of our business and to execute our strategy. We reference the amounts and components of executive officer compensation in the companies in our compensation peer groups in recruiting our executive officers and determining competitive pay levels. Provide a significant portion of total pay in variable pay that aligns actual payments with performance outcomes (pay for performance): We structure the compensation of our executive officers to have a significant portion that is variable and at-risk based on Company performance, given the executives’ greater ability to influence the achievements of the enterprise as a whole. The variable components include annual cash incentives and long-term equity incentives. As actual variable compensation earned is tied directly to the achievement of financial, strategic, and business goals and our equity value, with upside potential when executives exceed target goals, the higher allocation to variable pay fosters a pay-for-performance culture. Provide rewards for attainment of tangible objectives, while also considering the external context: We have designed our executive compensation program to incentivize our executive officers to achieve goals that advance our strategic and business objectives and increase Shareholder value by closely linking Company performance and their individual performance to the compensation they earn. We specify clear and measurable quantitative and qualitative goals that, in combination and if achieved, are designed to elevate our results and returns to Shareholders. We strive for our reward offerings to be market competitive, aligned with market practice and considerate of Shareholder interests. Align executive officers’ interests with those of the Company and its Shareholders, via equity-based and other long-term incentive compensation: Equity-based and other long-term incentive compensation constitutes a significant portion of our executive officers’ overall compensation. We use equity as the primary form for long-term incentive opportunities to motivate and reward executive officers to (i) achieve multi-year strategic goals and (ii) deliver sustained long-term value to Shareholders. Using equity for long-term incentives creates strong alignment between the interests of executive officers and those of our Shareholders. It provides executive officers with a common interest with Shareholders in share price performance and fosters an ownership culture among executive officers by making them Shareholders with a personal stake in the value they are being motivated 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 are expected to 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.

  27. ANNUAL INCENTIVE OPPORTUNITY

    ANNUAL INCENTIVE OPPORTUNITY Our Compensation and Personnel Committee used Company financial and strategic and operational performance goals for its 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, 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 bonus 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 bonus 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 focused 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, alignment with our corporate values and the execution of our sustainability strategy For the financial goal (60%), the combined ratio for the fiscal year ended December 31, 2024 was 91.3%. This performance equated to 163% of target achievement. For the strategic and operational goals (40%), the Compensation and Personnel Committee determined that strategic growth (20%) was achieved at 200% of target, technology enablement (10%) was achieved at 75% and magnet for talent (10%) was achieved at 150%. These results translated to 156% earning on the strategic and operational portion, for a total, when combined with the financial portion, of 160%. See “Compensation Program Components” below for more details on the types of strategic and operational goals.

  28. 2024 LONG-TERM INCENTIVES

    2024 LONG-TERM INCENTIVES Equity grants for our NEOs in the fiscal year ended December 31, 2024 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 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

  29. 2024 LONG-TERM INCENTIVES

    | Hamilton Insurance Group, Ltd. | 2025 Proxy Statement | 44 |

  30. 2024 LONG-TERM INCENTIVES

    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, 2024, the Compensation and Personnel Committee selected two equally weighted PSU performance metrics: Return on Equity ("ROE") and Book Value per Share Growth ("BVSG") each measured on an absolute basis over a three-year performance period. These metrics replaced three-year annualized underwriting return on capital to better align with peer group market practices and being a public company. Performance achievement for the 2022-2024 PSU performance period was attained at 146.4% of target based on the achievement of three-year performance for underwriting return on capital.

  31. 2024 LONG-TERM INCENTIVES

    | Hamilton Insurance Group, Ltd. | 2025 Proxy Statement | 45 |

  32. 2024 COMPONENTS IN GENERAL

    2024 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, 2024, 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.

  33. 2024 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 |

  34. 2024 TARGET PAY MIX

    2024 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. Each compensation element is discussed in more detail below and set forth in more detail in the 2024 Summary Compensation Table and 2024 Grants of Plan-Based Awards table below

  35. 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 will not be funded, and the NEOs would not be entitled to any payout, regardless of his or her 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.

  36. ANNUAL CASH INCENTIVE PLAN

    | Hamilton Insurance Group, Ltd. | 2025 Proxy Statement | 48 |

  37. TARGET OPPORTUNITIES

    | NEO | 2023 Target Cash Incentive Opportunity (as a % of Base Salary) | 2024 Target Cash Incentive Opportunity (as a % of Base Salary) | | Giuseppina (Pina) Albo | 160 | 160 | | Craig Howie | 150 | 150 | | Megan Graves | 125 | 140 | | Adrian Daws | 125 | 140 | | Gemma Carreiro | 80 | 100 |

  38. FINANCIAL MEASURE (60%)

    FINANCIAL MEASURE (60%) For the fiscal year ended December 31, 2024, 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 and that considered the relevant risks and opportunities of the Company’s business but that does not fail to incentivize proper underwriting discipline. In particular, the Compensation and Personnel Committee reviewed our annual operating budget for the fiscal year ended December 31, 2024 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 95.2% for the fiscal year ended December 31, 2024 and set the threshold level of performance at 111.5%, and the maximum level of performance at 88.5%, a level that required exceptionally strong performance and represented a significant challenge.

  39. STRATEGIC AND OPERATIONAL MEASURES (40%)

    STRATEGIC AND OPERATIONAL MEASURES (40%) For the fiscal year ended December 31, 2024, 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 focused 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.

  40. BONUS POOL FUNDING

    BONUS POOL FUNDING The Compensation and Personnel Committee determined the bonus pool funding level based on the level of actual performance relative to the goals. To motivate performance and underscore the 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

  41. BONUS POOL FUNDING

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  42. BONUS POOL FUNDING

    level of performance. For performance between the threshold level and the target level, the funding level increases from 0% for 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%.

  43. 2024 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 | 111.5 | 95.2 | 88.5 | 91.3 | 163 | 98 | | Funding Percentage (as a % of target funding) | | 0 | 100 | 200 | | | | | Strategic and Operational Measures: | | | | | | | | | Strategic Growth | 20 | — | — | — | — | 200 | 40 | | Technology Enablement | 10 | — | — | — | — | 75 | 7.5 | | Magnet for Talent | 10 | — | — | — | — | 150 | 15 | | Aggregate Weighted Funding Percentage: | | | | | | | 160 |

  44. 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 bonus 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%.

  45. PAYOUT DETERMINATIONS

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  46. PAYOUT DETERMINATIONS

    The total payout under our annual cash incentive plan for each NEO for the fiscal year ended December 31, 2024 is reflected in the following table:

  47. PAYOUT DETERMINATIONS

    | NEO | 2024 Base Salary ($) | 2024 Target Cash Incentive Opportunity (as a % of Base Salary) | Target Incentive ($) | Bonus Pool Funding Plus Individual Performance (%) | Total 2024 Cash Incentive Payout Amount ($) | | Giuseppina (Pina) Albo | 1,300,000 | 160 | 2,080,000 | 175 | 3,640,000 | | Craig Howie | 640,000 | 150 | 960,000 | 174 | 1,675,000 | | Megan Graves | 635,000 | 140 | 889,000 | 160 | 1,422,000 | | Adrian Daws (1) | 491,684 | 140 | 682,644 | 162 | 1,108,188 | | Gemma Carreiro | 430,000 | 100 | 430,000 | 169 | 725,000 |

  48. PAYOUT DETERMINATIONS

    1.All amounts paid to Mr. Daws were paid in British pound sterling. The target and total cash incentive payout amounts for the fiscal year ended December 31, 2024, was converted using the exchange rate on February 25, 2025, the date when the Compensation and Personnel Committee approved the payout, of $1.2665 per GBP. For Mr. Daws base salary the 2024 average exchange rate of $1.2771 was used.

  49. 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 long-term underwriting performance goals are achieved and RSUs because they provide a retentive vehicle and alignment with long-term business performance.

  50. 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 base annual salary. The number of shares covered by the awards is calibrated by dividing the applicable target dollar amount by the per share fair market value of our shares as of the last day of the prior financial year ($19.03 for the grants made during the fiscal year ended December 31, 2024). In March 2024, 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 •Retention

  51. LONG-TERM INCENTIVE TARGET OPPORTUNITIES

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  52. LONG-TERM INCENTIVE TARGET OPPORTUNITIES

    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 modified the target incentive percentages for the fiscal year ended December 31, 2024 to better align each NEO’s incentive targets to the market as follows:

  53. LONG-TERM INCENTIVE TARGET OPPORTUNITIES

    | NEO | 2023 Target Long-term Incentive Opportunity (as a % of Base Salary) | 2024 Target Long-term Incentive Opportunity (as a % of Base Salary) | | Giuseppina (Pina) Albo | 250 | 275 | | Craig Howie | 200 | 230 | | Megan Graves | 150 | 160 | | Adrian Daws | 150 | 160 | | Gemma Carreiro | 80 | 100 |

  54. EQUITY VEHICLES AND 2024 MIX: PSUs AND RSUs

    EQUITY VEHICLES AND 2024 MIX: PSUs AND RSUs The mix of long-term incentives granted to the NEOs during the fiscal year ended December 31, 2024 is shown in the following table:

  55. EQUITY VEHICLES AND 2024 MIX: PSUs AND RSUs

    | Equity Vehicle | 2024 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 |

  56. EQUITY VEHICLES AND 2024 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.

  57. PSU PERFORMANCE METRIC

    PSU PERFORMANCE METRIC For the fiscal year ended December 31, 2024, the Compensation and Personnel Committee replaced three-year Annualized Underwriting Return on Capital (UROC) with two equally weighted PSU performance metrics: three-year average Return on Equity (ROE) and three-year annualized Book Value per Share Growth (BVSG). These metrics better 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.

  58. PSU PERFORMANCE METRIC

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  59. 2024 GRANTS OF PSUs AND RSUs

    2024 GRANTS OF PSUs AND RSUs The following table summarizes the grants to our NEOs:

  60. 2024 GRANTS OF PSUs AND RSUs

    | NEO | 2023 Base Salary ($) | 2024 Target Long-Term Incentive Opportunity (as a % of Base Salary) | Target Long-Term Incentive Value ($) | PSUs ($) | PSUs (#) | RSUs ($) | RSUs (#) | | Giuseppina (Pina) Albo | 1,300,000 | 275 | 3,575,000 | 1,787,500 | 123,276 | 1,787,500 | 123,276 | | Craig Howie | 600,000 | 230 | 1,380,000 | 690,000 | 47,586 | 690,000 | 47,586 | | Megan Graves | 590,000 | 160 | 944,000 | 472,000 | 32,552 | 472,000 | 32,552 | | Adrian Daws (1) | 445,284 | 160 | 712,454 | 356,227 | 25,245 | 356,227 | 25,245 | | Gemma Carreiro | 400,000 | 100 | 400,000 | 200,000 | 13,793 | 200,000 | 13,793 |

  61. 2024 GRANTS OF PSUs AND RSUs

    1.The base salary amount was converted to U.S. dollars using the 2023 average exchange rate, $1.2438 per GBP.

  62. 2022 PSUs WITH PERFORMANCE PERIOD COMPLETED AS OF FISCAL YEAR ENDED DECEMBER 31, 2024

    2022 PSUs WITH PERFORMANCE PERIOD COMPLETED AS OF FISCAL YEAR ENDED DECEMBER 31, 2024 In 2022, the Compensation and Personnel Committee granted PSUs with performance-based vesting requirements for the three-year performance period of 2022-2024 based on underwriting return on capital, which had the following performance curve:

  63. 2022 PSUs WITH PERFORMANCE PERIOD COMPLETED AS OF FISCAL YEAR ENDED DECEMBER 31, 2024

    | 2022 Performance Measure | Below Threshold (%) | Threshold (%) | Target (%) | Maximum (%) | Maximum or Above (%) | Actual (%) | | Underwriting Return on Capital | <(0.9) | (0.90) | 4.8 | 7.9 | >7.9 | 6.1 | | Payout Percentage of Target Shares | 0 | 0 | 100 | 200 | 200 | 146.4 |

  64. 2022 PSUs WITH PERFORMANCE PERIOD COMPLETED AS OF FISCAL YEAR ENDED DECEMBER 31, 2024

    The Compensation and Personnel Committee determined that the annualized underwriting return on capital for the 2022-2024 period was 6.1%, and correspondingly approved a performance payout at 146.4% 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:

  65. 2022 PSUs WITH PERFORMANCE PERIOD COMPLETED AS OF FISCAL YEAR ENDED DECEMBER 31, 2024

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  66. 2022 PSUs WITH PERFORMANCE PERIOD COMPLETED AS OF FISCAL YEAR ENDED DECEMBER 31, 2024

    | NEO | Earned PSUs (#) | | Giuseppina (Pina) Albo | 128,421 | | Craig Howie | 44,453 | | Megan Graves | 34,575 | | Adrian Daws | 23,373 | | Gemma Carreiro | 12,792 |

  67. 2022 PSUs WITH PERFORMANCE PERIOD COMPLETED AS OF FISCAL YEAR ENDED DECEMBER 31, 2024

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

  68. EXECUTIVE COMPENSATION COMPETITIVE MARKET INFORMATION

    EXECUTIVE COMPENSATION COMPETITIVE MARKET INFORMATION 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 takes into consideration 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 sets used previously, revised peer sets for the fiscal year ended December 31, 2023. Because our business includes reinsurance and specialty insurance, the peer sets include companies with businesses that encompass one or more of those segments. Also, because we have executive officers located in the United States, the United Kingdom and Bermuda, the compensation consultant developed peer sets for the positions in each of these geographic markets. For Bermuda, the number of prospective peer companies was low, so the peer set used for positions in Bermuda included both Bermuda and U.S. companies. 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 median range for similar positions at peer companies. Executive officers’ total compensation may deviate from the level referenced in order 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, 2023. Consistent with best practices for corporate governance, the Compensation and Personnel Committee intends to review our competitive market information annually.

  69. EXECUTIVE COMPENSATION COMPETITIVE MARKET INFORMATION

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  70. 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 programs generally, prepare reports that compare our compensation programs 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. Aon Solutions UK Limited ("Aon") served as the Compensation and Personnel Committee's independent compensation consultant from January until May 2024. During this portion of the fiscal year ended December 31, 2024, Aon: •Reviewed and advised the Compensation and Personnel Committee on compensation matters related to the Chief Executive Officer as well as our other executives •Prepared and presented on compensation benchmark analysis for each of Hamilton's executive team •Reviewed and advised on director compensation In June 2024, the Committee hired Mercer (US) LLC ("Mercer") as the independent compensation consultant. During this portion of the fiscal year ended December 31, 2024, Mercer: •Conducted stakeholder interviews and summarized key themes •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 executive benefits and perquisites

  71. 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 takes into consideration 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, revised peer sets for the fiscal year ended December 31, 2024. Because our business includes reinsurance and specialty insurance, the peer sets include companies with businesses that encompass one or more of those segments. Also, because we have executive officers located in the United States, the United Kingdom and Bermuda, the compensation consultant developed peer groups for the positions in each of these geographic markets. For Bermuda, the number of prospective peer companies was low, so the peer set used for positions in Bermuda included both Bermuda and U.S. companies. 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, 2024. Consistent with best practices for corporate governance, the Compensation and Personnel Committee intends to review 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.

  72. 2024 Compensation Benchmarking Peer Group

    2024 Compensation Benchmarking Peer Group For purposes of comparing our executive compensation against the competitive market, the Compensation and Personnel Committee reviews and considers the compensation levels and practices of a group of comparable companies. During the fiscal year ended December 31, 2024, the Compensation and Personnel Committee referenced the following compensation peer group for purposes of setting compensation and understanding the competitive market:

  73. 2024 Compensation Benchmarking Peer Group

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  74. 2024 Compensation Benchmarking Peer Group

    | Arch Capital Group Ltd. | Hiscox Ltd. | Palomar Holdings, Inc. | | Argo Group International Holdings, Inc.* | James River Group Holdings, Ltd. | RenaissanceRe Holdings Ltd. | | AXIS Capital Holdings Limited | Kinsale Capital Group, Inc. | RLI Corp. | | Beazley Group PLC | Lancashire Holdings Limited | Skyward Specialty Insurance Group, Inc. | | Everest Group, Ltd. | Markel Group Inc. | The Hanover Insurance Group, Inc. | | | | W.R. Berkley Corporation |

  75. 2024 Compensation Benchmarking Peer Group

    *Argo Group International Holdings, Inc was acquired by Brookfield Reinsurance in 2023. 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.

  76. 2025 Compensation Benchmarking Peer Group

    2025 Compensation Benchmarking Peer Group 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 don’t 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.

  77. 2025 Compensation Benchmarking Peer Group

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  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.

  79. TERMINATION AND CHANGE IN CONTROL PROVISIONS

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  80. TERMINATION AND CHANGE IN CONTROL PROVISIONS

    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 only triggered 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 the 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.

  81. 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.

  82. 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) and grants to any newly-hired or

  83. Equity Grant Timing

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  84. Equity Grant Timing

    promoted executives are typically made on the date of hire or promotion. We do not currently grant stock options or similar stock appreciation awards as part of our equity compensation program. Accordingly, during fiscal year ended December 31, 2024, (i) none of our NEOs were awarded stock options with an effective grant 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 were to be granted in the future, the Company would generally aim to avoid granting such options in anticipation of the release of material nonpublic information that is likely to result in changes to the price of our common stock.

  85. 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, 2024, 2023 and 2022.

  86. Summary Compensation Table

    | | | Salary | Bonus (1) | Stock Awards (2) | Non-Equity Incentive Plan Compensation (3) | All Other Compensation (4) | Total | | Name and Principal Position | Year | ($) | ($) | ($) | ($) | ($) | ($) | | Giuseppina (Pina) Albo | 2024 | 1,300,000 | — | 3,575,000 | 3,640,000 | 130,000 | 8,645,000 | | Chief Executive Officer | 2023 | 1,300,000 | 500,000 | 6,909,468 | 3,952,000 | 130,000 | 12,791,468 | | | 2022 | 1,300,000 | — | 2,599,992 | 1,625,000 | 148,999 | 5,673,991 | | Craig Howie | 2024 | 640,000 | — | 1,380,000 | 1,675,000 | 10,265 | 3,705,265 | | Chief Financial Officer | 2023 | 600,000 | 500,000 | 1,248,506 | 1,620,000 | 19,800 | 3,988,306 | | | 2022 | 600,000 | 600,000 | 899,988 | 640,000 | 18,300 | 2,758,288 | | Megan Graves | 2024 | 635,000 | — | 944,000 | 1,422,000 | 208,670 | 3,209,670 | | Chief Executive Officer of Hamilton Re | 2023 | 590,000 | 100,000 | 864,244 | 1,400,000 | 164,326 | 3,118,570 | | | 2022 | 560,000 | — | 700,008 | 525,000 | 123,541 | 1,908,549 | | Adrian Daws (5) | 2024 | 491,684 | — | 732,105 | 1,108,188 | 48,370 | 2,380,347 | | Chief Executive Officer of Hamilton International | 2023 | 447,768 | 102,418 | 609,292 | 1,078,820 | 43,222 | 2,281,520 | | | 2022 | 383,439 | — | 473,202 | 464,816 | 38,343 | 1,359,800 | | Gemma Carreiro (6) | 2024 | 430,000 | — | 400,000 | 725,000 | 151,650 | 1,706,650 | | General Counsel | 2023 | 400,000 | 500,000 | 351,636 | 580,000 | 187,205 | 2,018,841 | | (1) 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. The amount shown in the Bonus column for 2022 represents the second installment of an “initial hire grant” for Mr. Howie. | | | | | | | | | (2) 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 14 to our consolidated financial statements in our Annual Report on Form 10-K for the year ended December 31, 2024. The value of the PSU awards at the grant date assuming that the maximum level of performance conditions was achieved was as follows: $3,575,004 for Ms. Albo, $1,379,994 for Mr. Howie, $944,008 for Ms. Graves, $732,105 for Mr. Daws, and $399,997 for Ms. Carreiro. | | | | | | | | | (3) 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. | | | | | | | | | (4) The amounts shown in this column for the fiscal year ended December 31, 2024 include (i) contributions by the Company to retirement plans or cash payments in lieu of contributions as follows: $130,000 for Ms. Albo, $10,265 for Mr. Howie, $62,375 for Ms. Graves, $48,419 for Mr. Daws, and $42,250 for Ms. Carreiro; and (ii) payments of the employee’s share of Bermudian government payroll and social insurance taxes: $146,295 for Ms. Graves, and $109,400 for Ms. Carreiro. | | | | | | | | | (5) The U.S. dollar amounts in the table above for Mr. Daws were converted from British pound sterling (“GBP”) using the 2024 average exchange rate, $1.2771 per GBP, for his salary and all other compensation and the exchange rate on February 25, 2025, $1.2665 per GBP, for his 2024 non-equity incentive plan compensation. The amounts reflected for base salary represent the salary at year end. | | | | | | | | | (6) Ms. Carreiro was not a NEO for the fiscal year ended December 31, 2022 and therefore in accordance with SEC regulations, only compensation information for the fiscal years ending December 31, 2023 and December 31, 2024 are included in the Summary Compensation Table. | | | | | | | |

  87. Summary Compensation Table

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  88. Grants of Plan-Based Awards in 2024

    Grants of Plan-Based Awards in 2024 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, 2024.

  89. Grants of Plan-Based Awards in 2024

    | | | 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 | 03/05/2024 | | | | | | | 123,276 | 1,787,502 | | | 03/05/2024 | | | | 0 | 123,276 | 246,552 | | 1,787,502 | | Craig Howie | | 0 | 960,000 | 1,920,000 | | | | | | | | 03/05/2024 | | | | | | | 47,586 | 689,997 | | | 03/05/2024 | | | | 0 | 47,586 | 95,172 | | 689,997 | | Megan Graves | | 0 | 889,000 | 1,778,000 | | | | | | | | 03/05/2024 | | | | | | | 32,552 | 472,004 | | | 03/05/2024 | | | | 0 | 32,552 | 65,104 | | 472,004 | | Adrian Daws (5) | | 0 | 688,357 | 1,376,714 | | | | | | | | 03/05/2024 | | | | | | | 25,245 | 366,053 | | | 03/05/2024 | | | | 0 | 25,245 | 50,490 | | 366,053 | | Gemma Carreiro | | 0 | 430,000 | 860,000 | | | | | | | | 03/05/2024 | | | | | | | 13,793 | 199,999 | | | 03/05/2024 | | | | 0 | 13,793 | 27,586 | | 199,999 | | (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, 2024. 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 2024 annual cash incentive plan results 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 on March 5, 2024 reflect the number of shares that may be realized under the PSUs granted to our NEOs in 2024 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” and One Time Recognition Grant for 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 2024. The RSUs granted in March 2024 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 14 to our consolidated financial statements in our Annual Report on Form 10-K for the year ended December 31, 2024. 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 were converted from British pound sterling (“GBP”) using the 2024 average exchange rate, $1.2771 per GBP for his non-equity incentive awards | | | | | | | | | |

  90. Grants of Plan-Based Awards in 2024

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  91. Outstanding Equity Awards at Fiscal Year Ended December 31, 2024

    Outstanding Equity Awards at Fiscal Year Ended December 31, 2024 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, 2024.

  92. Outstanding Equity Awards at Fiscal Year Ended December 31, 2024

    | | | | 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 | 02/23/2022(5) | 29,240 | 556,437 | | | | | | 03/10/2023(6) | 78,960 | 1,502,609 | | | | | | 11/10/2023(7) | 116,667 | 2,220,173 | | | | | | 03/05/2024(8) | 123,276 | 2,345,942 | | | | | PSU | 02/23/2022(9) | | | 87,719 | 1,669,293 | | | | 03/10/2023(10) | | | 118,440 | 2,253,913 | | | | 11/10/2023(11) | | | 250,000 | 4,757,500 | | | | 03/05/2024(12) | | | 123,276 | 2,345,942 | | | VAP | 12/01/2020(13) | 151,566 | 2,884,301 | | | | Craig Howie | RSU | 02/23/2022(5) | 10,121 | 192,603 | | | | | | 03/10/2023(6) | 29,155 | 554,820 | | | | | | 03/05/2024(8) | 47,586 | 905,562 | | | | | PSU | 02/23/2022(9) | | | 30,364 | 577,827 | | | | 03/10/2023(10) | | | 43,732 | 832,220 | | | | 03/05/2024(12) | | | 47,586 | 905,562 | | | VAP | 07/01/2021(13) | 50,522 | 961,434 | | | | Megan Graves | RSU | 02/23/2022(5) | 7,872 | 149,804 | | | | | | 03/10/2023(6) | 20,408 | 388,364 | | | | | | 03/05/2024(8) | 32,552 | 619,465 | | | | | PSU | 02/23/2022(9) | | | 23,617 | 449,432 | | | | 03/10/2023(10) | | | 30,612 | 582,546 | | | | 03/05/2024(12) | | | 32,552 | 619,465 | | | VAP | 12/01/2020(13) | 33,681 | 640,949 | | | | Adrian Daws | RSU | 02/23/2022(5) | 5,322 | 101,278 | | | | | | 03/10/2023(6) | 13,625 | 259,284 | | | | | | 03/05/2024(8) | 25,245 | 480,412 | | | | | PSU | 02/23/2022(9) | | | 15,965 | 303,814 | | | | 03/10/2023(10) | | | 20,437 | 388,916 | | | | 03/05/2024(12) | | | 25,245 | 480,412 | | | VAP | 12/01/2020(13) | 33,681 | 640,949 | | | | Gemma Carreiro | RSU | 02/23/2022(5) | 2,912 | 55,415 | | | | | | 03/10/2023(6) | 7,482 | 142,382 | | | | | | 03/05/2024(8) | 13,793 | 262,481 | | | | | PSU | 02/23/2022(9) | | | 8,738 | 166,284 | | | | 03/10/2023(10) | | | 11,224 | 213,593 | | | | 03/05/2024(12) | | | 13,793 | 262,481 | | | VAP | 12/01/2020(13) | 29,471 | 560,833 | | |

  93. Outstanding Equity Awards at Fiscal Year Ended December 31, 2024

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  94. Outstanding Equity Awards at Fiscal Year Ended December 31, 2024

    | (1) Amounts disclosed in this column reflect the number of unvested RSUs granted that had not vested as of December 31, 2024. 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, 2024, $19.03, 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, 2024. 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, 2024, $19.03, 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 February 23, 2022 vest in three equal annual installments on January 1 of each of 2023, 2024, and 2025, respectively, subject to the NEO’s continued service through each vesting date. | | (6) 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. | | (7) 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. | | (8) 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. | | (9) The PSUs granted to our NEOs on February 23, 2022 are earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2024. The amounts reflect achievement at target as of December 31, 2024. | | (10) 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 achievement at target as of December 31, 2024 (which reflects the probable achievement level of the applicable performance conditions). | | (11) 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%. | | (12) 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 target as of December 31, 2024 (which reflects the probable achievement level of the applicable performance conditions). | | (13) The VAP units granted to our NEOs vest, in the case of a trigger event (initial public offering, change in control, or major sale), 50% on the one-year anniversary of the trigger event and 50% one year thereafter. As the result of our initial public offering, 50% of the RSUs earned from the VAP units vest on November 9, 2024 and 50% on November 9, 2025. |

  95. Outstanding Equity Awards at Fiscal Year Ended December 31, 2024

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  96. Stock Vested in Fiscal Year Ended December 31, 2024

    Stock Vested in Fiscal Year Ended December 31, 2024 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, 2024.

  97. Stock Vested in Fiscal Year Ended December 31, 2024

    | | Stock Awards | | | | Number of Shares | Value Realized | | | Acquired on Vesting (1) | on Vesting (2) | | Name | (#) | ($) | | Giuseppina (Pina) Albo | 268,301 | 4,443,066 | | Craig Howie | 75,220 | 1,268,527 | | Megan Graves | 70,734 | 1,153,464 | | Adrian Daws | 55,237 | 921,784 | | Gemma Carreiro | 41,592 | 705,793 | | (1) The amounts shown in this column represent the number of RSUs that vested and the 2021-2023 PSUs that were earned for each NEO during the fiscal year ended December 31, 2024. | | | | (2) The amounts shown in this column reflect the value realized upon vesting of the RSUs and the earning of 2021-2023 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. | | |

  98. Stock Vested in Fiscal Year Ended December 31, 2024

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  99. 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.

  100. 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.

  101. 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, 2024, 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.

  102. Pay Versus Performance Table and Disclosures

    Pay Versus Performance Table and Disclosures In accordance with rules adopted by the Securities and Exchange Commission 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-PEOs 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.

  103. 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-PEOs(1)($) | Average Compensation Actually Paid to Non-PEOs(1),(2),(3) ($) | Value of Initial Fixed $100 Investment based on:(4) | | Net Income ($ Millions) | Combined Ratio (%)(5) | | | | | | | TSR ($) | Peer Group TSR ($) | | | | 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% |

  104. Pay Versus Performance Table and Disclosures

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

  105. Pay Versus Performance Table and Disclosures

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

  106. 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. 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:

  107. Pay Versus Performance Table and Disclosures

    | | Fiscal 2023 | | Fiscal 2024 | | | | PEO | Average Non-PEO | PEO | Average Non-PEO | | Total Reported in Summary Compensation Table | 12,791,468 | 2,851,809 | 8,645,000 | 2,751,683 | | Less, value of awards reported in Summary Compensation Table | (6,909,468) | (768,419) | (3,575,000) | (865,090) | | Plus, year-end value of awards granted in fiscal year that are unvested and outstanding at the end of the fiscal year | 8,327,680 | 1,188,581 | 7,037,827 | 1,700,939 | | Plus, change in fair value of prior year awards that are unvested and outstanding at end of fiscal year | 916,851 | 203,399 | 4,684,657 | 768,556 | | Plus, fair value of awards granted in fiscal year and that vested in this fiscal year | 0 | 0 | 0 | 0 | | Plus, change in fair value of prior year awards that vested in this fiscal year | 459,467 | 13,784 | 431,966 | 104,990 | | Less, fair value of prior year awards that failed to vest this fiscal year | 0 | 0 | 0 | 0 | | Total Adjustments | 9,703,998 | 1,405,764 | 8,579,450 | 1,709,397 | | Compensation Actually Paid | 15,585,998 | 3,489,754 | 17,224,450 | 4,461,080 |

  108. 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, 2024. The comparison assumes $100 was invested for the period starting November 10, 2023 and ending on December 31, 2024 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 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-PEOs in 2024. 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

  109. Pay Versus Performance Table and Disclosures

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  110. Pay Versus Performance Table and Disclosures

    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

  111. Relationship Between PEO and Non-PEO Compensation Actually Paid and Total Shareholder Return (“TSR”)

    Relationship Between PEO and Non-PEO Compensation Actually Paid and Total Shareholder Return (“TSR”) 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 TSR over the two most recently completed fiscal years and the S&P 500 Property & Casualty Insurance Index TSR over the same period.

  112. Relationship Between PEO and Non-PEO Compensation Actually Paid and Total Shareholder Return (“TSR”)

    | Hamilton Insurance Group, Ltd. | 2025 Proxy Statement | 78 |

  113. 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 two most recently completed fiscal years.

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

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  115. 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 two most recently completed fiscal years.

  116. 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, 2024: •The median employee's annual total compensation was $153,415. •The annual total compensation of our CEO, Ms. Albo, was $8,645,000. •Based on this information, the ratio of the annual total compensation of our CEO to that of the median employee was 56.35 to one. We determined that as of December 31, 2024, our employee population consisted of 603 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 foreign exchange rates as of December 31, 2024. 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.

  117. CEO Pay Ratio

    | Hamilton Insurance Group, Ltd. | 2025 Proxy Statement | 81 |

  118. 2024 Director Compensation

    2024 Director Compensation Our Board of Directors approved a new compensation program for our non-employee directors, effective January 1, 2024, to better align with the market for public companies. Non-employee members of our Board of Directors receive the following compensation for service on our Board of Directors: •Annual compensation package of $250,000, $150,000 of which will be in the form of an RSU granted on the date of the annual general meeting that cliff vests on the earlier of one-year or the date of the subsequent annual general meeting and $100,000 of which will be paid in cash on a quarterly, pro rata basis. Non-employee directors may elect to defer the receipt of 50% or 100% of their RSUs •Additional compensation for the chair of the Board of Directors of $175,000, which will be paid in cash, for total chair annual compensation of $425,000, •Additional compensation for the chair of the Audit Committee of $50,000, which will be paid in cash •Additional compensation for the chair of the Compensation and Personnel Committee of $25,000, which will be paid in cash •Additional compensation for the chair of other committees of $20,000, which will be paid in cash •Additional compensation for directors who serve on the board of directors of an operating subsidiary of the Company of $20,000, which will be paid in either cash or Company shares, at the director’s election In addition, in connection with the transition of the timing of annual equity awards to the date of the Annual General Meeting, for the period from January 1, 2024 (or, if later, the date a director was appointed to the Board of Directors in 2024) until the date of the Company’s 2024 Annual General Meeting, a one-time cash payment equal to a pro-rated amount of the annual value of the equity portion of the annual compensation package was also awarded. Non-employee members of our board who do not serve as the chair of a committee will not receive fees for service on the separate committees of our Board of Directors. We also reimburse our directors for reasonable and necessary out-of-pocket expenses incurred in attending board and committee meetings or performing other services for us in their capacities as directors. To strengthen the alignment of interests among our non-employee directors and our Shareholders and to demonstrate sound corporate governance, our non-employee directors are subject to share ownership guidelines. These guidelines provide that within five years of being appointed, non-employee directors must hold a minimum of five times the value of their annual retainer fee (excluding any portion of the annual compensation package paid in Company shares and committee chair fees or fees for serving on the board of directors of an operating subsidiary of the Company) in Company shares.

  119. 2024 Director Compensation

    | Hamilton Insurance Group, Ltd. | 2025 Proxy Statement | 82 |

  120. Director Summary Compensation Table

    | | Fees Earned or Paid in Cash (1) | Stock Awards (2) | Total | | Name | ($) | ($) | ($) | | William C. Freda | 172,500 | 150,000 | 322,500 | | David Brown | 357,500 | 150,000 | 507,500 | | Stephen Pacala | 174,167 | 150,000 | 324,167 | | Pauline Richards | 75,000 | | 75,000 | | Russ Fradin | 125,000 | | 125,000 | | Marvin Pestcoe | 202,500 | 150,000 | 352,500 | | Barclay Simmons | 162,500 | 150,000 | 312,500 | | John Gauthier (3) | 177,083 | 162,500 | 339,583 | | Henna Karna (3) | 162,500 | 162,500 | 325,000 | | Terri Vaughan (4) | 120,833 | 150,000 | 270,833 | | Neil Patterson (4) | 161,310 | 150,000 | 311,310 | | Brad Cooper (5) | — | — | — | | Hawes Bostic (5) | — | — | — | | (1) Annual director compensation for the fiscal year ended December 31, 2024 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 for them reflects the amount of cash compensation received by each non-employee director. Additional compensation for the chair of the Board of Directors 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 June 2024, and will vest after the Annual General Meeting. | | | | | (3) Mr. Gauthier and Ms. Karna were appointed to the Board on October 24, 2023. They each received an additional fully vested grant of Class B Common shares with a grant date value of $12,500 in the first quarter of 2024 for their two months of Board service in 2023. | | | | | (4) Ms. Vaughan and Mr. Patterson were appointed to the Board effective as of March 11, 2024. Their annual fees are prorated based on their respective service periods. | | | | | (5) Mr. Cooper and Mr. Bostic serve on the Board without compensation. | | | |