2025 Proxy Statement

Important Notice Regarding the Availability of Proxy Materials for the Shareholder Meeting to be Held on May 14, 2025 at Fairmont Hamilton Princess, 76 Pitts Bay Road, Hamilton, Bermuda at 10:00 a.m. local time.

The proxy statement and annual report to shareholders are available at

https://investors.everestglobal.com/financials/annual-reports-and-proxy-statements/default.aspx

PROXY STATEMENT

ANNUAL GENERAL MEETING OF SHAREHOLDERS

May 14, 2025

GENERAL INFORMATION

The enclosed Proxy Card is being solicited on behalf of the Board of Directors (the "Board") of Everest Group, Ltd., a Bermuda company (the "Company", "Everest Group" or, unless the context otherwise requires, "Everest") for use at the 2025 Annual General Meeting of Shareholders (the "AGM"), to be held on May 14, 2025, and at any adjournment thereof. It may be revoked at any time before it is exercised by giving a later-dated proxy, notifying the Corporate Secretary of the Company in writing at the Company's registered office at Clarendon House, 2 Church Street, Hamilton HM 11, Bermuda, or voting in person at the Annual General Meeting. All shares represented at the meeting by properly executed proxies will be voted as specified and, unless otherwise specified, will be voted: (1) for the election of John J. Amore, William F. Galtney Jr., John A. Graf, Meryl Hartzband, John Howard, Gerri Losquadro, Hazel McNeilage, Roger M. Singer and Jim Williamson as directors of the Company; (2) for the appointment of KPMG LLP ("KPMG"), an independent registered public accounting firm, as the Company's independent auditor for the fiscal year ending December 31, 2025 and for authorizing the Board acting through its Audit Committee to determine the independent auditor's remuneration; (3) for the approval, by non-binding advisory vote, of the 2024 compensation paid to the Named Executive Officers (as defined herein); (4) for the approval of the Everest Group, Ltd. 2025 Employee Stock Purchase Plan and (5) for the approval of amendments to the Company's bye-laws (as further described in this Proxy Statement).

Only shareholders of record at the close of business on March 17, 2025 will be entitled to vote at the meeting. On that date, 52,378,142 Common Shares, par value $.01 per share ("Common Shares"), were outstanding. However, this amount includes 9,719,971 Common Shares held by Everest Re Advisors, Ltd. ("Re Advisors"), the Company's subsidiary. As provided in the Company's Bye-laws, Re Advisors may vote only 9.9% of its shares. The outstanding share amount also excludes 58,727 shares with no voting rights. The limitation of Re Advisors voting shares to 5,185,436 and the exclusion of 58,727 shares with no voting rights results in 47,784,880 Common Shares entitled to vote.

The election of each nominee for director and the approval of all other matters to be voted upon at the Annual General Meeting require the affirmative vote of a majority of the votes cast at the Annual General Meeting, provided there is a quorum consisting of no fewer than two persons present in person or by proxy holding in the aggregate more than 50% of the issued and outstanding Common Shares entitled to attend and vote at the Annual General Meeting. The Company has appointed inspectors of election to count votes cast in person or by proxy. Common Shares owned by shareholders who are present in person or by proxy at the Annual General Meeting but who elect to abstain from voting will be counted towards the presence of a quorum. However, such Common Shares and Common Shares owned by shareholders and not voted in person or by proxy at the Annual General Meeting (including "broker non- votes") will not be included in any tally of votes cast and will therefore have no effect on the outcomes of votes to elect a director or approve any other matter before the shareholders.

All references in this document to "$" or "dollars" are references to the currency of the United States of America.

The Company knows of no specific matter to be brought before the Annual General Meeting that is not referred to in the attached Notice of Annual General Meeting of Shareholders and this Proxy Statement. If any such matter comes before the meeting, including any shareholder proposal properly made, the proxy holders will vote proxies in accordance with their best judgment with respect to such matters. To be properly made, a shareholder proposal must comply with the Company's Bye-laws and, in order for any matter to come before the meeting, it must relate to matters referred to in the attached Notice of Annual General Meeting.

2025 Proxy Statement 1

Proxy Statement Summary

PROXY STATEMENT

SUMMARY

This summary highlights certain information contained in the Company's Proxy Statement. The summary does not contain all of the information that you should consider, and we encourage you to read the entire Proxy Statement carefully.

Voting Matters and Board's Voting Recommendations

ProposalBoard's Voting Recommendation Page

Director Nominees

1. Compensation CommitteeNGC Nominating and Governance Committee

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Proxy Statement Summary

Corporate Governance Highlights

Board Independence Standards

The Board has adopted director independence standards as set forth by the New York Stock Exchange ("NYSE").

Director Independence on Key Committees

The Board's Audit, Compensation and Nominating and Governance Committees are composed entirely of independent directors.

No Over-Boarding

No member of the Board of Directors sits on the board of directors of more than two other publicly traded companies.

*Board to be reduced to 9 members (3 women, 6 men) upon conclusion of the AGM

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Compensation Best Practices:

Award Performance Share Units as an

• element of long-term incentive compensation
• Engage with shareholders on executive compensation practices
  Maintain stock ownership guidelines for
• Executive Officers(1) and Non-Management Directors(2)

1. Six times base salary for CEO; three times base salary for other Named Executive Officers (as defined herein).
2. Five times annual retainer.
3. CEO participates in the Senior Executive Change in Control Plan ("CIC Plan"), along with the other Named Executive Officers.

4 2025 Proxy Statement

Proxy Statement Summary

2024 Financial results reflected Everest's resilience amidst challenging business conditions. Despite another year exceeding $100 billion in global insured losses from natural catastrophes, the Company's Reinsurance business achieved total written premium of approximately $13 billion and an 89.7% total combined ratio. In the global Insurance business, total gross written premium was over $5 billion in 2024, with excellent returns from many business lines, particularly North America and international Property and Specialty. The Company also advanced the international insurance strategy, and achieved several important milestones in Insurance, including $1.5 billion of gross written premium. In 2024, Everest took decisive action to address the impact of social inflation and legal system abuse on the North American Casualty insurance business, including aggressive underwriting and strengthening its reserves to position the Company for sustainable profitability.

On a consolidated basis, the Company earned $1.4 billion of net income in the fiscal year ended December 31, 2024 ("fiscal year 2024"). Gross written premiums grew by 9.1% to $18.2 billion, and the Company generated $1.3 billion of net operating income and a 9.0% after-tax operating retuon equity.(2) In fiscal year 2024, the Company generated a Total Shareholder Retu("TSR") of 9.2% and net investment income increased over $500 million to approximately $2.0 billion.

In 2024, we increased our quarterly dividend and returned $334 million to shareholders in the form of dividends.

1. Please see Appendix A for explanations and available reconciliations of the non-generally accepted accounting principles ("GAAP") measures used described Company performance in this Proxy Statement.
2. Gross Written Premium growth is presented on a comparable basis, reflecting constant currency basis and excluding reinstatement premiums
3. Excludes approximately $68 million of profit commission related to loss reserve releases. When including this profit commission, Everest's reported attritional combined ratio was 88.1% for the year ended December 31, 2024.
4. Gross Written Premium growth, Attritional Combined Ratio, Net Operating Income, TSR and Net Operating Income ROE are non-GAAP measures. Please see Appendix A for further information and available reconciliations.
5. TSR unless otherwise noted herein, means annual growth in book value per common share outstanding (excluding Net Unrealized Depreciation/ appreciation of Fixed Maturity, available for sale investments) plus dividends per share.

2025 Proxy Statement 5

Proxy Statement Summary

Ratings

TSR, a non-GAAP measure, is defined as annual growth in book value per common share outstanding (excluding Net Unrealized Depreciation/appreciation of Fixed Maturity, available for sale investments) plus dividends per share. Operating Income, also referred to as after-tax net operating income (loss) is also a non-GAAP measure. Please see Exhibit A for further information.

6 2025 Proxy Statement

Proposal No. 1- Election of Directors

PROPOSAL NO. 1 - ELECTION OF DIRECTORS

The Board recommends that you vote FOR the director nominees described below. Proxies will be so voted except to the extent that shareholders specify otherwise in their proxies.

At the 2025 Annual General Meeting ("AGM"), the nominees for director positions are to be elected to serve until the 2026 Annual General Meeting of Shareholders or until their qualified successors are elected or until such director's office is otherwise vacated. At its regularly scheduled meeting in February 2025, the Nominating and Governance Committee recommended to the Board the nominations of John J. Amore, William F. Galtney Jr., John A. Graf, Meryl Hartzband, Gerri Losquadro, Hazel McNeilage, Roger M. Singer, Joseph V. Taranto and Jim Williamson, all of whom are currently directors of the Company. The Board accepted the Nominating and Governance Committee's recommendations, and each nominee accepted his or her nomination. By resolution adopted by unanimous written consent on March 24, 2025, the Board amended the slate (i) to exclude Mr. Taranto, in light of his preference to retire from the Board, thereby determining that Mr. Taranto's service on the Board would terminate upon the conclusion of the AGM on May 14,

2025 ,and (ii) to include John Howard, who was elected to the Board effective March 6, 2025. Additionally, the Board voted to reduce the size of the Board to nine members following the AGM. It is not expected that any of the nominees will become unavailable for election as a director, but if any nominee should become unavailable prior to the meeting, proxies will be voted for such persons as the Board shall recommend, unless the Board reduces the number of directors accordingly. There are no arrangements or understandings between any director or any nominee for election as a director and any other person pursuant to which such person was selected as a director or nominee.

Important Factors in Assessing Board Composition

The Nominating and Governance Committee strives to maintain an engaged, independent Board with broad and diverse experience, skills and judgment that is committed to representing the long-term interests of our shareholders. In evaluating director candidates and considering incumbent directors for nomination to the Board, the Nominating and Governance Committee considers each nominee's character, independence, leadership, financial literacy, personal and professional accomplishments, industry knowledge and experience.

For incumbent directors, the factors also include attendance and past performance on the Board and its committees. Each director nominee has a demonstrated record of accomplishment in areas relevant to the Company's business and qualifications that contribute to the Board's ability to effectively function in its oversight role.

The Nominating and Governance Committee seeks current and potential directors who will collectively bring to the Board a variety of skills, including:

• Leadership: Demonstrated ability to hold significant leadership positions and effectively manage complex organizations is important to evaluating and developing key management talent.
• Insurance and/or Reinsurance Industry Experience: Experience in the insurance and/or reinsurance markets is critical to strategic planning and oversight of our business operations.
• Risk Management: Experience in identifying, assessing and managing risks is critical to oversight of current and emerging organizational and systemic risks in order to inform and adapt the Company's strategic planning.
• Regulatory: An understanding of both the laws and regulations that impact our heavily regulated industry and the impact of government actions and public policy are important to oversight of insurance operations.
• Finance and Accounting: Financial experience and literacy are essential for understanding and overseeing our financial reporting, investment performance and internal controls to ensure transparency and accuracy.
• Corporate Governance: Understanding of corporate governance matters is essential to ensuring effective governance of the Company and protecting shareholder interests.
• Business Operations: A practical understanding of developing, implementing and assessing our business operations and processes and experience making strategic decisions, including the assessment of our operating plan, risk management and long-term sustainability strategy, are critical to the oversight of our business.
• Information Technology/Cybersecurity: In addition, comprehensive oversight requires an understanding of information systems, data and technology used in our business operations and processes, the role of data and technology systems in relation to our corporate strategy as well as a recognition of the risk management aspects of cyber risks and cybersecurity.
• International: Experience in and knowledge of global insurance and financial markets are especially important in understanding and reviewing our business and strategy.

2025 Proxy Statement 7