2024 Proxy PDF

SAFETY INSURANCE GROUP, INC.

20 Custom House Street, Boston, Massachusetts 02110

April 1, 2025

To Our Stockholders:

I am pleased to invite you to attend the 2025 Annual Meeting of Stockholders of Safety Insurance Group, Inc. (the "2025 Annual Meeting"), which will be held at 10:00 AM on May 14, 2025, at our headquarters, 20 Custom House Street, Boston, Massachusetts 02110. While attendance in person will be permitted, stockholders will be able to listen to a live teleconference of the meeting by dialing in at (917) 722-6956. The participation code for the meeting is 782770293. We will be taking questions from stockholders only in advance of the meeting to reduce the risk of technology problems. If you have questions, please email them to[email protected]by May 9, 2025.

Included with this letter are the Notice of Annual Meeting of Stockholders, a proxy statement detailing the business to be conducted at the Annual Meeting and a proxy card.

If you plan to attend the meeting, please bring a form of personal identification with you and, if you are acting as proxy for another shareholder, please bring written confirmation from the shareholder for whom you are acting as proxy.

Please be advised that stockholders will not be deemed to be "present" and will not be able to vote their shares, or revoke or change a previously submitted vote, at the Annual Meeting by participating in the live audio presentation of the Annual Meeting. As a result, to ensure that your vote is counted at the Annual Meeting, the Company strongly urges shareholders to submit their proxies or votes in advance of the Annual Meeting using one of the available methods described in the Proxy Statement and proxy card.

Whether or not you expect to attend the meeting, please sign and retuthe enclosed proxy card in the envelope provided. Your cooperation will assure that your shares are voted and will also greatly assist our officers in preparing for the meeting. If you attend the meeting, you may withdraw any proxy previously given and vote your shares in person if you so desire.

The matters to be voted on at the 2025 Annual Meeting are:

• (i) the election of two directors;

• (ii) the ratification, on an advisory (non-binding) basis, of the appointment of Deloitte & Touche LLP as our independent registered public accounting firm for 2025; and (iii) the approval, on an advisory (non-binding) basis, of our named executive officer compensation.

Sincerely,

George M. Murphy

Presidentand Chief Executive Officer, Chairperson of the Board of Directors

20 Custom House Street, Boston, Massachusetts 02110

NOTICE OF ANNUAL MEETING OF STOCKHOLDERS

TO BE HELD MAY 14, 2025

April 1, 2025

To Our Stockholders:

The 2025 Annual Meeting of Stockholders of Safety Insurance Group, Inc. (the "Company") will be held on, May 14, 2025 at 10:00 AM local time, at our headquarters, 20 Custom House Street, Boston, Massachusetts 02110. At this meeting, you will be asked to consider and vote upon the following:

• 1. a proposal to elect two of the Company's directors to Class II with a term ending 2028;

• 2. to ratify the appointment of Deloitte & Touche LLP as the Company's independent registered public accounting firm for 2025;

• 3. to provide an advisory vote on the compensation of the named executive officers as disclosed in this Proxy Statement; and

• 4. to transact such other business as may properly come before the Annual Meeting or any adjournment or any postponement thereof.

These items of business are more fully described in the proxy statement accompanying this Notice.

Our Board has fixed the close of business on March 17, 2025, as the record date for the determination of stockholders entitled to notice of and to vote at the Annual Meeting of Stockholders of the Company (the "2025 Annual Meeting").

OUR BOARD UNANIMOUSLY RECOMMENDS VOTING "FOR" THE ELECTION OF OUR BOARD'S NOMINEES UNDER PROPOSAL 1, and "FOR" PROPOSALS 2 and 3, USING THE ENCLOSED PROXY CARD.

By Order of the Board of Directors,

CHRISTOPHER T. WHITFORD

Vice President, Chief Financial Officer and Secretary

Important Notice Regarding the Availability of Proxy Materials for

Our 2025 Annual Meeting of Stockholders to Be Held on May 14, 2025

The accompanying Proxy Statement and our 2024 Annual Report to Our Stockholders are available for viewing, printing and downloading atwww.proxyvote.comandhttp://materials.proxyvote.com/78648T.

Table of Contents

Page

GENERAL INFORMATION 1

PROPOSAL 1ELECTION OF THE COMPANY'S DIRECTORS 3

PROPOSAL 2RATIFICATION OF APPOINTMENT OF DELOITTE & TOUCHE LLP

AS THE COMPANY'S INDEPENDENT REGISTERED PUBLIC ACCOUNTING

FIRM FOR 202513

PROPOSAL 3ADVISORY VOTE ON EXECUTIVE COMPENSATION 15

EXECUTIVE OFFICERS 16

EXECUTIVE COMPENSATION 18

Compensation Discussion and Analysis 18

Compensation Committee Report 31

Compensation Policies and Practices as They Relate to the Company's Risk Management 32

Summary Compensation Table 33

Grants of Plan-Based Awards 34

Outstanding Equity Awards at Fiscal Year-End 37

Restricted Stock Vested 38

Pension Benefits Table 38

Nonqualified Deferred Compensation 39

Potential Payments Upon Termination or Change in Control 40

DIRECTOR COMPENSATION 44

REPORT OF THE AUDIT COMMITTEE 45

SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS, DIRECTORS AND

MANAGEMENT46

COMPENSATION COMMITTEE INTERLOCKS AND INSIDER PARTICIPATION 47

PAY RATIO 48

CERTAIN RELATIONSHIPS AND RELATED TRANSACTIONS 52

OTHER MATTERS 53

SAFETY INSURANCE GROUP, INC.

20 Custom House Street, Boston, Massachusetts 02110

PROXY STATEMENT

FOR ANNUAL MEETING OF STOCKHOLDERS

TO BE HELD MAY 14, 2025

GENERAL INFORMATION

This Proxy Statement is being furnished in connection with the solicitation of proxies on behalf of the Board of Directors (the "Board") of Safety Insurance Group, Inc. (the "Company" or "Safety" or "we") for the 2025 Annual Meeting of Stockholders to be held on May 14, 2025 at the Company's headquarters located at 20 Custom House Street, Boston, Massachusetts 02110 (the "2025 Annual Meeting").

The record date for determining stockholders entitled to vote at the 2025 Annual Meeting has been fixed at the close of business on March 17, 2025 (the "Record Date"). As of the Record Date, 14,893,703 shares of the Company's common stock, par value $0.01 per share (the "Common Stock"), were outstanding and entitled to be voted. Every stockholder will be entitled to one vote for each share of Common Stock recorded in his or her name on the Company's books as of the Record Date. The Company mailed this Proxy Statement and the related form of proxy (the "Proxy") on or about April 1, 2025.

If you timely retua validly executed proxy card without indicating how your shares should be voted on a matter and you do not revoke your proxy, your proxy will be voted in accordance with the Board's recommendation as follows:

Board

With respect to Proposal 1, Election of the Company's Directors, the shares of Common Stock represented by the enclosed Proxy will be voted as directed by the shareholder. Abstentions are not counted as a vote cast either "for" or "against" the nominee's election. The Board adopted Amended and Restated Bylaws of the Company effective as of March 30, 2020 under which a director shall be elected by a majority of the votes cast in an uncontested election at which a quorum (a majority of issued and outstanding shares of Common Stock entitled to vote) is present. For the 2025 Annual Meeting, so long as a quorum is present either in person or by proxy, a majority of the votes properly cast is required to elect each director. Votes withheld from a director nominee, abstentions and broker non-votes (when a registered broker holding a customer's shares in the name of the broker has not received voting instructions on a matter from the customer and is barred from exercising discretionary authority to vote on the matter, which the broker indicates on the proxy card) will betreated as present at the 2025 Annual Meeting for the purpose of determining a quorum but will not be counted as votes cast.

With respect to Proposal 2, Ratification of Appointment of Independent Registered Public Accounting Firm, an affirmative vote of a majority of the shares present or represented and entitled to vote on such proposal is required for approval. Abstentions are included in the number of shares present or represented and entitled to vote on the proposal and therefore have the practical effect of a vote against the proposal.

With respect to Proposal 3, Advisory Vote on Executive Compensation, an affirmative vote of a majority of the shares present or represented and entitled to vote on such proposal is required for approval (on a non-binding, advisory basis). Abstentions are included in the number of shares present or represented and entitled to vote on the proposal and therefore have the practical effect of a vote against the proposal. Your vote is advisory and will not be binding upon the Company, the Board of Directors, or the Compensation Committee. However, the Board of Directors and the Compensation Committee will take into account the outcome of the vote when considering future executive compensation arrangements.

Any stockholder giving a Proxy may revoke it at any time before it is exercised by delivering written notice thereof to the Secretary. Any stockholder attending the 2025 Annual Meeting may vote in person whether or not the stockholder has previously filed a Proxy. Presence at the 2025 Annual Meeting by a stockholder who has signed a Proxy, however, does not in itself revoke the Proxy. The enclosed Proxy is being solicited by the Board.

The Company's Annual Report to Stockholders for the fiscal year ended December 31, 2024, including financial statements and the report of the Company's independent registered public accounting firm, Deloitte & Touche LLP, thereon, accompanies this Proxy Statement. The Annual Report to Stockholders is neither a part of this Proxy Statement nor incorporated herein by reference.

The voting results of the 2025 Annual Meeting will be published no later than four business days after the Annual Meeting on a Form 8-K filed with the Securities and Exchange Commission.

PROPOSAL 1

ELECTION OF THE COMPANY'S DIRECTORS

The Board consists of seven members and three classes. Each class serves three years, with terms of office of the respective classes expiring in successive years.

Two Directors, whose terms expire at this year's 2025 Annual Meeting, Deborah E. Gray and George M. Murphy, have been nominated for election to a three-year term ending at the 2028 Annual Meeting of Stockholders and until a successor, if any, is elected and duly qualified. The remaining five directors will continue to serve in accordance with their terms.

THE BOARD RECOMMENDS VOTINGFORPROPOSAL 1 WHICH CALLS FOR THE ELECTION OF THE 2025 NOMINEES.

* Nominated at the 2025 Annual Meeting to a term ending in 2028. ** As of March 17, 2025.

• (1) Member of the Audit Committee.

• (2) Member of the Compensation Committee.

• (3) Member of the Nominating and Governance Committee.

• (4) Member of the Investment Committee.

• (C) Chairperson of the Committee referenced.

Each of our directors brings to our board extensive management and leadership experience gained through their service as executives and, in several cases, chief executive officers of diverse businesses. In these executive roles, they have taken hands-on, day-to-day responsibility for strategy and operations, including management of capital, risk and business cycles. The nominating committee's process to recommend qualified director candidates is described under Nominating and Governance Committee Policies.

BrophyFarinaGrayLangwellMeehanMoranMurphy

Business Management Diversity

X

X

XX

X

Financial Statement / Audit Independence

Insurance Industry Investment

X X X

X X X

X

X X X X

XX X X X

X

X

Legal or Regulatory

Public Company Experience Risk Management / ESG Technology and Information Security

X X

X X X

X X X

X X

X

XX X X X X

X

The following information with respect to the principal occupation, business experience, recent business activities involving the Company and other affiliations of the nominees and directors has been furnished to the Company by the nominees and directors.

Nominees for Director

Deborah E. Graywas appointed Director of the Company on March 24, 2022 and currently serves on the Compensation and Nominating and Governance Committees. Ms. Gray has served in various General Counsel roles over her 30-year career, including most recently providing her expertise as outside GeneralCounsel to several companies. She is also currently the Vice President and General Counsel of The Achievement Network (since 2014), a private, non-profit national education and technology organization where she leads all day-to-day legal, data privacy and security, and compliance initiatives. Prior to this role, Ms. Gray served as Vice President, General Counsel and Secretary at Acquia, Inc., a Software-as-a-Service (SaaS) company, from October 2011 to December 2013, where she led the creation and build out of its global legal, data security and corporate compliance functions including M&A, commercial contracts, licensing, real estate, employment, corporate and Board governance. From 2002 to 2011, Ms. Gray was with Charles River Laboratories International, Inc., a U.S. life sciences company providing pre-clinical/clinical lab services for pharma, medical devices and biotech companies. At Charles River Laboratories, she was responsible for corporate, licensing, employment law, SEC and NYSE reporting and compliance, corporate governance, M&A, and general commercial contracts. In 2006, she took on the role of chief employment counsel for offices in 19 states and various locations in Canada, Japan, China, India and Europe. Previous to this, Ms. Gray was a member of the Executive Team at Sapient Corporation, a publicly traded professional services tech company, as Vice President, General Counsel, and Assistant Secretary, and with Harcourt General, a publicly traded holding company, as Senior Corporate & SEC Counsel. Ms. Gray began her legal career at WilmerHale in Boston where she was a Junior Partner specializing in mergers and acquisitions, initial public offerings, and SEC compliance matters.

Ms. Gray has served on several non-profit boards including, The Home for Little Wanderers, the largest child welfare organization in the country, where she co-chaired the Nominating & Governance Committee and chaired the Risk Management Committee for many years. Previously, she was a Trustee of Colby College and an Overseer of the Boston Symphony Orchestra. Ms. Gray graduated with a B.A. from Colby College and a J.D. from Boston College Law School. Her legal and business expertise with high-growth companies, ranging from start-ups to publicly traded multibillion-dollar corporations, are beneficial to Safety, particularly in relation to risk management, compliance, data privacy and security, and corporate governance matters. We believe that Ms. Gray's corporate governance and legal expertise enable her to provide valuable insight and advice regarding decisions and other matters of importance to the Company, which we believe well qualify her to serve as a Director.

George M. Murphy, CPCU, was appointed President and Chief Executive Officer of the Company effective April 1, 2016. He previously was the Vice President of Marketing since October 1, 2005. Mr. Murphy was appointed to the Board of Directors and to the Investment Committee in February 2016. Mr. Murphy has been employed by the Insurance Subsidiaries (defined below) of the Company for over 32 years. On March 3, 2023, Mr. Murphy was appointed as Chairperson of the Board. Mr. Murphy is also on the Board of Trustees of the Insurance Library Association of Boston. Mr. Murphy's leadership roles in the Company and our insurance subsidiaries which includes developing a deep understanding of our business as well strong personal relationships with Safety's network of independent agents along with his knowledge of finance, regulation, corporate governance and other matters affecting public companies, make him well-qualified to serve on our Board of Directors.

Directors Continuing in Office

John D. Farinawas appointed Director of the Company on March 24, 2022. Mr. Farina was appointed Chairperson of the Audit Committee in May 2023 and also serves as a member of the Nominating and Governance Committee. Mr. Farina is a retired partner of PricewaterhouseCoopers ("PwC"), where he spent 35 years advising both domestic and multinational Fortune 500 companies on financial accounting, regulatory, and

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Disclaimer

Safety Insurance Group Inc. published this content on April 02, 2025, and is solely responsible for the information contained herein. Distributed via Public Technologies (PUBT), unedited and unaltered, on April 02, 2025 at 16:44 UTC.