Hamilton Insurance Group, Ltd.

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

Filed by the Registrant ☒

Filed by a Party other than the Registrant ☐

Check the appropriate box:

HAMILTON INSURANCE GROUP, LTD.

(Name of Registrant as Specified In Its Charter)

(Name of Person(s) Filing Proxy Statement, if other than the Registrant)

Payment of Filing Fee (Check the appropriate box):

March 27, 2025

Dear Shareholder,

We are pleased to invite you to attend the 2025 Annual General Meeting of Shareholders of Hamilton Insurance Group, Ltd. ("Hamilton"). The attached proxy statement contains important information regarding the agenda for the meeting and voting instructions.

2024 was a transformative year for Hamilton, characterized by significant achievements. As we navigated our inaugural full calendar year as a public company, we successfully expanded our most attractive business lines and adeptly deployed capital across both the insurance and reinsurance sectors. We maintained a sharp focus on execution, capitalized on promising market opportunities and made remarkable progress in achieving our strategic and operational goals.

Our achievements are a testament to the hard work and dedication of our employees, an extremely talented team of professionals that know how and when to push the organization forward, all while maintaining our rigorous underwriting and risk management discipline standards. Thanks to their efforts, we have grown our business, fortified our foundation and positioned Hamilton to thrive and serve our customers for years to come.

We take immense pride in what Hamilton has accomplished, and we are even more excited about the future.

I encourage you to read the attached proxy statement, which will serve as your guide to the business to be conducted at the meeting. The meeting will be held virtuallyon May 15, 2025 at 9am Eastern Time and can be accessed via the following link: www.virtualshareholdermeeting.com/HG2025.

Thank you for your continued support.

Sincerely,

David A. Brown, Chairman

Notice of 2025 Annual General

Meeting of Shareholders

On behalf of the Hamilton Insurance Group, Ltd. ("Hamilton" or the "Company") Board of Directors, you are cordially invited to attend the Hamilton 2025 Annual General Meeting of Shareholders (the “Annual Meeting" or “Annual General Meeting”).

Meeting Details

How to Vote

Matters to Be Voted On

Proxies

The Hamilton Board of Directors (the "Board of Directors" or "Board") is soliciting proxies to be voted at the Annual Meeting on May 15, 2025, and at any postponed or reconvened meeting. Shareholders of record are being mailed, sent or given, on or about March 27, 2025, a Notice of Internet Availability of Proxy Materials providing instructions on how to access the Proxy Materials on the Internet.

Accessing the 2025 Annual General Meeting

Your vote is important—we want to hear from you and all of our Shareholders.

We encourage you to read the accompanying proxy statement, which contains important information, including a description of the business that will be acted upon at the Annual General Meeting.

To participate in the Annual General Meeting, you will need the 16-digit control number included on your Notice of Internet Availability of Proxy Materials, on your proxy card, or any other voting instruction form accompanying these materials.

We have adopted a virtual meeting format for the Annual General Meeting, which grants our Shareholders the ability to attend, vote and submit questions via the internet. As this format allows for Shareholder participation from any location, we believe this structure fosters a more meaningful interaction between management and our Shareholders.

Please refer to "Voting and Meeting Information" in the attached proxy statement for additional information on how to vote your shares and attend the meeting virtually.

By order of the Board of Directors,

Gemma Carreiro

General Counsel & Secretary

March 27, 2025

Important Notice Regarding the Availability of Proxy Materials to be held virtually via the Internet on May 15, 2025. Our 2025 proxy statement as well as our 2024 Annual Report are available free of charge in the investors section of our website at www.hamiltongroup.com.

Table of Contents

Cautionary Note Regarding Forward-Looking Statements

Certain matters we discuss in this proxy statement may constitute forward-looking statements pursuant to the safe harbor provisions 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 in a number of places throughout this proxy statement and relate to matters such as our industry, growth strategy, goals and expectations concerning our market position, future operations, margins, profitability, capital expenditures, liquidity and capital resources and other financial and operating information, corporate governance practices and strategies; 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, or changes in circumstances that are difficult to predict or quantify. Our expectations, beliefs, and projections are expressed in good faith and we believe there is a reasonable basis for them. However, there can be no assurance that management’s expectations, beliefs and projections will be achieved and actual results may vary materially from what is expressed in or indicated by the forward-looking statements.

Factors that can cause results to differ materially include those described under “Special Note Regarding Forward-Looking Statements” in Hamilton's most recent Form 10-K filed with the SEC and available on our website. There may be other factors that could cause our actual results to differ materially from the forward-looking statements. You should evaluate all forward-looking statements made in this proxy statement in the context of these risks and uncertainties.

We caution you that the risks, uncertainties, and other factors referenced above may not contain all of the risks, uncertainties and other factors that are important to you. In addition, we cannot assure you that we will realize the results, benefits, or developments that we expect or anticipate or, even if substantially realized, that they will result in the consequences or affect us or our business in the way expected. All forward-looking statements in this proxy statement apply only as of the date of this proxy statement and are expressly qualified in their entirety by the cautionary statements. 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" and "Hamilton" refer to Hamilton Insurance Group, Ltd. and its consolidated subsidiaries.