hg-20260324

UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
WASHINGTON, D.C. 20549
___________________________________
SCHEDULE 14A
Proxy Statement Pursuant to Section 14(a) of
the Securities Exchange Act of 1934

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HAMILTON INSURANCE GROUP, LTD.

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(Name of Registrant as Specified In Its Charter)

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Notice of 2026 Annual General
Meeting of Shareholders

On behalf of the Hamilton Insurance Group, Ltd. Board of Directors, (the "Board of Directors" or "Board") you are cordially invited to attend the Hamilton 2026 Annual General Meeting of Shareholders (the “Annual Meeting" or “Annual General Meeting”).

Meeting Details



Date and Time	Location	Record Date
May 5, 2026 at 9:00 A.M. Eastern Time ("ET")	Live via the Internet at www.virtualshareholdermeeting.com/HG2026	Shareholders of record as of the close of business on March 17, 2026 are entitled to vote at the Annual Meeting

How To Vote


Method	Details	Vote must be received or submitted by:
By Phone	1-800-690-6903	11:59 p.m. ET, May 4, 2026
Online Before the Meeting	www.proxyvote.com	11:59 p.m. ET, May 4, 2026
By Mail	Return your completed proxy card in the prepaid envelope	11:59 p.m. ET, May 4, 2026
Online During the Meeting	www.virtualshareholdermeeting.com/HG2026	Before the polls close during the Annual Meeting

Matters to Be Voted On


1			To elect 11 Class B directors to serve until the 2027 Annual General Meeting of Shareholders or until their successors are duly elected and qualified
2			To approve, on a non-binding advisory basis, the compensation paid to our named executive officers
3			To appoint Ernst & Young Ltd. to act as our independent registered public accounting firm for the fiscal year ending December 31, 2026, and to authorize the Board, acting through the Audit Committee, to set the fees for the independent registered public accounting firm

We may also transact any other business as may properly come before the meeting. As of the date of this proxy statement, we are not aware of any business to be presented for consideration other than the matters described above.

Proxies

The Board of Directors is soliciting proxies to be voted at the Annual Meeting on May 5, 2026, and at any postponed or reconvened meeting. Shareholders of record are being mailed, sent or given, on or about March 24, 2026, a Notice of Internet Availability of Proxy Materials providing instructions on how to access the Proxy Materials on the Internet.

Accessing the 2026 Annual General Meeting

Your vote is important—we value input from all of our shareholders.

Please take time to review the accompanying proxy statement, which includes important details about the proposals to be considered at the Annual General Meeting.

To join the meeting and vote, you will need the 16-digit control number found on your Notice of Internet Availability of Proxy Materials, your proxy card, or any voting instruction form included with these materials.

This year’s Annual General Meeting will be held in a virtual format, allowing shareholders to attend, vote, and submit questions online. We believe this approach enhances accessibility and encourages meaningful engagement with management, no matter where you are located. You are encouraged to participate virtually and vote your shares in advance by proxy.

For more information on voting and participating in the virtual meeting, please refer to the “Voting and Meeting Information” section in the proxy statement.

By order of the Board,

Gemma Carreiro
General Counsel & Secretary
March 24, 2026


			Important Notice Regarding the Availability of Proxy Materials to be held virtually via the Internet on May 5, 2026. Our 2026 proxy statement as well as our 2025 Annual Report are available free of charge in the investors section of our website at www.hamiltongroup.com.

Table of Contents


Proxy Statement Summary			1
Annual General Meeting Information			1
Proposals			1
Corporate Governance			5
PROPOSAL ONE: Election of Class B Directors			5
Board Composition			12
Skills, Qualifications and Experience of Directors			14
Board and Committee Evaluations			17
Certain Relationships and Related Party Transactions			17
Board Committees			20
Meetings of the Board and its Committees			22
Meetings of Non-Management Directors			22
Compensation and Personnel Committee Interlocks and Insider Participation			23
Board Leadership Structure			23
Consideration of Director Nominees			23
Board Oversight of Risk and Risk Management			24
Code of Conduct and Corporate Governance Framework			25
In Good Company: How We Work and What We Stand For			25
Governance‑Driven Long-Term Value Creation			26
Human Capital Management			28
Shareholder Engagement			29
Security Ownership of Certain Beneficial Owners and Management			31
Executive Officers			34
Compensation			38
PROPOSAL TWO: Non-Binding Advisory Vote on Fiscal 2025 Compensation Paid to our Named Executive Officers			38
Compensation Discussion and Analysis			40
Compensation and Personnel Committee Report			63
Executive Compensation Tables			64
Employment and Other Agreements with Named Executive Officers			66
Long-Term Equity Compensation			68
Annual Incentive Plan			68
Additional Benefits			68
Pension Benefits			71
Nonqualified Defined Contribution and Other Nonqualified Deferred Compensation Plans			71
Potential Payments Upon Termination or Change in Control			71
Equity Compensation Plan Information Table			75
Pay Versus Performance Table and Disclosures			76
CEO Pay Ratio			80
2025 Director Compensation			81
Audit Matters			83
PROPOSAL THREE: Appointment of Independent Auditors			83
Audit Committee Report			84
Principal Accountant Fees and Services			85
Shareholder Proposals for 2027 Annual General Meeting			86
Shareholder Proposals for Inclusion in 2027 Proxy Statement			86
Shareholder Proposals to be Introduced at the 2027 Annual General Meeting			86
Voting and Meeting Information			87
Other Matters			91
Appendix 1 - Non-GAAP Financial Measures			93
Non-GAAP Financial Measures Reconciliation			93
Operating Ratios			94
Appendix 2: Class A Proxy Card			95
Appendix 3: Class B Proxy Card			98

Cautionary Note Regarding Forward-Looking Statements

This proxy statement contains forward-looking statements within the meaning of the U.S. Private Securities Litigation Reform Act of 1995. Forward-looking statements can be identified by the use of terms such as “believes,” “expects,” “may,” “will,” “target,” “should,” “could,” “would,” “seeks,” “intends,” “plans,” “contemplates,” “estimates,” or “anticipates,” or similar expressions which concern our strategy, plans, projections or intentions. These forward-looking statements appear throughout this proxy statement and address such matters such as our industry, growth strategy, market position, future operations, margins, profitability, capital expenditures, liquidity and capital resources, corporate governance practices, risk management, shareholder engagement, executive and director compensation programs, and equity compensation utilization. By their nature, forward-looking statements: speak only as of the date they are made; are not statements of historical fact or guarantees of future performance; and are subject to risks, uncertainties, assumptions, and changes in circumstances that are difficult to predict or quantify. Although we believe our expectations and projections are reasonable, actual results may differ materially.

Factors that can cause results to differ materially include those described under “Special Note Regarding Forward-Looking Statements” in Hamilton's Annual Report on Form 10-K ("Annual Report") filed with the Securities and Exchange Commission ("SEC") and available on our website, as well as other risks and uncertainties. You should evaluate all forward-looking statements in the context of these risks and uncertainties.

We cannot assure you that we will achieve the results or developments we expect or, even if realized, that they will have the anticipated effects. All forward-looking statements in this proxy statement apply only as of its date and are expressly qualified in their entirety by this cautionary note. We undertake no obligation to publicly update or revise any forward-looking statements to reflect subsequent events or circumstances.

When used in this proxy statement, unless otherwise mentioned or unless the context indicates otherwise, the terms "we", "us", "our", the "Company", the "Group" and "Hamilton" refer to Hamilton Insurance Group, Ltd. and its consolidated subsidiaries.

Proxy Statement Summary

Annual General Meeting Information

•Date and Time: May 5, 2026 at 9am ET

•Virtual Meeting: www.virtualshareholdermeeting.com/HG2026

•Record Date: March 17, 2026

Proposals

This proxy statement summary highlights information regarding Hamilton and certain information included elsewhere in this proxy statement. It is not a substitute for the full proxy statement, and we encourage you to read the entire proxy statement before voting. You should also review our Annual Report for detailed information regarding our financial and operating performance for the year ended December 31, 2025, including the audited financial statements and related notes.

Proposal

Board Recommendation

Vote Required to Adopt Proposal

Page Ref.

Election of Class B directors

FOR

each Nominee

The affirmative vote of a plurality of the votes cast by holders of Class B common shares present in person or by proxy at the Annual General Meeting, provided that holders of more than 50% of such shares are present in person or by proxy to constitute a quorum. Broker non-votes and abstentions will not be considered votes cast and will have no effect on the outcome.

Non-binding advisory vote on fiscal year 2025 compensation paid to our named executive officers

FOR

The affirmative vote of a majority of the votes cast by holders of common shares present in person or by proxy at the Annual General Meeting and entitled to vote thereon. Broker non-votes and abstentions will not be considered votes cast and will have no effect on the outcome.

Appointment of Ernst & Young Ltd. to act as our independent registered public accounting firm for the fiscal year ending December 31, 2026 and to authorize the Board, acting through the Audit Committee, to set the fees for the independent registered public accounting firm

FOR

The affirmative vote of a majority of the votes cast by holders of common shares present in person or by proxy at the Annual General Meeting and entitled to vote thereon. Abstentions will not be considered votes cast and will have no effect on the outcome.

We may also transact any other business that may properly come before the meeting. As of the date of this proxy statement, we are not aware of any business to be presented for consideration other than the matters described above.


Hamilton Insurance Group, Ltd.			2026 Proxy Statement						1

Company Overview

We are a global specialty insurance and reinsurance company founded in Bermuda in 2013. We harness multiple drivers to create shareholder value. These include diverse underwriting operations supported by proprietary technology and a team of over 600 full-time employees, a strong balance sheet, and a unique investment management relationship with Two Sigma (see "Certain Relationships and Related Party Transactions" for additional details on our arrangement with Two Sigma ). We operate globally, with underwriting operations in London, Ireland, Bermuda, and the United States.

We are led by an entrepreneurial and experienced management team that has grown premiums written from $571 million for the year ended November 30, 2018, to $2.9 billion for the fiscal year ended December 31, 2025, while also reducing our combined ratio significantly. The combined effects of organic premium growth, strategic acquisition, new market developments and continuous platform cost optimization leave us well positioned to capitalize on the favorable market conditions across the lines of business written by our established and scaled underwriting platforms.

2025 Company Financial Performance


	FINANCIAL PERFORMANCE
Net income attributable to common shareholders of $576.7 million	Gross premiums written of $2.9 billion	Underwriting income(1) of $148.8 million
Return on average equity ("ROE") of 22.4%	Net premiums earned of $2.1 billion	Combined ratio of 92.9 %

In Good Company: Our People & Citizenship

At Hamilton, our success begins with our people. We foster an inclusive, entrepreneurial, and collaborative culture that enables our colleagues to deliver on our strategic priorities and support our commitment to disciplined underwriting. This culture — reflected in our corporate tagline, "In good company." — helps us attract, engage, and retain top talent through our “Magnet for Talent” business imperative and our ongoing investment in colleague development and engagement.

We are equally committed to being responsible corporate citizens. As underwriters and as global participants in the communities where we live and work, we strive to apply our business strengths to make a positive and lasting impact. Hamilton seeks to operate in a manner that considers our effect on society today and for future generations, and we actively support initiatives that promote community well-being and responsible business practices.

For more information on our people, culture, and corporate citizenship efforts, please see Corporate Governance – Human Capital Management.

1.Underwriting income is a non-GAAP financial measure. A reconciliation of non-GAAP financial measures is included in “Appendix 1.”


Hamilton Insurance Group, Ltd.			2026 Proxy Statement						2

Executive Compensation Highlights

Our executive compensation program is guided by our overarching philosophy of only paying for demonstrable performance. Key Features of our compensation program include:

•Pay-for-Performance: Compensation is primarily performance-based and rewards executives for achieving financial, operational, and strategic goals.

•Competitive and Reasonable: Designed to attract, motivate, and retain top executive talent while remaining aligned with market practices.

•Balanced Approach: Combines short-term and long-term incentives to drive sustainable results.

•Strong Governance: Maintains sound governance standards consistent with our compensation policies and practices.


What We Do			What We Don't Do
Pay for Performance			No Perks
Independent Compensation Committee			No Excise Tax Gross-Ups
Independent Compensation Consultant			No Hedging or Pledging of Company Shares
Clawback Policy			No Guaranteed Performance Bonuses(1)
Share Ownership Guidelines			No Dividend Equivalents on Unvested Performance Awards(2)
Caps on Annual Bonuses and Equity Grants
Double Trigger Change-in-Control Severance and Acceleration
Peer Data
Multi-year Vesting and Earn-out Requirements
Risk Mitigation

For more information on executive compensation, see "Compensation Discussion and Analysis."

1. We do not provide guaranteed performance bonuses to our named executive officers at any minimum levels of payment under our annual cash incentive plan. For more information see "Compensation Discussion and Analysis" below.

2. We do not pay dividends or dividend equivalents on performance-based awards unless and until the performance awards are earned and vested. For more information see "Compensation Discussion and Analysis" below.


Hamilton Insurance Group, Ltd.			2026 Proxy Statement						3

Corporate Governance Highlights

Corporate governance is a key area of focus for our Board. Our current governance practices include the below, a number of which are discussed in further detail throughout this proxy statement:

•Regular and proactive shareholder engagement

•Annual say-on-pay vote

•Our Board is composed of a majority of independent directors and the Audit, Compensation and Personnel, and Nominating and Corporate Governance Committees are composed of only independent directors

•None of our directors serve on the board of directors of more than four other publicly-held corporations

•There is no shareholder rights plan ("poison pill")

•All Class B shareholders have the right to vote on the election of the Class B directors on an annual basis

•Independent Chairman

•Stock ownership guidelines for executive officers and directors

•Our Board and each committee holds quarterly executive sessions without management present as well as an annual self-evaluation process

•Our Board provides oversight of key risks that impact the Company's ability to achieve its strategy

•Technology Committee provides oversight of technology strategy and cybersecurity risk management

•Robust clawback policy

•Our Board regularly reviews committee charters and key governance policies

•Our Board is engaged in an ongoing refreshment process to ensure coverage of the key skill-sets identified by the Board

General Information, Questions and Answers

Please see “Voting and Meeting Information” and “Shareholder Proposals for 2027 Annual General Meeting” for important information about the 2026 Annual Meeting, proxy materials, voting, and the deadlines to submit shareholder proposals and director nominees for the 2027 annual general meeting and other important information.


Hamilton Insurance Group, Ltd.			2026 Proxy Statement						4

Corporate Governance

PROPOSAL ONE:
Election of Class B Directors

Our business and affairs are managed under the direction of our Board. Our bye-laws provide that our Board consist of not less than eleven (11) directors or more than fifteen (15) directors as the Board may determine from time to time. The Board presently consists of thirteen (13) directors, including eleven (11) Class B directors and two (2) Shareholder Directors.

Under the Shareholders Agreement, dated November 14, 2023 (the “Shareholders Agreement”), four significant shareholders (each holding at least 5% of our issued and outstanding common shares as of such date) initially held the right to appoint one director each to our Board (each, a “Shareholder Director”), subject to maintaining certain ownership thresholds. One of these shareholders subsequently sold its shares back to the Company and no longer meets the required ownership level, and therefore has lost its appointment right. Of the three remaining shareholders that continue to hold such rights, two have appointed a Shareholder Director, while one has not yet exercised its right to do so but continues to retain that right. Additional details regarding the Shareholders Agreement are provided under “Board Composition” below.

At the Annual General Meeting, eleven (11) Class B directors will be elected by the holders of our Class B common shares (“Class B directors” ) to serve until the next annual general meeting of shareholders or until their successors are duly elected and qualified. These directors will join the two (2) Shareholder Directors appointed in accordance with the Shareholders Agreement and the Company’s bye-laws. Following the Annual General Meeting, the Board will continue to consist of thirteen (13) directors: eleven (11) Class B directors and two (2) Shareholder Directors. As further described below, one additional shareholder continues to retain the right, under the Shareholders Agreement, to appoint a Shareholder Director, although it has not yet exercised that right.

Recommendation




			The Board recommends that shareholders vote their shares "FOR" the election of each of the eleven (11) Class B directors nominated by our Board and named in this proxy statement as a director to serve until the next annual general meeting or until his or her successor is elected and qualified

Vote Required

The election of Class B directors will be determined by a plurality of the votes cast by holders of Class B common shares present in person or represented by proxy at the Annual General Meeting, provided that holders of more than 50% of the Class B common shares entitled to vote are present in person or by proxy to constitute a quorum. Voting is subject to the limitations set forth in the Company’s bye-laws. Broker non-votes and abstentions will not be considered votes cast and will have no effect on the outcome of this proposal.


Hamilton Insurance Group, Ltd.			2026 Proxy Statement						5

Class B Director Nominees

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

Name

Age

Committees

Position

Since

David A. Brown

Compensation and Personnel

Independent Director

2013

Giuseppina (Pina) Albo

CEO and Director

2018

John J. Gauthier

Compensation and Personnel, Nominating and Governance and Investment

Independent Director

2023

Karen Ann Green

Audit, Underwriting and Risk and Compensation and Personnel

Independent Director

2025

Anu (Henna) Karna

Nominating and Governance and Technology

Independent Director

2023

Neil Patterson

Audit, Nominating and Governance and Technology

Independent Director

2024

Marvin Pestcoe

Underwriting and Risk, Investment and Technology

Independent Director

2020

David Priebe

Audit, Underwriting and Risk and Technology

Independent Director

2025

Everard Barclay Simmons

Audit, Investment and Technology

Independent Director

2023

Therese Vaughan

Compensation and Personnel, Nominating and Governance and Underwriting and Risk

Independent Director

2024

Peter W. Wilson

Proposed to be on Underwriting and Risk, Nominating and Governance and Technology

Independent Director

First-time Nominee


Hamilton Insurance Group, Ltd.			2026 Proxy Statement						6

Class B Director Nominee Biographies


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


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


Hamilton Insurance Group, Ltd.			2026 Proxy Statement						7


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


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


Hamilton Insurance Group, Ltd.			2026 Proxy Statement						8


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


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


Hamilton Insurance Group, Ltd.			2026 Proxy Statement						9


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


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


Hamilton Insurance Group, Ltd.			2026 Proxy Statement						10


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


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.


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



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


Hamilton Insurance Group, Ltd.			2026 Proxy Statement						11

Board Composition

We believe it is essential to have a qualified group of directors with an appropriate mix of skills, experience and attributes to oversee our business. Accordingly, the size and composition of the Board are reviewed periodically to balance the need for diverse perspectives and expertise, with the practical considerations of efficient corporate governance.

In addition to the foregoing, we entered into the Shareholders Agreement with certain shareholders who, together with their affiliates, owned at least 5% of our issued and outstanding common shares as of that date. Those shareholders included: the Magnitude Investor (collectively being, Magnitude Master Fund, a sub trust of the Magnitude Master Series Trust, Magnitude Institutional, Ltd., Magnitude Partners Master Fund, L.P., and Magnitude Insurance Master Fund, LLC), Sango Holdings (being Sango Hoken Holdings, LLC), Hopkins Holdings (being Hopkins Holdings, LLC) and the Blackstone Investor Group (collectively comprising BSOF Master Fund L.P. and BSOF Master Fund II L.P.), including any permitted transferee of any of the foregoing. Under the Shareholders Agreement, each such shareholder had the right to appoint one Shareholder Director, subject to the maintenance of certain ownership thresholds. Following the sale of its holdings in Hamilton back to the Company in 2024, the Blackstone Investor Group no longer meets the ownership threshold and its appointment right has terminated. The remaining Class B directors are elected by the holders of our Class B common shares for an annual term expiring at each annual general meeting or until their successors are elected or appointed or their office is otherwise vacated.

Currently, the Shareholder Directors are Bradley Cooper and Marc Roston (who succeeded H. Hawes Bostic III as the Magnitude Investor director in February 2026) and the Class B directors are David A. Brown, Giuseppina (Pina) Albo, John J. Gauthier, Karen Ann Green, Anu (Henna) Karna, Stephen W. Pacala, David Priebe, Neil Patterson, Marvin Pestcoe, Everard Barclay Simmons and Therese Vaughan. Sango Holdings has retained its right to appoint one director pursuant to the terms of the Shareholders Agreement, but this seat currently remains unfilled.

In addition to the two (2) Shareholder Directors appointed in accordance with the Shareholders Agreement, the Board has nominated eleven (11) individuals to serve as Class B directors based upon the recommendation of the Nominating and Corporate Governance Committee. Ten of these individuals are incumbent directors and were elected by the shareholders at our 2025 annual general meeting. The other remaining individual, Peter W. Wilson, is being nominated for the first time as a potential director based upon the recommendation of the Nominating and Corporate Governance Committee following a comprehensive search and review of suitable candidates. This process incorporated the valuable referrals of industry contacts of our executive officers, which played a crucial role in identifying this qualified candidate.

Our bye-laws provide that our Board may appoint such officers as it may determine. This provides the Board with the flexibility to combine or separate the positions of Chairperson of the Board and Chief Executive Officer should it determine that utilizing one or the other structure would be in the best interests of the Company. David A. Brown, a non-executive director, continues to serve as Chairperson of the Board.

Our Board has concluded that our current leadership structure is appropriate at this time in light of the Board’s size and the cooperative and dynamic working relationship among our directors, including the Shareholder Directors and independent directors. However, our Board will continue to periodically review our leadership structure and may make such changes in the future as it deems appropriate.


Hamilton Insurance Group, Ltd.			2026 Proxy Statement						12

Shareholder Directors

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


Bradley Cooper			Mr. Cooper, age 59, has served as a director of the Company since 2024. Mr. Cooper is a Managing Partner of Capital Z Partners, a private equity fund focused on investing in the financial services sector. Prior to founding Capital Z in 1990, Mr. Cooper was an investment banker in the Financial Institutions Group of Salomon Brothers (now Citigroup). He has extensive Board experience with both publicly traded and privately held companies, having served on, and chaired many committees. Mr. Cooper served on the Board of non-profit Make-A-Wish Foundation of Metro New York for 16 years, the final three as Chair, and the University of Michigan, Stephen M. Ross School of Business Advisory Board for approximately 8 years. We believe that Mr. Cooper’s extensive experience in the financial services sector and business leadership experience qualify him to serve on the Company’s Board. Mr. Cooper was appointed as a director of the Company pursuant to Hopkins Holdings, LLC’s right under t

SEC Form DEF 14A filed by Hamilton Insurance Group Ltd.