DEF 14A of SiriusPoint Ltd, Apr 9, 2024

DEF 14A of SiriusPoint Ltd

Filed Apr 9, 2024 · FY20230001999371-24-004620

Open on EDGAR

  1. Safe Harbor Statement Regarding Forward-Looking Statements

    | 46 | Director Compensation | | 49 | EXECUTIVE OFFICERS | | 52 | EXECUTIVE COMPENSATION | | 52 | PROPOSAL 2―ADVISORY VOTE TO APPROVE EXECUTIVE COMPENSATION (SAY-ON-PAY) | | 53 | Compensation Discussion and Analysis | | 75 | Compensation Committee Report | | 76 | Compensation Tables | | 91 | CEO Pay Ratio Disclosure | | 92 | Pay Versus Performance | | 98 | PROPOSAL 3―APPOINTMENT OF INDEPENDENT AUDITOR & DETERMINE THE INDEPENDENT AUDITOR’S | | 99 | Independent Registered Public Accounting Firm Fees | | 99 | Policy on Audit Committee Pre-Approval of Audit and Permissible Non-Audit Services | | 100 | Report of the Audit Committee | | 102 | STOCK OWNERSHIP INFORMATION | | 102 | Security Ownership of Certain Beneficial Owners and Management | | 106 | Delinquent Section 16(a) Reports | | 107 | General Information | | 107 | Questions and Answers | | 118 | ADDITIONAL INFORMATION | | 118 | Submitting Proxy Proposals and Director Nominations for the Next Annual General Meeting | | 121 | Other Matters | | 122 | Appendix A: Non-GAAP Measures |

  2. INFORMATION REGARDING THE CLASS II DIRECTOR NOMINEES FOR ELECTION TO THE BOARD

    INFORMATION REGARDING THE CLASS II DIRECTOR NOMINEES FOR ELECTION TO THE BOARD Set forth below is biographical information concerning the nominees standing for election at the Annual General Meeting. Included in the biographical information for the nominee is a description of each nominee’s specific experience, qualifications, attributes and skills that the Governance and Nominating Committee and the Board considered in determining whether to recommend the nominee for election to the Board. Our director nominees hold and have held senior positions as leaders of various large, complex businesses and organizations, demonstrating their ability to develop and execute significant policy and operational objectives at the highest levels. Our nominees include current and former chief executive officers, chief financial officers, founders and members of senior management of large, global businesses. Our Board considered all of the aforementioned attributes when deciding to re-nominate the following directors.

  3. INFORMATION REGARDING THE CLASS II DIRECTOR NOMINEES FOR ELECTION TO THE BOARD

    | MEHDI A. MAHMUD | KEY EXPERIENCE AND QUALIFICATIONS The Board considered Mr. Mahmud’s extensive leadership, digital strategy and investment experience and his qualification as an independent director, and concluded that Mr. Mahmud should continue to serve as a director because he brings significant experience in managing investment portfolios to the Board. CAREER HIGHLIGHTS • First Eagle Investment Management, an investment management company and adviser to First Eagle Funds ◦ President and Chief Executive Officer (March 2016 to present) • First Eagle Funds, an investment fund ◦ President (March 2016 to present) • Jennison Associates ◦ CEO and Chairman of the Board (2003 to 2016) | • Jennison Associates (continued) ◦ Held several senior management positions relating to: ▪ product and business strategy ▪ investment supervision of the firm’s value, small-cap, opportunistic and income-equity capabilities ▪ oversight of key support areas, including institutional, retail and sub-advisory client activities • J.P. Morgan Investment Management and Credit Suisse Asset Management ◦ Served in a variety of investment and management roles EDUCATION • BS in Electrical Engineering, Yale University | | | | | | CLASS II Age 51 Independent Director since August 2020 Committees • Compensation • Governance and Nominating • Investment | | |

  4. INFORMATION REGARDING THE CLASS II DIRECTOR NOMINEES FOR ELECTION TO THE BOARD

    | JASON ROBART | KEY EXPERIENCE AND QUALIFICATIONS The Board considered Mr. Robart’s extensive experience as an accomplished executive and substantial experience in a range of areas including business strategy, healthcare, venture investing, digital strategy and human capital management. The Board concluded that he should serve on the Board because he brings extensive leadership experience in developing early stage growth and health insurance companies to the Board and his deep experience in human capital management. CAREER HIGHLIGHTS • Seae Ventures, a healthcare service and technology venture fund ◦ Co-Founder and Managing Director (2019 to present) • Blue Cross Blue Shield Massachusetts, an insurance company ◦ Chief Strategy Officer (2011 to 2018) • Zaffre Investments, a wholly-owned subsidiary of Blue Cross Blue Shield Massachusetts ◦ President and Chief Executive Officer (2014 to 2018) | • Mercer Human Resources Consulting ◦ Principal (2003 to 2009) • Ceridian Performance Partners, Canada ◦ President OTHER DIRECTORSHIPS AND ENGAGEMENTS • Blue Cross Blue Shield, Vermont • Several Seae Ventures companies, including Hurdle, Kiyatec, MyMeds and Moving Analytics EDUCATION • BA in Political Science, Middlebury College | | | | | | CLASS II Age 58 Independent Director since March 2022 Committees • Audit • Compensation • Investment | | |

  5. INFORMATION REGARDING THE CLASS II DIRECTOR NOMINEES FOR ELECTION TO THE BOARD

    | DANIEL S. LOEB | KEY EXPERIENCE AND QUALIFICATIONS The Board considered Mr. Loeb’s extensive qualifications and experience as the Chief Executive Officer and Chief Investment Officer of Third Point LLC, and concluded that he should continue to serve on the Board because he brings experience in investment management, legal and regulatory matters, corporate governance, risk management and business development to the Board. CAREER HIGHLIGHTS • Third Point LLC, an investment adviser based in New York ◦ Chief Executive Officer and Chief Investment Officer (1995 to present) | PRIOR PUBLIC COMPANY BOARDS • Sotheby’s, Director EDUCATION • A.B., Columbia University | | | | | | CLASS II Age 62 Director since May 2022 | | |

  6. INFORMATION REGARDING THE CLASS II DIRECTOR NOMINEES FOR ELECTION TO THE BOARD

    | BRONEK MASOJADA | KEY EXPERIENCE AND QUALIFICATIONS The Board considered Mr. Masojada’s extensive experience and qualifications as Chair of Placing Platform Ltd. and who is an insurance market veteran of over 30 years’ leadership experience in the industry. CAREER HIGHLIGHTS • Saltus Group, Financial Advisory & Investment Management group ◦ Chair (2023 to Present) • Brown & Brown, a US listed insurance broker ◦ Director (2023-Present) • Sheriff of the City of London ◦ (2023-Present) | CURRENT DIRECTORSHIPS AND ENGAGEMENTS • Saltus Group - Chair • Brown & Brown - Director • East End Community Foundation - Chair • Alderman for the Ward of Billingsgate • Hepgtagon Assets Ltd.-Director • Bajka Investments Ltd.-Director EDUCATION • BS in Civil Engineering, University of KwaZulu Natal • MPhil. in Management Studies, University of Oxford | | | | | | CLASS II Age 62 Independent Director since March 2023 Committees • Risk and Capital Management • Investment • Governance and Nominating | | |

  7. CONTINUING DIRECTORS

    CONTINUING DIRECTORS The biographical information for the directors whose terms will continue after the Annual General Meeting and will expire at the annual general meeting to be held in 2025 (Class III) or the annual general meeting to be held in 2026 (Class I) are listed below. CLASS III DIRECTORS, SERVING IN OFFICE UNTIL THE 2025 ANNUAL GENERAL MEETING

  8. CONTINUING DIRECTORS

    | SCOTT EGAN | KEY EXPERIENCE AND QUALIFICATIONS The Board considered Mr. Egan’s over 25 years of industry experience and service as the Chief Executive Officer of Royal Sun Alliance (RSA) UK & International, and Mr. Egan’s experience as CEO of the Company, and concluded that Mr. Egan should continue to serve as a director because he brings a diverse set of skills, breadth of knowledge and valuable financial, strategic and risk management experience to our Board. CAREER HIGHLIGHTS • SiriusPoint Ltd. ◦ CEO (September 2022 to present) • Royal Sun Alliance (RSA) UK & International, a multinational general insurance company ◦ Chief Executive Officer (January 2019 to December 2021) ◦ Group Chief Financial Officer (September 2015 to December 2018) | • Towergate Insurance Limited, a European insurance intermediary ◦ Interim Chief Executive Officer and Chief Financial Officer (April 2012 to September 2015) EDUCATION • Masters Business Administration, Cranfield School of Management • Chartered Institute of Management Accountants, Member | | | | | | CLASS III Age 52 Director since September 2022 | | |

  9. CONTINUING DIRECTORS

    | RAFE DE LA GUERONNIERE | KEY EXPERIENCE AND QUALIFICATIONS The Board considered Mr. de la Gueronniere’s more than 40 years’ experience in the investment and banking industries and his qualification as an independent director and concluded that Mr. de la Gueronniere should continue to serve as a director given his deep understanding of SiriusPoint and because he brings his expertise and extensive knowledge in fixed income, equity investing and foreign exchange trading to our Board. CAREER HIGHLIGHTS • New Providence Asset Management, founded in 2003 ◦ Vice Chair and Co-Founder (2003 to 2015) • Mariner Investment Group ◦ Principal (1999 to 2003) • Discount Corporation of New York ◦ Chairman • J.P. Morgan & Co. ◦ Senior Vice President, responsible for the fixed income and precious metals businesses | • He has more than 40 years of experience in fixed income, equity investing, foreign exchange and the precious metals business PRIOR PUBLIC COMPANY BOARDS • Paine Webber, Inc., member of the Management Committee • Fusion Connect, Inc., Director PRIOR DIRECTORSHIPS AND ENGAGEMENTS • John D. and Catherine T. MacArthur Foundation, member of the Investment Committee • Taft School, Trustee and Investment Committee Chair • Far Hills Country Day School, Trustee and Investment Committee Chair • U.S. Treasury Debt Management Advisory Committee, longstanding member EDUCATION • BA in English, Brown University | | | | | | CLASS III Age 71 Independent Director since November 2013 Lead Independent Director until May 2022 Committees • Governance and Nominating • Investment | | |

  10. CONTINUING DIRECTORS

    | SHARON M. LUDLOW | KEY EXPERIENCE AND QUALIFICATIONS The Board concluded that Ms. Ludlow should continue to serve as a director because of her more than 25 years of experience in the life & health and property & casualty re-insurance industries and her qualification as an independent director and as a financial expert. CAREER HIGHLIGHTS • OMERS, one of Canada’s largest defined benefit pension plans ◦ Head of Insurance Investment Strategy (2016 to 2018) • Aviva Insurance Company of Canada ◦ President (2014 to 2016) • Swiss Re Canada ◦ President & CEO (2010 to 2014) | OTHER CURRENT PRIVATE COMPANY DIRECTORSHIPS AND ENGAGEMENTS • Green Shield Canada, Director and Chair of the Audit and Risk Committee • EIS Group, Director and Chair of the Audit Committee • Tradex/Saturn Finance Holdings Limited, Director and Chair of the Audit and Risk Committee • Lombard International Group, Director and Chair of the Audit and Risk Committee EDUCATION • Institute of Corporate Directors designation (ICD.D) • Graduate of the Corporate Directors program, Rotman School of Management, University of Toronto • Fellow Chartered Professional Accountant/Chartered Accountant (FCPA, FCA Canada) • Bachelor of Commerce, University of Toronto | | | | | | CLASS III Age 57 Independent Director since February 2021 Interim Chair of the Board since May 2022 Committees • Audit • Risk and Capital Management • Governance and Nominating | | |

  11. CONTINUING DIRECTORS

    CLASS I DIRECTORS, SERVING IN OFFICE UNTIL THE 2026 ANNUAL GENERAL MEETING

  12. CONTINUING DIRECTORS

    | FRANKLIN (TAD) MONTROSS IV | KEY EXPERIENCE AND QUALIFICATIONS The Board concluded that Mr. Montross should continue to serve as a director because of his extensive experience in the property & casualty insurance industries and his qualification as an independent director. CAREER HIGHLIGHTS • General Re Corporation ◦ Chairman and CEO (April 2009 to December 2016) ◦ Member of Gen Re’s Executive Committee and the group’s President and Chief Underwriting Officer, with responsibilities including treaty underwriting, actuarial and claims (2001) | • General Re Corporation (continued) ◦ Held a number of positions of increasing responsibility, both in the U.S. and internationally, including Chief Underwriter for the treaty business ◦ Began his career as a Casualty Facultative Underwriter (1978) EDUCATION • BA in Economics, Harvard College | | | | | | CLASS I Age 68 Independent Director since February 2021 Committees • Audit • Compensation • Risk and Capital Management | | |

  13. CONTINUING DIRECTORS

    | PETER WEI HAN TAN | KEY EXPERIENCE AND QUALIFICATIONS The Board concluded that Mr. Tan should continue to serve as a director because of his extensive investment experience working with over 40 investments in China, 12 of which eventually publicly listed on international stock exchanges. CAREER HIGHLIGHTS • Skandia Mexico & Columbia ◦ Chairman • CMIG International Holding (“CMIG International”), an investment services company ◦ Former Chairman (through December 2023) • CM Bermuda Ltd. (“CM Bermuda”), an investment services company ◦ Former Chairman (through December 2023) • IDI, Inc. ◦ Chief Executive Officer (2012) | • White & Case LLP - Attorney (2003) • Perkins Coie LLP - Attorney (1997) OTHER CURRENT DIRECTORSHIPS AND ENGAGEMENTS • Skandia Holding de Colombia, S.A., Non-Executive Director • LuxAviation Group, Director PRIOR DIRECTORSHIPS AND ENGAGEMENTS • Chongqing Zongjin Investment Co., Ltd, the financial arm of Zongshen Industrial Group, Chairman • Israel Infinity Agriculture, Director • Harbour Air, Non-executive Director • Mr. Tan formerly served on the board of multiple companies prior to their U.S. listing, including: ◦ Home Inns (NASDAQ: HMIN) ◦ E-House (NYSE: EJ) ◦ Bona Entertainment Group (NASDAQ: BONA) EDUCATION • LL.B Honors, the National University of Singapore | | | | | | CLASS I Age 51 Director since February 2021 Committees • Investment • Risk and Capital Management | | |

  14. CORPORATE GOVERNANCE FRAMEWORK

    | ● | compensation of directors, |

  15. DIRECTOR COMPENSATION

    DIRECTOR COMPENSATION COMPENSATION OF DIRECTORS FOR FISCAL YEAR 2023 The Director Compensation Policy provides for payment to each independent director of both an annual cash retainer and one or more grants of restricted shares. Annual Cash Retainer Pursuant to the terms of our Director Compensation Policy, our independent directors were entitled to receive an annual cash retainer of $137,500 per year, but with supplementary payments for independent directors in certain roles as follows:

  16. DIRECTOR COMPENSATION

    | ◦ | Lead Independent Director of the Board: $50,000; |

  17. DIRECTOR COMPENSATION

    | ◦ | Non-Executive Chair of the Board: $100,000; |

  18. DIRECTOR COMPENSATION

    | ◦ | Chairs of the Audit and Risk and Capital Management Committees: $35,000 (in the case of the Risk and Capital Management Committee, effective October 2023); and |

  19. DIRECTOR COMPENSATION

    | ◦ | Chairs of the Investment, Compensation, and Governance and Nominations Committees: $20,000 (effective October 2023). |

  20. DIRECTOR COMPENSATION

    Annual cash retainers are paid in arrears in equal quarterly installments, and are prorated for partial years of Board service based on the number of days served by the applicable independent director during any such year. Equity Incentive Grants Pursuant to the terms of the Director Compensation Policy, each independent director is entitled to receive an annual grant of restricted shares with a grant date value of $137,500 (or such higher amount as approved by the Board). Beginning in 2023, restricted share grants are typically made on or around the date of the annual general meeting of shareholders, with the number of shares being calculated based on the fair market value of a common share of the Company on the date of grant, and vest on the date of the next annual meeting of shareholders following the date of such grant, subject to the director’s continued service through such vesting date. For independent directors who join the Board after the grant date for the annual restricted share grant, but within the same year as such grant, beginning in June 2023, such directors will receive a restricted share grant equal to 50% of the annual restricted share grant for the year. Any independent directors that join the Board on or after January 1st of an applicable year and prior to the date of the annual grant will not be entitled to a pro-rated award for such period of service, but will receive their first award at the time of the next annual grant. In addition, prior to October 2023, each independent director who joined the Board received an additional initial grant of restricted shares with a grant date value of $250,000 (or such higher amount as approved by the Board), which was scheduled to vest in three equal installments on the first three anniversaries of the day the director commenced service with the Board, subject to their continued Board service through the applicable vesting date. Mr. Masojada was appointed to the Board effective as of May 2, 2023 and received an initial equity grant with a grant date fair value of $250,000. In October 2023, the Board eliminated the practice of granting an initial equity award for the first year of Board service. All restricted share grants made in 2023 were subject to the SiriusPoint Reinsurance Ltd. 2013 Omnibus Incentive Plan (the “2013 Omnibus Incentive Plan”) or, depending on the time of the effective date of the grant, the SiriusPoint Ltd. 2023 Omnibus Incentive Plan (the “2023 Omnibus Incentive Plan”) and applicable award agreements entered into between the Company and the director, including vesting and forfeiture provisions. The restricted share awards (other than initial grants of restricted shares in connection with the director’s appointment to the board) granted during 2023 are scheduled to fully vest on June 1, 2024, subject to the director’s continued Board service through the vesting date. Our directors who are not independent (including those who are our employees) do not receive compensation for serving as members of our Board. As a result, Messrs. Egan, Tan and Loeb were not compensated for their services as directors during 2023 (with the exception that Mr. Tan did receive the one-time special committee fee described below). However, all directors are reimbursed for reasonable expenses incurred in attending meetings and carrying out duties as Board and committee members, including attendance at educational seminars and other expenses directly related to the Company’s business. Special Committee Fee Following the expression of interest received from Third Point LLC in April 2023 regarding the potential acquisition of all, or substantially all, of the outstanding stock of the Company, the Board formed a special committee to consider and evaluate options for the corporate direction of the Company. All directors serving at that time, excluding Messrs. Egan and Loeb, received a one-time fee of $60,000 in compensation for the additional time commitment involved.

  21. 2023 DIRECTOR COMPENSATION

    2023 DIRECTOR COMPENSATION

  22. 2023 DIRECTOR COMPENSATION

    | | FEES EARNED OR PAID IN CASH | RESTRICTED SHARE AWARDS(1)(2) | OPTION AWARDS | ALL OTHER COMPENSATION | TOTAL | | NAME | ($) | ($) | ($) | ($) | ($) | | Rafe de la Gueronniere (3) | 202,500 | 137,500 | — | — | 340,000 | | Gretchen A. Hayes (4) | 117,731 | — | — | — | 117,731 | | Sharon M. Ludlow (5) | 448,202 | 137,500 | — | — | 585,702 | | Bronek Masojada (6) | 149,572 | 387,500 | — | — | 537,072 | | Mehdi A. Mahmud (3) | 202,500 | 137,500 | — | — | 340,000 | | Franklin (Tad) Montross IV (3) | 206,250 | 137,500 | — | — | 343,750 | | Jason Robart (3) | 202,500 | 137,500 | — | — | 340,000 | | Peter Wei Han Tan (7) | 60,000 | — | — | — | 60,000 | | Daniel S. Loeb | — | — | — | — | — |

  23. 2023 DIRECTOR COMPENSATION

    | (1) The restricted shares were awarded to the independent directors on June 15, 2023 under our 2023 Omnibus Incentive Plan. Restricted shares awarded on June 15, 2023 will vest on June 1, 2024, subject to the director’s continued service through such date. In addition, Mr. Masojada was awarded additional restricted shares on May 8, 2023 under our 2013 Omnibus Incentive Plan, with a |

  24. 2023 DIRECTOR COMPENSATION

    grant date fair value of $250,000 in connection with his appointment to the Board. As of December 31, 2023, our non-employee directors during 2023 had the following number of outstanding restricted shares:

  25. 2023 DIRECTOR COMPENSATION

    | NAME | NUMBER OF UNVESTED RESTRICTED SHARES | NAME | NUMBER OF UNVESTED RESTRICTED SHARES | | Rafe de la Gueronniere | 22,865 | Franklin (Tad) Montross IV | 22,865 | | Gretchen A. Hayes | 7,936 | Jason Robart | 38,304 | | Sharon M. Ludlow | 22,865 | Peter Wei Han Tan | — | | Mehdi A. Mahmud | 22,865 | Daniel S. Loeb | — | | Bronek Masojada | 41,840 | | |

  26. 2023 DIRECTOR COMPENSATION

    | (2) The amounts reported in this column are valued based on the aggregate grant date fair value computed in accordance with FASB ASC Topic 718, modified to exclude the effect of estimated forfeitures. The fair value was determined using the methodology and assumptions set forth in Note 18, “Share-Based Compensation and employee benefit plans,” to the Audited Consolidated Financial Statements included in our Annual Report on Form 10-K for the year ended December 31, 2023, which are hereby incorporated herein by reference. |

  27. 2023 DIRECTOR COMPENSATION

    | (3) Messrs. Gueronniere, Mahmud, Montross IV and Robart each received a base fee of $137,500, the special committee fee of $60,000, and a pro-rated supplemental fee for each such director as a result of their service as Chairs of the Investment, Governance and Nominations, Risk and Capital Management, and Compensation Committees, respectively, for the period from October through December of 2023. |

  28. 2023 DIRECTOR COMPENSATION

    | (4) Reflects prorated fees earned from January 1, 2023 through June 1, 2023, the effective date of Ms. Hayes’s resignation from our Board, as well as the special committee fee of $60,000. |

  29. 2023 DIRECTOR COMPENSATION

    | (5) Ms. Ludlow received a base fee of $137,500. In addition, Ms. Ludlow received additional fees approved by the Board for additional services in the year in order to take into account the extent of the changes being undertaken by the Company during this period. These fees included a fee for services as Interim Chair for the period between January 1, 2023 and May 31, 2023 of $146,952, a fee for services as Audit Committee Chair for the period between January 1, 2023 and June 2023 of $86,250 and from July to December of 2023 of $17,500, and the special committee fee of $60,000. |

  30. 2023 DIRECTOR COMPENSATION

    | (6) Reflects prorated fees earned from May 2, 2023, the effective date of Mr. Masojada’s appointment to our Board through December 31, 2023, as well as the special committee fee of $60,000, and a pro-rated supplementary fee payment as result of his appointment as non-executive Chair of the Board effective as of June 1, 2023. |

  31. 2023 DIRECTOR COMPENSATION

    | (7) Mr. Tan does not receive regular director fees. However, he did receive the $60,000 special committee fee. |

  32. 2023 DIRECTOR COMPENSATION

    | EXECUTIVE OFFICERS |

  33. 2023 DIRECTOR COMPENSATION

    The following table sets forth information regarding the individuals who serve as our executive officers.

  34. 2023 DIRECTOR COMPENSATION

    | NAME | AGE | POSITION | | Scott Egan | 52 | Chief Executive Officer & Director | | Stephen Yendall | 48 | Chief Financial Officer | | David E. Govrin | 60 | Group President and Chief Underwriting Officer | | Robin Gibbs | 49 | Chief Executive Officer, SiriusPoint International |

  35. 2023 DIRECTOR COMPENSATION

    | SCOTT EGAN | KEY EXPERIENCE AND QUALIFICATIONS The Board considered Mr. Egan’s over 25 years of industry experience and service as the Chief Executive Officer of Royal Sun Alliance (RSA) UK & International, and Mr. Egan’s experience as CEO of the Company, and concluded that Mr. Egan should continue to serve as a director because he brings a diverse set of skills, breadth of knowledge and valuable financial, strategic and risk management experience to our Board. CAREER HIGHLIGHTS • SiriusPoint Ltd. ◦ CEO (September 21, 2022 to present) • Royal Sun Alliance (RSA) UK & International, a multinational general insurance company ◦ Chief Executive Officer (January 2019 to December 2021) ◦ Group Chief Financial Officer (September 2015 to December 2018) | • Towergate Insurance Limited, a European insurance intermediary ◦ Interim Chief Executive Officer and Chief Financial Officer (April 2012 to September 2015) EDUCATION • Masters Business Administration, Cranfield School of Management • Chartered Institute of Management Accountants, Member | | | | | | Chief Executive Officer since 2022 Age 52 | | |

  36. 2023 DIRECTOR COMPENSATION

    | STEPHEN YENDALL | CAREER HIGHLIGHTS • SiriusPoint Ltd. ◦ Chief Financial Officer (October 2022 to present) • Guy Carpenter Inc., a company providing global risk and reinsurance solutions and a subsidiary of Marsh & McLennan Companies, Inc. ◦ Managing Director (October 2021 to October 2022) • RSA Canada Group, a Canadian general insurer ◦ Chief Financial Officer and Chief Operating Officer (August 2018 to October 2021) • Ernst & Young LLP, a public accounting firm ◦ Partner (June 2016 to August 2018) | EDUCATION • BA, University of Waterloo | | | | | | Chief Financial Officer since October 2022 Age 48 | | |

  37. 2023 DIRECTOR COMPENSATION

    | DAVID E. GOVRIN | CAREER HIGHLIGHTS • SiriusPoint Ltd. ◦ Global Chief Underwriting Officer and President, Americas Reinsurance (March 2021 to present) • Third Point Reinsurance (USA) Ltd. ◦ President (May 2019 to March 2021) ◦ Head of Business Development (February 2019 to 2021) • Berkshire Hathaway’s Reinsurance Group, a reinsurance company ◦ Vice President and key member of the underwriting team (2012 to 2019) • Hudson Insurance Capital Partners, a specialty insurance focused private equity fund of approximately $200 million ◦ Founder (2007) • Sierra Re Advisors, a boutique reinsurance intermediary ◦ Founder (2006) • Ritchie Capital Management, an alternative asset manager ◦ Managing Director/ILS Fund Manager (2005 to 2006) | • Citigroup ◦ Director, Structured Insurance Products group (2002 to 2004) • Goldman Sachs ◦ Vice President, Initial member of the Insurance Products Group developing the ILS market (1997 to 2002) • Guy Carpenter ◦ Senior Vice President, property account executive executing and developing traditional, structured, and capital markets products (1989 to 1997) • Dean Witter Reynolds ◦ Fixed income operations, sales and trading (1986 to 1989) • Horizon Bank ◦ Commercial Credit Analyst (1985 to 1986) EDUCATION • Master of Business Administration in Finance, NYU’s Stern School of Business • Bachelor of Science in Finance and Real Estate, University of Denver | | | | | | Global Chief Underwriting Officer and President, Americas Reinsurance since March 2021 Age 60 | | |

  38. 2023 DIRECTOR COMPENSATION

    | ROBIN GIBBS | CAREER HIGHLIGHTS • SiriusPoint Ltd. ◦ Chief Executive Officer, SiriusPoint International (December 2022 to present) • RSA Insurance Group, a British multinational general insurance company ◦ Commercial Managing Director, Commercial Risk Solutions Managing Director, Mobility Insurance Managing Director, Director of Regions, Delegated Business Managing Director, Interim Mid-Market Managing Director, Strategy Director, Head of Underwriting, New Business Manager (September 2001 to December 2022) | EDUCATION • Bachelor’s Degree, Aston Business School | | | | | | Chief Executive Officer, SiriusPoint International since December 2022 Age 49 | | |

  39. 2023 DIRECTOR COMPENSATION

    | EXECUTIVE COMPENSATION |

  40. 2023 DIRECTOR COMPENSATION

    | PROPOSAL 2 | ADVISORY VOTE TO APPROVE NAMED EXECUTIVE OFFICER COMPENSATION (SAYON-PAY) | | TO APPROVE, BY A NON-BINDING ADVISORY VOTE, THE EXECUTIVE COMPENSATION PAYABLE TO THE COMPANY’S NAMED EXECUTIVE OFFICERS AS DESCRIBED IN THIS PROXY STATEMENT | |

  41. 2023 DIRECTOR COMPENSATION

    As a result of the Dodd-Frank Wall Street Reform and Consumer Protection Act, and in accordance with Section 14A of the Exchange Act, the Company’s shareholders are entitled to approve, on an advisory basis, the compensation of our named executive officers (“NEOs”). This non-binding advisory vote, commonly known as a “Say-on-Pay” vote, gives our shareholders the opportunity to express their views on our NEOs’ compensation. This vote is not intended to address any specific item of compensation but rather the overall compensation of our NEOs and the philosophy, policies and practices described in this proxy statement. As described in detail under “Compensation Discussion and Analysis,” our compensation programs are designed to

  42. 2023 DIRECTOR COMPENSATION

    | • | attract, motivate and retain executives of outstanding ability to meet and exceed the demands of our business, |

  43. 2023 DIRECTOR COMPENSATION

    | • | focus management on optimizing shareholder value and fostering an ownership culture, |

  44. 2023 DIRECTOR COMPENSATION

    | • | create appropriate rewards for outstanding performance and reduced compensation for underperformance, and |

  45. 2023 DIRECTOR COMPENSATION

    | • | be competitive and foster collaboration by rewarding executives for their contribution to our overall performance and financial success. |

  46. 2023 DIRECTOR COMPENSATION

    We believe our compensation program is effective, appropriate and strongly aligned with the long-term interests of our shareholders and that the total compensation packages provided to our NEOs are reasonable and not excessive. For these reasons, the Board is asking shareholders to vote “FOR” the following resolution: “RESOLVED, that the compensation paid to the Company’s named executive officers, as disclosed pursuant to the rules of the Securities and Exchange Commission, including the Compensation Discussion and Analysis, compensation tables and narrative discussion, is hereby APPROVED.” As an advisory vote, this Proposal 2 is not binding on the Board or the Compensation Committee (or any other committee of the Board), will not overrule any decisions made by the Board or the Compensation Committee (or any other committee of the Board) and will not require the Board or the Compensation Committee (or any other committee of the Board) to take any specific action. The outcome of this vote does not create or imply any change to the fiduciary duties of the Company or its Board or any of its committees (or any individual member thereof), or create or imply any additional fiduciary duties. Although the vote is non-binding, the Board and the Compensation Committee value the opinions of our shareholders, and will carefully consider the outcome of the vote when making future compensation decisions for our NEOs.

  47. SiriusPoint’s 2023 Compensation Highlights

    | ● | The short-term incentive plan was made up of two components: Core Combined Ratio (70%) and Strategic Objectives (30%). Importantly, nothing could become payable under this plan unless a threshold of Core Combined Ratio performance was delivered. This was designed to support the delivery of the ‘underwriting-first’ strategy that had been developed to clearly focus the business on underwriting results. |

  48. SiriusPoint’s 2023 Compensation Highlights

    | ● | The long-term incentive plan was made up of a combination of performance-based restricted stock unit (PSU) (75%) and time-based restricted stock unit (RSU) (25%) components. The PSU component is 100% driven by growth of net book value per share over a compound 3-year period and the RSU was designed as a retentive factor alongside the performance driven factor. |

  49. SUMMARY OF OUR EXECUTIVE COMPENSATION PRACTICES

    | WHAT WE DO | | WHAT WE DON’T DO | | | | We focus on attracting and retaining superior and diverse executive talent | | We do not award stock options with an exercise price below 100% of fair market value | | | We require officers and directors to satisfy meaningful share ownership requirements | | We do not allow our directors, executive officers, employees and their related persons to pledge the Company’s securities as collateral for loans or for any other purpose | | | We seek to mitigate undue risk in compensation programs through informed performance goal-setting that considers multiple financial and non-financial factors | | We do not allow our directors, executive officers, employees and their related persons to hedge the Company’s securities | | | Our Compensation Committee retains the services of an independent compensation consultant | | We do not provide “gross-ups” for golden parachute taxes | | | We generally consider market and industry data when setting executive pay, using the median as a reference point to understand the general market | | We do not reprice stock options unless approved in advance by our shareholders | | | We maintain a clawback policy applicable to executive officers in the event of a financial statement restatement, and, in January 2024, expanded this to allow recoupment for serious/gross misconduct | | We do not incentivize excessive risk-taking through our compensation programs, and a review of risk events forms part of the Compensation Committee’s considerations when making award decisions | | | We offer double-trigger change-in-control benefits | | |

  50. PAY-FOR-PERFORMANCE ALIGNMENT

    | ● | Long-term incentives were granted in 2023 in the form of PSUs, where vesting is contingent on company performance measures being achieved (75% weighting) and RSUs where vesting is subject to continued service (25% weighting). The target LTI opportunities for the NEOs reflect market practice, their experience and performance, retention considerations, and their employment agreements. |

  51. PAY-FOR-PERFORMANCE ALIGNMENT

    | ● | In light of the financial results outlined above, the Committee determined that the continuing NEOs would receive short-term incentive awards paid at 165% of target in respect of 2023. |

  52. Results of Say-on-Pay Vote

    Results of Say-on-Pay Vote The Compensation Committee considers the outcome of the annual shareholder advisory vote on executive compensation when making decisions relating to the compensation of our NEOs and our executive compensation program generally. At our 2023 annual general meeting of shareholders, our shareholders approved the compensation paid to our then-serving NEOs in a non-binding advisory vote. Approximately 73% of the shareholders who voted on the proposal voted in favor of the proposal. The 2023 say-on-pay vote related to compensation paid to NEOs during 2022. The Company reviewed feedback provided by Institutional Shareholder Services, and also solicited feedback from Messrs. Tan and Loeb (who, in addition to serving as members of our Board, are the Company’s two largest shareholders) to get a better understating of the say-on-pay voting results, and found that concerns related primarily to terms of the previous CEO’s departure, and the level of executive compensation in relation to performance. Given the appointment of new leadership at the end of 2022, the Compensation Committee had already begun to review the executive compensation program in November 2022, and put in place revised compensation programs in early 2023 which reflected changes to better align with shareholder interests, including as outlined above: (i) a revised short term incentive scheme aligned to Core Combined Ratio performance and in which zero payment will be made on any element of the plan until a threshold of Core Combined Ratio performance has been delivered, (ii) granting PSUs which are scheduled to vest based on our growth in the net book value per share over a three-year period and (iii) eliminating stock options from the 2023 long-term incentive program. The Committee reviewed the say-on-pay results carefully, and after considering the shareholder support for the turnaround and the fact that significant positive changes had already been made to the Company’s executive compensation program, it concluded that it was not necessary to make further direct changes in response to the 2023 say-on-pay vote. However, for 2024, the Compensation Committee has reviewed the annual and long-term incentive financial targets and approved the use of increased targets under the 2024 compensation program in order to reflect the turnaround progress of the Company and its forward-looking plans, as well as to incorporate targets that are designed to be challenging, but achievable with strong performance.

  53. Results of Say-on-Pay Vote

    | EVALUATE | | APPROVE | | | • | Market data from independent compensation consultant | • | Company performance metrics for annual and long-term compensation, and specific targets, thresholds and maximums for each measure | | • | Peer group composition | • | Individual performance goals for NEOs | | • | Ability of compensation program to attract and retain superior talent | • | Achievement of performance metrics for annual incentive plan and long-term incentive plan | | • | Alignment of performance measures with overall strategy | • | Salary, benefits and target annual and long-term incentive compensation levels for NEOs | | • | Feedback from annual-say-on-pay vote | | | | DISCUSS | | | | | • | Progress against financial and strategic goals | | | | • | Report from Chief Risk Officer on any material risk items, to inform incentive award decisions | | | | • | Risk assessment of executive compensation program | | | | • | Market and governance practices | | |

  54. Results of Say-on-Pay Vote

    | ● | Provide compensation and benefits packages that are competitive with other peer companies operating in the reinsurance and insurance industry; |

  55. Results of Say-on-Pay Vote

    | ● | Focus on long-term performance to support shareholder value creation and retain executives. |

  56. Results of Say-on-Pay Vote

    | V. | PEER GROUP |

  57. Results of Say-on-Pay Vote

    The Compensation Committee uses a peer group to evaluate executive compensation decisions. The Compensation Committee believes that the Company’s peer group should reflect the markets in which the Company competes for business, executive talent and capital. Accordingly, the peer group includes companies meeting one or more of the following peer group selection criteria:

  58. Results of Say-on-Pay Vote

    In May 2022, the Compensation Committee approved an updated peer group to better reflect the Company’s competitive compensation market following the merger of Third Point Reinsurance Ltd. and Sirius International Insurance Group, Ltd. Utilizing the peer group selection criteria described above and considering the availability of disclosure data for benchmarking purposes, five new peers were added to the Company’s peer group (Markel Corporation, W.R. Berkley Corporation, The Hanover Insurance Group, Inc., Selective Insurance Group, Inc. and Employers Holdings, Inc.) while three peers were removed (Beazley plc, Lancashire Holdings Limited, and Greenlight Capital Re, Ltd.). This peer group was used to determine the initial compensation of the CEO and Chief Financial Officer in 2022 and the compensation for each of the NEOs during 2023. The compensation peer group consisted of the following companies:

  59. Results of Say-on-Pay Vote

    | ● Argo Group International Holdings Ltd. | ● The Hanover Insurance Group, Inc. | | ● RenaissanceRe Holdings Ltd. | | ● Axis Capital Holdings Ltd. | ● Hiscox Ltd. | | ● RLI Corp. | | ● Employers Holdings, Inc. | ● James River Group Holdings, Ltd. | | ● Selective Insurance Group, Inc. | | ● Enstar Group Limited | ● Markel Corporation | | ● White Mountains Insurance Group Ltd. | | ● Global Indemnity Limited | ● ProAssurance Corporation | | ● W.R. Berkley Corporation | | Our assets, revenue, and market capitalization compared to our peer group were as follows: | | | | | | ASSETS (1) | REVENUES (1) | MARKET CAPITALIZATION(2) | | SiriusPoint | $12,872 | $2,737 | $1,944 | | Relative Peer Group Position: 2023 Peer Group (3) | 56th percentile | 51st percentile | 29th percentile |

  60. Results of Say-on-Pay Vote

    | (3) Relative peer group positioning excludes Argo Group International Holdings Ltd., which was acquired by Brookfield Reinsurance in November 2023. |

  61. Results of Say-on-Pay Vote

    | ● | annual cash incentive compensation; |

  62. Results of Say-on-Pay Vote

    | ● | long-term incentive compensation; |

  63. Results of Say-on-Pay Vote

    | | | ELEMENT | PURPOSE | | FIXED | | BASE SALARY | ● To provide base compensation for executives’ ongoing performance of job responsibilities throughout the year. ● To attract and retain executives with the knowledge, skills and abilities necessary to successfully execute their job responsibilities. ● To recognize each executive’s position, role, responsibility and experience. ● To remain competitive in the industry. | | VARIABLE | Short-term | ANNUAL CASH INCENTIVE | ● To focus executive officers on achieving the annual goals of the Company by paying rewards to the extent the goals are fulfilled. ● To recognize how individuals have performed in meeting their established goals for the year. ● To reward exceptional performance through increased cash incentive payouts (subject to the overall annual cash incentive pool), and lower payouts where individual performance is below expectations. | | | Long-term | EQUITY AWARDS | ● To align the interests of employees with shareholders through meaningful equity participation and long-term ownership. ● To promote the long-term retention of our executives. | | ADDITIONAL BENEFITS | | Retirement, Health and Welfare Benefits | ● To provide executives with an opportunity to save for retirement. ● To help ensure that we have productive and focused executives through reliable and competitive health and other benefits. | | | Benefits | Perquisites (for certain employees working outside of their home country) | ● To attract and retain key employees in Bermuda (in line with typical insurance/reinsurance industry and Bermuda-based company practice). ● To rationalize the income of expatriate employees, who experience additional taxation as a result of compensation for additional housing and transportation expenses, with the income that such employees would earn as employees within their native countries. |

  64. Results of Say-on-Pay Vote

    | VIII. | ANNUAL CASH INCENTIVE PAY |

  65. Results of Say-on-Pay Vote

    The purpose of annual cash incentive pay is to reward performance during the year based upon the achievement of business and individual goals. Performance metrics are set based on the measures that the Compensation Committee deems necessary to achieve operational success. The performance metrics are periodically reviewed and adjusted, where required, in the Compensation Committee’s judgment. The annual cash incentive plan formula (described below) creates a cash incentive pool but does not determine individual awards. An individual award from the 2023 cash incentive pool was paid to Mr. Egan, our CEO, based upon the Compensation Committee’s evaluation of his performance compared to previously established goals and objectives. For all other then-serving NEOs, award payouts were recommended to the Compensation Committee by the CEO based on how each executive performed relative to his or her individual annual goals.

  66. Annual Cash Incentive Plan for 2023

    Annual Cash Incentive Plan for 2023 Each of the NEOs, other than Mr. Liddell, participated in our 2023 annual cash incentive plan (the “Annual Incentive Plan”). Under the Annual Incentive Plan, the total annual cash incentive pool was calculated by applying the actual result of the financial metric, weighted at 70%, and the actual result of the strategic metrics, weighted at 30%. The financial and strategic metrics for the Annual Incentive Plan for 2023 were intended to motivate continued progress with the turnaround of the business. For 2023, the Compensation Committee transitioned from using three financial performance metrics (Net Services Fee Income, Services Fee Revenue and Core Combined Ratio) to one financial performance metric (Core Combined Ratio) in order to incentivize all leaders and colleagues to focus on profitability and the achievement of a shared goal. The Compensation Committee selected Core Combined Ratio as the sole financial performance metric under the Annual Incentive Plan because the Compensation Committee believes it effectively measures the profitability of the Company’s business and the metric is commonly used by industry peer companies to measure performance and the value created through effective underwriting. The 2023 Core Combined Ratio goal was designed to be challenging but achievable with strong management performance. The strategic objectives, which are described in further detail in the table below and which made up the remaining 30% incentive pool funding, were deemed critical to establishing a strong foundation for the future direction and operation of the Company. The Core Combined Ratio financial performance metric had a potential performance range of 50% at threshold to 200% at maximum for its 70% contribution (with no payout below threshold). The strategic objectives had a potential performance range of 0% to 100% of target for their 30% weighting (with no payouts if the Core Combined Ratio financial performance metric was below threshold). As a result, the maximum funding level of the Annual Incentive Plan was 170% of the aggregate target bonus amounts for all participants in the Annual Incentive Plan. The individual Annual Incentive Plan payments to the NEOs were determined by the Compensation Committee based on the target annual cash incentive opportunity for each applicable NEO and the amount of the overall annual cash incentive pool. These amounts could then be modified by the application of business unit/function and individual performance modifiers (as determined in the discretion of the Compensation Committee and the CEO based upon individualized performance goals set for each such NEO by the Compensation Committee in March 2023).

  67. Annual Cash Incentive Plan for 2023

    | 2023 Annual Cash Incentive Metrics | | | | | | | | | Annual Cash Incentive Performance Metrics | Threshold | Target | Maximum | Actual Result | Actual Payout as a % of Target | Weight | Bonus Pool Funding | | Core Combined Ratio (1) | >96.7% 50% payout (0% if greater than 96.7%) | 95.7% 100% payout if at target | <=92.7% 200% payout if equal to this target or lower | 89.1% | 200% | 70% | 165% | | Strategic Goals | Not Met/Partial 0/50% payout cliff | | Fully Achieved 100% payout | See narrative below | 83% | 30% | |

  68. Annual Cash Incentive Plan for 2023

    | (1) Core Combined Ratio includes the sum of core loss and loss adjustment expenses incurred, net, acquisition costs, net and other underwriting expenses divided by core net premiums earned. |

  69. Annual Cash Incentive Plan for 2023

    In February 2024, the Compensation Committee reviewed the Company’s performance for the 2023 fiscal year, and determined that the Company’s Core Combined Ratio was 89.1%, resulting in a payout factor of 200% of target for the financial performance goal. The Compensation Committee also assessed the Company’s progress with respect to the six Company-wide strategic objectives approved in March 2023. Within each area, potential actions were identified for management to pursue. In February 2024, the Compensation Committee assessed performance as summarized below. Based on this discussion, the Compensation Committee determined that the strategic goals metric was achieved at 83% of target.

  70. Annual Cash Incentive Plan for 2023

    | Strategic Objective | Achievements | | Simplify the business and build a high-performance culture. | ● Carried out a full review of the structure and operating model to enable a high performing culture with a clear global focus, clear remit scopes, and clarity of accountabilities and reporting lines. ● Progressed the embedding of a high-performing, merged ‘SiriusPoint’ business culture to support the focus on collaboration, cost, and continuous improvement. ● Accident and Health rationalization completed. ● Focus on risk continued through initiation and progression of anchor projects. | | Reduce the Company’s cost base by $30 million. | ● Reduced cost base by $50 million through a combination of delivery of continued international transformation, overall business simplification, and a line-by-line review of all cost items. | | Deliver returns on tangible equity (ROTE) of approximately 11% in 2023. | ● ROTE 20%.(1) | | Rationalize the Company’s strategic partnerships, including delivering $700 million of premiums through consolidated MGAs and $1.5 billion in premiums from all MGAs. | ● $683 million of consolidated MGA premiums delivered; and $1.49 billion of premiums delivered taking into account all MGAs. Evaluating relationships to identify optimum distribution/relationship strategy and to raise capital and deliver against agreed plan. | | Continue reducing volatility in the business. | ● Continued to make progress reducing volatility through a combination of continued de-risking of CAT exposure and reducing volatility in investments. | | Improve capital modelling and reduce capital risk via capital raising measures. | ● Capital modelling done, and 2023 LPT delivered, with further actions planned for 2024. |

  71. Annual Cash Incentive Plan for 2023

    (1) “ROTE” refers to return on tangible equity and is calculated as the Company’s net income for the period over the average tangible equity available to common shareholders. The Compensation Committee also reviewed performance by each of the applicable NEOs against the business unit/function and individualized goals set for each such NEO in March 2023. In light of the consistent performance, and the collective effort of the executive team in achieving the Company’s strategic objectives, the Compensation Committee determined not to apply any business unit/function or individual performance modifier to the awards for any of the NEOs with respect to the 2023 Annual Incentive Plan. The Compensation Committee also considered a report from the Chief Risk Officer to consider if any downward adjustment to the funding or individual awards should be made for risk-related items. After considering the Chief Risk Officer’s report, the Compensation Committee concluded that the scoring of the components of the plan were appropriate, and there were no factors that warranted adjustment for risk-related items. As a result, each NEO (other than Mr. Liddell) received an award under the 2023 Annual Incentive Plan equal to 165% of the NEO’s target annual cash incentive opportunity. The chart below sets forth our participating NEOs’ target annual cash incentive opportunities under the Annual Incentive Plan and the actual cash incentive paid to each such NEO who was entitled to receive a bonus payment under the Annual Incentive Plan for fiscal year 2023. For 2023, each of these NEOs had an annual cash incentive target opportunity that was expressed as a percentage of the NEO’s year-end base salary. The annual cash incentive target opportunities were determined by the Compensation Committee based on seniority, role and responsibilities within the Company, experience level, and competitive market data.

  72. Annual Cash Incentive Plan for 2023

    | | TARGET ANNUAL CASH INCENTIVE OPPORTUNITY | | ACTUAL ANNUAL INCENTIVE PAID | | | NEO | % OF BASE SALARY | ($) | AS A % OF TARGET ANNUAL CASH | ($) | | Scott Egan(1) | 140% | 1,540,000 | 165% | 2,541,000 | | Stephen Yendall(1) | 100% | 515,932 | 165% | 851,288 | | David E. Govrin | 100% | 650,000 | 165% | 1,072,500 | | Rob Gibbs (1) | 100% | 477,506 | 165% | 787,885 |

  73. Annual Cash Incentive Plan for 2023

    | (1) For 2023, pursuant to the terms of their offer letters and as an inducement for each to accept employment with the Company, Messrs. Egan, Yendall and Gibbs were each eligible to receive guaranteed bonuses equal to 100% of their targets. However, the performance outcome of the Annual Incentive Plan was greater than this amount, and so the awards are fully earned on performance relative to the targets set. In line with reporting requirements, the guaranteed portion of the bonuses paid to Messrs. Egan, Yendall and Gibbs are reported in the “Bonus” column of the “2023 Summary Compensation Table” while the remaining portion is shown under the “Non-Equity Incentive Plan Compensation” column. |

  74. Additional Cash Bonus Arrangements

    Additional Cash Bonus Arrangements From time to time we provide sign-on grants to attract and retain superior executive talent and to compensate such executives for compensation that was forfeited with their prior employer in connection with joining SiriusPoint. As disclosed in last year’s report, in 2022, we awarded Mr. Yendall a one-time $320,000 Canadian dollars sign-on bonus upon commencement of his employment with the Company to recognize his loss of income from changing employers, which became payable in March 2023 under the terms of his offer of employment (in US dollars. The total value of this bonus when paid was $236,302 using the December 31, 2022 currency spot rate of 0.7384). Pursuant to an annual incentive agreement dated as of March 1, 2012 (as amended from time to time), Mr. Liddell’s annual cash incentive award opportunity was equal to five percent (5%) of global A&H technical underwriting profits over successive three-year rolling periods, capped at 3.5 times his base salary as of the end of the final financial year. However, Mr Liddell left the company effective July, 12, 2023, and no incentive payment was made in respect of 2023.

  75. Additional Cash Bonus Arrangements

    | IX. | LONG-TERM INCENTIVES |

  76. Additional Cash Bonus Arrangements

    The purpose of long-term incentives is to align the interests of employees with those of shareholders through meaningful equity participation. The program can generate significant value when executives drive the Company to achieve long-term results. The following principles govern our long-term incentive program:

  77. Additional Cash Bonus Arrangements

    | ● | Long-term incentives aim to provide balance to a short-term performance focus. Executives should be focused on achievement of the Company’s long-term strategic objectives. Through long-term incentives, we encourage executives to drive strong Company performance over the long term. |

  78. Additional Cash Bonus Arrangements

    | ● | Long-term incentive awards should reflect market-competitive compensation levels. Individual grants vary based on individual performance, which reward individual achievement as well as long-term corporate performance. |

  79. Additional Cash Bonus Arrangements

    | ● | The mix of long-term incentives will vary by role and level in the Company to balance retention, the drive for long-term growth in shareholder value and the individual’s ability to contribute to value creation. |

  80. Additional Cash Bonus Arrangements

    | ● | The Company may use a variety of incentive awards from year to year to deliver long-term incentives. |

  81. Additional Cash Bonus Arrangements

    | ● | Our long-term incentive program provides for annual long-term incentive grants with overlapping vesting schedules and performance cycles to incentivize and promote retention of employees and executives. |

  82. Long-Term Incentives Awarded in 2023

    Long-Term Incentives Awarded in 2023 In 2023, the Compensation Committee granted long-term incentives under the 2013 Omnibus Incentive Plan under the program design described below to each of our NEOs. In 2022, the Compensation Committee temporarily changed the long-term incentive mix from the mix used in 2021, which was delivered in the form of performance-based restricted share units, time-based restricted units and options in order to retain key employees during a time of significant change at the Company, and delivered the mix in a combination of time-based restricted units and stock options. For 2023, the Compensation Committee reverted to its prior practice of using performance-based restricted share units (PSUs), and granted 75% of each NEO’s long-term incentive opportunity in the form of PSUs, with the remaining 25% of each NEO’s long-term incentive opportunity granted in the form of time-based restricted units (RSUs). The Compensation Committee designed the long-term incentive award for 2023 to achieve various objectives:

  83. Long-Term Incentives Awarded in 2023

    | ● | provide substantial at-risk compensation to our NEOs in order to align their interests with shareholders and the Company’s performance, with the value of the awards fluctuating based on the Company’s stock price performance; | | ● | incentivize them to grow the Company; and | | ● | retain them during the essential turnaround period. |

  84. Long-Term Incentives Awarded in 2023

    | Element | Key Metrics | Features | | PSUs | ● Vesting subject to the achievement of targets based on the Compound annual growth rate of the Company’s tangible net book value per share (“NBVPS”) between December 31, 2022 and December 21, 2025, and continued service | ● Provides alignment with shareholders ● 3-year cliff vesting period ● Fosters retention | | RSUs | ● Vesting subject to continued service over a 3-year period following the grant date | ● Provides alignment with shareholders ● 3-year tranche vesting period (vests in equal tranches after years 1, 2 and 3) ● Fosters retention |

  85. 2023 PSUs

    2023 PSUs In 2023, PSUs were granted subject to cliff-vesting at the end of a three-year performance period (beginning December 31, 2022 and ending December 31, 2025) based upon compound annual growth rate of the Company’s tangible NBVPS during the performance period, as set forth below:

  86. 2023 PSUs

    | 2023-25 PSUs | Below “Threshold” Levels of Performance | “Threshold” Levels of Performance | “Target” Levels of Performance | “Maximum” Levels of Performance | | Compound Annualized Growth Rate in tangible NBVPS(1) | below 6% | 6% | 8% | 10% | | Vesting level (% of target opportunity)(2) | Nil | 50% | 100% | 200% |

  87. 2023 PSUs

    | (1) Tangible NBVPS compound annualized growth rate will be calculated subject to standard adjustments for currency and exchange rates, accounting changes, and dividend and capital payments, and also excludes certain selected legacy investments disposed of by the Company prior to December 31, 2024. |

  88. 2023 PSUs

    | (2) For performance between the levels shown in the table, the vesting level will be determined using linear interpolation. |

  89. 2023 PSUs

    The Compensation Committee determined to award long-term incentives in the form of PSUs in order to align with market practice and to create a more direct alignment between pay and performance.

  90. 2023 RSUs

    2023 RSUs The Compensation Committee believes that time-based restricted share units (RSUs) align the interests of our NEOs with the interests of our shareholders through the Company’s share price performance and also fosters retention of our NEOs as they vest ratably over a three-year period. Time-vesting restricted share units granted to our NEOs in April 2023 will vest in equal annual installments on the first three anniversaries of the grant date, subject to each NEO’s continued employment through each vesting date, with the last one-third of such awards becoming fully vested in April 2026.

  91. 2023 TARGET LONG-TERM INCENTIVE AWARD OPPORTUNITIES

    2023 TARGET LONG-TERM INCENTIVE AWARD OPPORTUNITIES The Compensation Committee established the 2023 target long-term award opportunity for each of the NEOs after considering:

  92. 2023 TARGET LONG-TERM INCENTIVE AWARD OPPORTUNITIES

    | ● | A competitive market analysis of each NEO’s total compensation and the portion of total compensation provided as long-term incentives, relative to similar roles at companies in our Peer Group; | | ● | The Company’s and each NEO’s individual performance and his or her expected future contributions; | | ● | The NEO’s level of experience in his or her role; and | | ● | Retention considerations. |

  93. 2023 TARGET LONG-TERM INCENTIVE AWARD OPPORTUNITIES

    In addition, in the cases of Messrs. Egan, Yendall and Gibbs, their target incentive opportunities were established at the time they joined the Company, with the level determined based on the competitive market and in order to induce each to join the Company. In the case of Mr. Govrin, his target opportunity was established at the time of his promotion to the position of Group President & Chief Underwriting Officer of the Company and SiriusPoint America Insurance Company, considering the market data and the increased scope of his role. Awards under our long-term incentive program which were made to our NEOs in April 2023, are reflected in the table below.

  94. 2023 TARGET LONG-TERM INCENTIVE AWARD OPPORTUNITIES

    | NEO | 2023 Total Grant Value | Number of Units Granted in April 2023 | | | | ($) | RSUs | PSUs (at target) | | Scott Egan | 4,889,402 | 129,349 | 388,048 | | Stephen Yendall | 1,224,087 | 32,383 | 97,150 | | David E. Govrin (1) | 1,989,149 | 52,623 | 157,869 | | Rob Gibbs | 970,128 | 25,665 | 76,994 | | Stuart Liddell (2) | 303,449 | 8,028 | 24,083 |

  95. 2023 TARGET LONG-TERM INCENTIVE AWARD OPPORTUNITIES

    | (1) Due to additional responsibilities with his appointment as Group President and Chief Underwriting Officer of the Company, effective as of November 2022, Mr. Govrin’s long-term incentive award was increased compared to 2022 (total grant value $783,749). |

  96. 2023 TARGET LONG-TERM INCENTIVE AWARD OPPORTUNITIES

    | (2) Mr Liddell’s awards that were granted in 2023 lapsed on his leaving the company, effective July 12, 2023. |

  97. 2023 TARGET LONG-TERM INCENTIVE AWARD OPPORTUNITIES

    In February 2024, the Compensation Committee approved the grant of 2024 annual long-term incentive awards for NEOs and other critical leaders to be delivered 25% in the form of RSUs and 75% in the form of PSUs, with vesting based upon three-year tangible net book value per share performance.

  98. 2021-2023 PSUs

    2021-2023 PSUs In 2021, the Compensation Committee granted PSUs to the Company’s then-serving executives, including Mr. Govrin. For the PSUs granted in April 2021, the Compensation Committee established Tangible Book Value Per Share Growth (“TBVPS Growth”) as the sole metric for the 34-month performance period beginning February 26, 2021 and ending December 31, 2023. The vesting of the 2021 PSUs was also subject to the recipient’s continued employment through the vesting date in April 2024. Under the terms of the award agreements, TBVPS Growth is calculated by taking common shareholders’ equity, less intangible assets, divided by the total number of common shares outstanding at the end of the performance period, which is December 31, 2023, and dividing that number by the same calculation at the beginning of the period, which is February 26, 2021. This calculation is annualized for the 34-month period between the beginning and the end of the performance period. The awards were scheduled to be earned in four installments, each with established threshold, target, and maximum goals.

  99. 2021-2023 PSUs

    | Performance Criteria | Weighting | Threshold (50% of Target) | Target | Maximum (150% of Target) | Actual Performance | Achievement as a % of Target | Vesting (weighted) | | TBVPS Growth (2021) | 25.0% | 1.0% | 3.0% | 4.5% | 1.6% | 66.0% | 16.5% | | TBVPS Growth (2022) | 25.0% | 4.0% | 6.0% | 8.0% | (20.6)% | 0% | 0% | | TBVPS Growth (2023) | 25.0% | 7.0% | 9.0% | 11.0% | 21.9% | 150.0% | 37.5% | | TBVPS CAGR (2021 - 2023) | 25.0% | 4.1% | 6.2% | 8.2% | (0.9)% | 0% | 0% | | Total | 100.0% | | | | | | 54.0% |

  100. 2021-2023 PSUs

    For each installment, if the performance threshold was missed, that portion of the award was cancelled while, if maximum performance was achieved, 150% of that portion of the award is earned. For any portion that is earned based on performance, the continuing NEOs will not be vested in such earned PSUs until the third anniversary of the date of grant (April 2024), subject to each NEO remaining employed by the Company through the payment date. Based on the performance above, Mr. Govrin is eligible to vest in 21,500 PSUs, subject to his continued employment through the third anniversary of the grant date in April 2024.

  101. 2021-2023 PSUs

    | X. | OTHER BENEFITS AND PERQUISITES |

  102. Perquisites

    | XI. | EMPLOYMENT AGREEMENTS AND SEPARATION AGREEMENTS WITH NEOs |

  103. Perquisites

    We have entered into employment agreements or offer letter agreements or similar agreements with each of the NEOs. We believe that it is beneficial to enter into compensation arrangements with our key executives that provide retentive value, subject executives to restrictive covenants and provide us with a competitive advantage in the recruiting process. The terms of these arrangements are more fully discussed below under “Narrative Disclosure to Summary Compensation Table and Grants of Plan-Based Awards for Fiscal Year 2023 Table—Employment Agreements.” In addition, during 2023, SiriusPoint International Insurance Corporation provided a separation letter to Mr. Liddell, which provided for certain severance benefits in lieu of his contractual notice period in connection with his termination of employment. The terms of this separation letter are more fully discussed below under “2023 Potential Payments Upon Termination or Change in Control.”

  104. Role of the Compensation Consultant

    Role of the Compensation Consultant Mercer, the Compensation Committee’s independent compensation consultant, reports directly to the Compensation Committee. Mercer’s advisory services primarily include:

  105. Role of the Compensation Consultant

    | ● | Providing expert input on industry trends, as well as executive compensation developments from a broader perspective; |

  106. Role of the Compensation Consultant

    | ● | Assessing the extent to which our pay levels and practices are competitively aligned with market practice; and |

  107. Role of the Compensation Consultant

    | ● | Facilitating objective, data-based compensation decisions in succession and annual pay planning processes. |

  108. Role of the Compensation Consultant

    The Committee retains sole authority to hire the compensation consultant, approve its compensation, determine the nature and scope of its services, evaluate its performance, and terminate and replace (or supplement) its engagement with an alternative consultant at any time. The Committee has assessed the independence of the compensation consultant pursuant to the listing standards of the NYSE and SEC rules and concluded that no conflict of interest exists that would prevent the compensation consultant from serving as an independent consultant to the Committee.

  109. Employment Agreements

    | (5) The exercise price for these stock options were inadvertently reported in the Outstanding Equity Awards at Fiscal Year-End 2022 table as $8.00 and $10.00. This table has been updated to reflect the exercise price set at the time of grant of $6.42 per share for these options. The options on these two lines became exercisable on the first date on which the closing stock price of SiriusPoint was at least $8 per share and $10 per share respectively. |

  110. Employment Agreements

    | (17) Mr. Liddell’s outstanding equity awards lapsed upon his termination of employment, effective as of July 12, 2023. |

  111. Outstanding Equity Awards

    Outstanding Equity Awards Restricted Share Awards As of December 31, 2023, Mr. Govrin held one restricted share award agreement under the 2013 Omnibus Incentive Plan. This restricted share award provided that in the event a termination of Mr. Govrin’s employment or services due to death or disability (as such term is defined in the 2013 Omnibus Incentive Plan) during the restricted period applicable to the award, the restricted shares will be deemed vested with respect to the number of restricted shares that would have vested had the executive’s service continued until the next vesting date immediately following such termination, with any remaining unvested restricted shares forfeited and cancelled. In addition, in the event of a “change in control” (as defined in the 2013 Omnibus Incentive Plan), prior to the end of the restricted period applicable to the restricted shares, if Mr. Govrin is terminated by the Company without “cause” (as defined in the 2013 Omnibus Incentive Plan) or resigns employment with the Company for “good reason” (as defined in the restricted share agreement) during the period that begins 90 days prior to the change in control and ends 24 months following the change in control, the restricted shares will be deemed fully vested as of the effective date of Mr. Govrin’s termination of service (or, in the case of termination prior to a change in control, the change in control). The 2013 Omnibus Incentive Plan further provides that (i) in the event of Mr. Govrin’s termination of employment without cause within three (3) months prior to the occurrence of a change in control, Mr. Govrin will be treated under the 2013 Omnibus Incentive Plan as if he had remained continuously employed until the change in control, and experienced a termination of employment or service immediately thereafter, and (ii) in the event of a change in control, the restriction period applicable to the restricted shares will lapse as of immediately prior to the change in control (but note that where a restricted share agreement provides for accelerated vesting upon a termination in connection with a change in control, such provision supersedes this single-trigger change in control provision set forth in the 2013 Omnibus Incentive Plan). Time-Based Restricted Share Unit Awards (RSUs) As of December 31, 2023, each of the continuing NEOs held one or more RSI awards under the 2013 Omnibus Incentive Plan. Under a number of these agreements, in the event of a “change in control” (as defined in the 2013 Omnibus Incentive Plan) prior to the end of the restricted period applicable to the RSUs, if the executive’s services are terminated by the applicable employing entity without “cause” (as defined in the applicable award agreement) or the executive resigns for “good reason” (as defined in the applicable award agreement) during the period that begins 90 days prior to the change in control and ends 24 months following the change in control, the RSUs will be deemed fully vested as of the effective date of the executive’s termination of service (or, in the event of a termination prior to a change in control, the change in control). In addition, in the event that the executive’s services are deemed terminated for death or “disability”(as defined in the 2013 Omnibus Incentive Plan) during the restricted period, then the RSUs will be deemed vested to the extent of the number of RSUs that would have vested had the participant’s service continued until the next vesting date immediately following such termination for death or disability. The remaining outstanding RSUs held by Messrs. Govrin and Egan under the 2013 Omnibus Incentive Plan generally provide that in the event of a “qualifying termination” (i.e., termination of employment as a result of death or “disability” as defined in the 2013 Omnibus Incentive Plan) or termination by the Company without cause or resignation by the executive for “good reason” (each as defined in the RSU agreement) at any time, their outstanding RSUs thereunder will be deemed fully vested effective as of the termination date. The additional outstanding RSU award held by Mr. Yendall provides that in the event of such a “qualifying termination” (which in the case of Mr. Yendall also includes a termination for “just cause”), all unvested RSUs will remain outstanding and be eligible to vest for twelve (12) months following the date of such termination of employment, or in the case of a qualifying termination during the period that begins 90 days prior to the change in control and ends 24 months following the change in control, the RSUs will be deemed fully vested as of the effective date of his termination of service (or, in the event of a termination prior to a change in control, the change in control). The 2013 Omnibus Incentive Plan further provides that in the event of the executive’s termination without cause within three (3) months prior to the occurrence of a change in control, such executive will be treated under the 2013 Omnibus Incentive Plan as if they had remained continuously employed until the change in control, and experienced a termination of employment immediately thereafter, and (ii) in the event of a change in control, the restriction period applicable to RSUs will lapse as of immediately prior to the change in control (but note that where an RSU agreement provides for accelerated vesting upon a termination in connection with a change in control, such provision supersedes this single-trigger change in control provision set forth in the 2013 Omnibus Incentive Plan). Performance-Based Restricted Share Unit Awards (PSUs) As of December 31, 2023, each of the then-serving NEOs held one or more outstanding PSU awards under the 2013 Omnibus Incentive Plan. Under Mr. Govrin’s 2021 PSU award, (i) in the event of a termination of the executive’s employment or services due to death or disability (as such term is defined in the 2013 Omnibus Incentive Plan) prior to the third anniversary of the grant date, the PSUs will be deemed vested to the extent of the number of PSUs that would have vested based on the achievement of the applicable performance goals at any time prior to the first anniversary following the date of such termination had such termination occurred, without any requirement of continued service, with any remaining unvested PSUs forfeited and cancelled, and (ii) in the event of a “change in control” (as defined in the 2013 Omnibus Incentive Plan) prior to the end of the restricted period applicable to the PSUs, if the executive is terminated by the Company without “cause” (as defined in the 2013 Omnibus Incentive Plan) or the executive resigns employment with the Company for “good reason” (as defined in the PSU agreements) during the period that begins 90 days prior to the change in control and ends twenty-four months following the change in control, the PSUs will vest on the effective date of the executive’s termination of service (or, in the event of a termination prior to a change in control, the change in control) at the greater of target levels or levels based on actual performance achieved through the end of the fiscal quarter ending immediately prior to the change in control, and any remaining unvested PSUs will be forfeited.

  112. Outstanding Equity Awards

    Under the 2023 PSU awards, (i) in the event of a termination of the executive’s employment or services due to death or disability prior to the third anniversary of the grant date, then a pro-rated portion of the PSUs will vest based upon the number of full months following the grant date during which the executive was employed (assuming target performance); provided, however, that if the performance period (which ends on December 31, 2025) has ended on or prior to the executive’s death or termination for disability, then the number of PSUs that will vest is instead determined based on actual performance during the performance period, and (ii) in the event of a “change in control” prior to the end of the restricted period applicable to the PSUs, if the executive is terminated by the Company without cause or the executive resigns employment with the Company for good reason, then the award will be treated as described above with respect to the 2021 PSUs. The 2013 Omnibus Incentive Plan further provides that in the event of the executive’s termination of employment or service without cause within three (3) months prior to the occurrence of a change in control, such executive will be treated under the 2013 Omnibus Incentive Plan as if they had remained continuously employed until the change in control, and experienced a termination of employment or service immediately thereafter. Option Awards As of December 31, 2023, Mr. Govrin held two unvested option awards granted under the 2013 Omnibus Incentive Plan. With respect to these option awards, upon a termination of employment, any unvested options are generally forfeited, provided that in the event of a “change in control” (as defined in the 2013 Omnibus Incentive Plan), prior to the end of the vesting period, if Mr. Govrin is terminated by his employer without “cause” (as defined in the 2013 Omnibus Incentive Plan) or resigns employment with his employer for “good reason” (as defined in the option agreements) during the period that begins 90 days prior to the change in control and ends 24 months following the change in control, the options will be deemed fully vested as of the effective date of such termination of service (or, in the event of a termination prior to a change in control, the change in control). The 2013 Omnibus Incentive Plan further provides that (i) in the event of the executive’s termination of employment or service due to death or “disability” (as defined in the 2013 Omnibus Incentive Plan), with respect to any awards thereunder which are subject solely to time-based restrictions, any such awards that would have become vested prior to the first anniversary of the executive’s termination date, had the executive continued to be employed by the Company through such date, will immediately become vested as of the termination date; and (ii) in the event of the executive’s termination of employment without cause within three (3) months prior to the occurrence of a change in control, such executive will be treated under the 2013 Omnibus Incentive Plan as if they had remained continuously employed or providing services until the change in control, and experienced a termination of employment or services immediately thereafter. The 2013 Omnibus Incentive Plan further provides that in the event of a change in control, all options will become immediately exercisable (provided that such awards may be cashed out or cancelled with appropriate notice, and provided further that where an option agreement provides for accelerated vesting upon a termination in connection with a change in control, such provision supersedes this single-trigger change in control provision set forth in the 2013 Omnibus Incentive Plan). Other than as described above, unvested equity incentive awards held by each of the NEOs will automatically be cancelled and forfeited upon the NEO’s termination of employment or service.

  113. Potential Payments Upon a Qualifying Termination of Employment Absent a Change in Control(1)

    Potential Payments Upon a Qualifying Termination of Employment Absent a Change in Control(1)

  114. Potential Payments Upon a Qualifying Termination of Employment Absent a Change in Control(1)

    | Name | Cash Severance Payment | Value of Acceleration/ | Continuing Welfare | Aggregate | | | ($)(2) | Lapse of Restrictions on | Insurance Benefit | Payments ($) | | | | Equity Awards ($)(3) | ($)(4) | | | Scott Egan | 4,191,000 | 2,352,944 | 92,390 | 6,636,334 | | Stephen Yendall | 1,031,864 | 529,784 | 17,647 | 1,579,295 | | David E. Govrin | 1,722,500 | 7,531,279 | 24,454 | 9,278,233 | | Rob Gibbs | 1,265,391 | 0 | 6,203 | 1,271,594 |

  115. Potential Payments Upon a Qualifying Termination of Employment Absent a Change in Control(1)

    | (1) “Qualifying termination” means, in the case of the continuing NEOs, a resignation of employment by the NEO for good reason (excluding, in the case of Messrs. Egan and Gibbs, termination as a result of death or disability, which is separately addressed in the “Potential Payments Upon Death or Disability” table below) or a termination of employment by the employer without cause (or in the case of benefits under the Yendall Agreement, without cause and without just cause). |

  116. Potential Payments Upon a Qualifying Termination of Employment Absent a Change in Control(1)

    | (2) Amounts reported in this column represent cash severance payments to each of the continuing NEOs in the event of a qualifying termination outside of the change in control period for the 2013 Omnibus Incentive Plan (in the case of awards under the 2013 Omnibus Incentive Plan, beginning ninety (90) days prior to and ending twenty-four (24) months following a change in control (as defined in the 2013 Omnibus Incentive Plan)). Mr. Yendall’s cash severance payment has been calculated disregarding the value of any potential statutory severance entitlements. |

  117. Potential Payments Upon a Qualifying Termination of Employment Absent a Change in Control(1)

    | (3) Reflects the value of the accelerated vesting or lapse of continuing service requirements with respect to certain outstanding unvested equity awards in connection with a qualifying termination outside of the change in control period for the 2013 Omnibus Incentive Plan as described above. The value of such accelerated vesting or lapse of continuing service restrictions with respect to the equity awards reported in this table is based upon our closing share price of $11.60 on December 29, 2023. For purposes of calculating the value of accelerated vesting of Mr. Govrin’s PSU awards pursuant to Mr. Govrin’s employment agreement, the Company has assumed that such PSU awards would become vested at target levels. |

  118. Potential Payments Upon a Qualifying Termination of Employment Absent a Change in Control(1)

    | (4) Reflects the cost to us of the continued provision of medical and life insurance benefits for eighteen (18) months following Mr. Egan’s termination date and twelve (12) months following Mr. Gibbs’s termination date, as well as continuation of employer contributions or premiums with respect to coverage for all benefits under any benefit plan for the twelve (12)-month period after the termination date for Mr. Yendall and subsidized COBRA continuation coverage for twelve (12) months at active employee rates for Mr. Govrin. |

  119. Potential Payments Upon Death or Disability

    Potential Payments Upon Death or Disability

  120. Potential Payments Upon Death or Disability

    | Name | Cash Severance | Value of Acceleration/ | Continuing Welfare | Aggregate | | | Payment($)(1) | Lapse of Restrictions | Insurance Benefit ($)(3) | Payments ($) | | | | on Equity Awards ($)(2) | | | | Scott Egan | 4,191,000 | 3,881,971 | 92,390 | 8,165,361 | | Stephen Yendall | 0 | 787,370 | 0 | 787,370 | | David E. Govrin | 0 | 5,076,709 | 0 | 5,076,709 | | Rob Gibbs | 1,265,391 | 303,382 | 6,203 | 1,574,976 |

  121. Potential Payments Upon Death or Disability

    | (1) Amounts reported in this column represent cash severance amounts payable in connection with termination of employment as a result of death or permanent disability, in accordance with the terms of the applicable employment agreement. |

  122. Potential Payments Upon Death or Disability

    | (2) Reflects the value of the accelerated vesting or lapse of continuing service requirements with respect to certain outstanding unvested RSU awards, restricted share awards and options in connection with a termination of employment as a result of death or disability as described above. The value of such accelerated vesting or lapse of continuing service restrictions with respect to the equity awards reported in this table is based upon our closing share price of $11.60 on December 30, 2023. |

  123. Potential Payments Upon Death or Disability

    | (3) Reflects the cost to us of the continued provision of medical and life insurance benefits for eighteen (18) months following Mr. Egan’s termination date and twelve (12) months following Mr. Gibbs’s termination date (to the extent applicable). |

  124. Potential Payments Upon a Qualifying Termination of Employment in Connection with a Change in Control(1)

    Potential Payments Upon a Qualifying Termination of Employment in Connection with a Change in Control(1)

  125. Potential Payments Upon a Qualifying Termination of Employment in Connection with a Change in Control(1)

    | Name | Cash Severance | Value of Acceleration/ | Continuing Welfare | Aggregate | | | Payment ($)(2) | Lapse of Restrictions | Insurance Benefit | Payments ($) | | | | on Equity Awards ($)(3) | ($)(4) | | | Scott Egan | 4,191,000 | 8,354,749 | 92,390 | 12,638,139 | | Stephen Yendall | 1,031,864 | 2,227,246 | 17,647 | 3,276,757 | | David E. Govrin | 1,722,500 | 7,846,079 | 24,454 | 9,593,033 | | Rob Gibbs | 1,265,391 | 1,190,844 | 6,203 | 2,462,438 |

  126. Potential Payments Upon a Qualifying Termination of Employment in Connection with a Change in Control(1)

    | (1) “Qualifying termination” means, in the case of the continuing NEOs, a resignation of employment by the NEO for good reason (including, in the case of Messrs. Egan and Gibbs, a termination as a result of death or permanent disability) or a termination of employment by the employer without cause (or in the case of benefits under the Yendall Agreement, without cause and without just cause), during the relevant change in control period (in the case of awards under the 2013 Omnibus Incentive Plan, beginning ninety (90) days prior to and ending twenty-four (24) months following a change in control (as defined in the Omnibus Incentive Plan). |

  127. Potential Payments Upon a Qualifying Termination of Employment in Connection with a Change in Control(1)

    | (2) Amounts reported in this column represent cash severance payments to each of the continuing NEOs in the event of a qualifying termination during the applicable change in control period. |

  128. Potential Payments Upon a Qualifying Termination of Employment in Connection with a Change in Control(1)

    | (3) Reflects the value of the accelerated vesting of certain outstanding, unvested equity awards in connection with a qualifying termination in connection with a change in control as described above. For all NEOs, these calculations assume that the NEO experiences a qualifying termination of employment immediately following a change in control on December 29, 2023. The value of the accelerated vesting of equity awards reported in this table is based upon our closing share price of $11.60 on December 29, 2023. With respect to the PSU awards held by Mr. Govrin, the value reflected in this column assumes that such awards would undergo accelerated vesting at target levels. |

  129. Potential Payments Upon a Qualifying Termination of Employment in Connection with a Change in Control(1)

    | (4) Reflects the cost to us of the continued provision of medical and life insurance benefits for eighteen (18) months following Mr. Egan’s termination date, and twelve (12) months following Mr. Gibbs’s termination date, as well as the continuation of employer contributions or premiums with respect to coverage for all benefits under any benefit plan for the twelve (12) month period after the termination date for Mr. Yendall and subsidized COBRA continuation coverage for twelve (12) months at active employee rates for Mr. Govrin. |

  130. Potential Payments Upon a Qualifying Termination of Employment in Connection with a Change in Control(1)

    In addition to the amounts set forth in the tables above, in the event of a Change in Control (absent a termination) on December 31, 2023, pursuant to the terms of Mr. Govrin’s employment agreement, Mr. Govrin would have been entitled to accelerated vesting of all of his then-outstanding and unvested stock option awards, with a fair market value of approximately $394,970 as of December 31, 2023. For purposes of these tables, with respect to treatment of outstanding equity awards in connection with a change in control, we have assumed that all such awards have been effectively substituted, assumed or continued by the surviving or acquiring corporation and that the awards are subject to the double-trigger vesting provisions set forth in the underlying award agreements.

  131. CEO PAY RATIO DISCLOSURE

    CEO PAY RATIO DISCLOSURE We believe our executive compensation program must be consistent and internally equitable to motivate our employees to perform in ways that enhance shareholder value. We are committed to internal pay equity, and the Compensation Committee monitors the relationship between the pay of our executive officers and the pay of our non-executive employees. In 2023, we determined to identify our median employee, using base salary for fiscal year 2023 of each of our employees (excluding the CEO) employed as of December 1, 2023. We determined the compensation of our median employee by:

  132. CEO PAY RATIO DISCLOSURE

    | (i) determining the base salary for each of our employees (excluding our CEO); |

  133. CEO PAY RATIO DISCLOSURE

    | (ii) ranking the base salary of all employees except for our CEO from lowest to highest (a list of 1,004 employees); and |

  134. CEO PAY RATIO DISCLOSURE

    | (iii) | selecting the median employee as described above. |

  135. CEO PAY RATIO DISCLOSURE

    All active employees working on a full-time, part-time, or interim basis were included. To facilitate comparison of all employees in U.S. dollars, compensation paid in foreign currencies was converted to U.S. dollars. We applied a local currency to U.S. dollar exchange rate on December 29, 2023. We annualized the compensation for employees who began employment after the start of the fiscal year or who were on an unpaid leave of absence during the fiscal year. Upon identifying the median employee, total compensation was calculated for this individual using the same methodology we use for our NEOs as set forth in the 2023 Summary Compensation Table. For fiscal year 2023, our last completed fiscal year:

  136. CEO PAY RATIO DISCLOSURE

    | | 2023 ANNUAL TOTAL COMPENSATION | | | EMPLOYEE | ($) | ESTIMATED PAY RATIO | | Scott Egan, our CEO | 10,282,470 | 93:1 | | Median employee, other than our CEO | 110,482 | |

  137. CEO PAY RATIO DISCLOSURE

    Based on this information, for 2023 the reasonable estimated ratio of the annual total compensation of our CEO, to the median of the annual total compensation of all employees, calculated in a manner consistent with Item 402(u) of Regulation S-K, was 93:1.

  138. PAY VERSUS PERFORMANCE

    PAY VERSUS PERFORMANCE The following table sets forth information concerning: (1) the compensation of our Chief Executive Officer (Mr. Egan), our former Chief Executive Officer (Mr. Malloy), our former Chief Executive Officer and Director (Mr. Sankaran) (the Company’s Principal Executive Officers, or “PEOs”), and the average compensation for our other Named Executive Officers, both as reported in the Summary Compensation Table and with certain adjustments to reflect the “compensation actually paid” to such individuals, as defined under SEC rules, for each of the fiscal years ended December 31, 2020, 2021, 2022 and 2023 and (2) and our cumulative total shareholder return (“TSR”), the cumulative TSR of our comparator group (“Comparator Group TSR”), Net Income and Core Combined Ratio over such years in accordance with SEC rules performance for each such fiscal year:

  139. PAY VERSUS PERFORMANCE

    | (a) | (b) | (b) | (b) | (c) | (c) | (c) | (d) | (e) | (f) | (g) | (h) | (i) | | Year(1) | SCT Total for Mr. Egan ($)(2) | SCT Total for Mr. Malloy ($)(2) | SCT Total for Mr. Sankaran ($)(2) | Comp. Actually Paid to Mr. Egan ($)(2)(3) | Comp. Actually Paid to Mr. Malloy ($)(2)(3) | Comp. Actually Paid to Mr. Sankaran ($)(2)(3) | Average SCT Total for Non-PEO NEOs ($)(1)(2) | Average Comp. Actually Paid to Non-PEO NEOs ($)(2)(3) | Value of Initial Fixed $100 Investment Based on: | | Net Income ($MMs) | Core Combined Ratio(5) | | | | | | | | | | | Total Shareholder Return ($) | Comparator Group Total Shareholder Return ($)(4) | | | | 2023 | 10,282,470 | — | — | 16,426,982 | — | — | 2,386,159 | 3,990,654 | 110.27 | 164.4 | 355 | 89.1% | | 2022 | 5,818,004 | 5,559,656 | 14,025,109 | 6,972,607 | 2,413,083 | 524,638 | 2,764,751 | 1,444,040 | 56.08 | 144.76 | -387 | 101.5% | | 2021 | — | 4,168,265 | 12,374,251 | — | 3,786,356 | 8,977,855 | 2,794,042 | 2,459,819 | 77.28 | 125.88 | 58 | 99.7% | | 2020 | — | 3,254,510 | — | — | 1,697,106 | — | 1,758,356 | 1,527,848 | 90.49 | 103.11 | 144 | 110.3% |

  140. PAY VERSUS PERFORMANCE

    | (1) The following individuals are our NEOs for each fiscal year: |

  141. PAY VERSUS PERFORMANCE

    | YEAR | PEOs | Non-CEO NEOs | | 2023 | Scott Egan | Stephen Yendall, David E Govrin, Rob Gibbs, and Stuart Liddell | | 2022 | Scott Egan, Daniel Malloy, and Siddhartha Sankaran | Monica Cramér Manheim, Stuart Liddell, Prashanth Gangu, David E. Govrin, David W. Junius, Stephen Yendall, and Vievette Henry | | 2021 | Daniel Malloy, and Siddhartha Sankaran | Monica Cramér Manheim, Prashanth Gangu, David E. Govrin, David W. Junius, and Christopher Coleman | | 2020 | Daniel Malloy | David E. Govrin, David W. Junius, Nicholas J.D. Campbell and Christopher Coleman |

  142. PAY VERSUS PERFORMANCE

    | (2) The amounts reported for 2022 and 2021 have been updated from the amounts reported in the 2023 proxy statement to reflect the inadvertent exclusion of certain equity awards from Summary Compensation Table values and/or the compensation actually paid calculation. |

  143. PAY VERSUS PERFORMANCE

    | (3) Compensation actually paid to our NEOs represents the “Total” compensation reported in the Summary Compensation Table for the applicable fiscal year, adjusted as set forth below. Amounts set forth in this table were computed in accordance with the methodology used for financial reporting purposes and, for performance-based equity awards, calculated based on the probable outcome of such performance-based vesting conditions as of the last day of the fiscal year. |

  144. PAY VERSUS PERFORMANCE

    | | 2020 | | 2021 | | | 2022 | | | | 2023 | | | Adjustments | Mr. Malloy | Average non-PEO NEOs | Mr. Malloy | Mr. Sankaran | Average non-PEO NEOs | Mr. Egan | Mr. Malloy | Mr. Sankaran | Average non-PEO NEOs | Mr. Egan | Average non-PEO NEOs | | Deduction for Amounts Reported under the “Stock Awards” and “Option Awards” Columns in the SCT for Applicable FY | (1,487,518) | (925,321) | (2,373,160) | (10,857,790) | (1,394,269) | (5,002,002) | (3,151,143) | (9,588,400) | (1,414,755) | (4,889,402) | (1,121,703) | | Increase based on ASC 718 Fair Value of Awards Granted during Applicable FY that Remain Unvested as of Applicable FY End, determined as of Applicable FY End | 1,081,235 | 976,441 | 2,685,238 | 7,964,328 | 1,638,868 | 5,493,814 | — | 800,845 | 928,396 | 6,001,805 | 1,283,784 | | Increase based on ASC 718 Fair Value of Awards Granted during Applicable FY that Vested during Applicable FY, determined as of Vesting Date | — | — | — | — | 109,851 | 662,791 | 808,200 | — | 6,286 | — | — | | Increased/deduction for Awards Granted during Prior FY that were Outstanding and Unvested as of Applicable FY End, determined based on change in ASC 718 Fair Value from Prior FY End to Applicable FY End | (954,558) | (221,696) | (50,078) | (506,683) | (53,662) | — | (636,072) | (1,755,184) | (157,391) | 1,156,188 | 774,538 | | Increased/deduction for Awards Granted during Prior FY that Vested During Applicable FY, determined based on change in ASC 718 Fair Value from Prior FY End to Applicable FY Vesting Date | (91,513) | (28,398) | 57,535 | 3,749 | 35,337 | — | (117,940) | (183,856) | (94,094) | 3,875,921 | 753,659 | | Deduction of ASC 718 Fair Value of Awards Granted during Prior FY that were Forfeited during Applicable FY, determined as of Prior FY End | (105,050) | (31,535) | (701,444) | — | (670,349) | — | (49,617) | (2,773,876) | (593,153) | — | (85,784) | | Increase based on Dividends or Other Earnings Paid during Applicable FY prior to Vesting Date | — | — | — | — | — | — | — | — | — | — | — | | TOTAL ADJUSTMENTS | (1,557,404) | (230,508) | (381,909) | (3,396,396) | (334,223) | 1,154,604 | (3,146,573) | (13,500,471) | (1,324,711) | 6,144,512 | 1,604,494 |

  145. PAY VERSUS PERFORMANCE

    | (4) TSR is cumulative for the measurement periods beginning on December 31, 2019 and ending on December 31 of each of 2023, 2022, 2021 and 2020, respectively, calculated in accordance with Item 201(e) of Regulation S-K. The Dow Jones U.S. Property & Casualty Index is the same index we use in our performance graph in the Company’s Annual Reports on Form 10-K for the year ended December 31, 2023. |

  146. PAY VERSUS PERFORMANCE

    | (5) “Core Combined Ratio” is a non-GAAP measure which is calculated by dividing the sum of Core loss and loss adjustment expenses incurred, net, acquisition costs, net and other underwriting expenses by Core net premiums earned. This ratio, which is one of the |

  147. PAY VERSUS PERFORMANCE

    selected performance metrics under the Company’s annual cash incentive program for 2023, is a key indicator of our underwriting profitability, and the Compensation Committee has determined that this measure represents the most important financial performance measure used by the Company to link compensation actually paid to the Company’s NEOs to Company performance. Appendix A to this Proxy Statement includes a reconciliation of such non-GAAP financial measures to the most directly comparable financial measure prepared in accordance with GAAP.

  148. Narrative Disclosure to Pay Versus Performance Table

    Narrative Disclosure to Pay Versus Performance Table Relationship between Financial Performance Measures The line graphs below compare (i) the compensation actually paid to our PEO(s) and the average of the compensation actually paid to our remaining NEOs, with (ii) our cumulative TSR, (iii) Peer Group TSR, (iv) our Net Income, and (v) our Core Combined Ratio, in each case, for the fiscal years ended December 31, 2020, 2021, 2022 and 2023. TSR amounts reported in the graph assume an initial fixed investment of $100, and that all dividends, if any, were reinvested. Pay Versus Performance Tabular List The following performance measures represent the most important financial and strategic performance measures used by us to link compensation actually paid to our NEOs to performance for the fiscal year ended December 31, 2023:

  149. Narrative Disclosure to Pay Versus Performance Table

    | ● | Core Combined Ratio; |

  150. Narrative Disclosure to Pay Versus Performance Table

    | ● | Tangible NBVPS compound annualized growth rate; and |

  151. Narrative Disclosure to Pay Versus Performance Table

    | ● | Cost base reduction |

  152. Narrative Disclosure to Pay Versus Performance Table

    | AUDIT MATTERS |

  153. Narrative Disclosure to Pay Versus Performance Table

    | PROPOSAL 3 | APPOINTMENT OF INDEPENDENT AUDITOR & TO DETERMINE THE INDEPENDENT AUDITOR’S REMUNERATION | | TO APPOINT PRICEWATERHOUSECOOPERS LLP, AN INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM, AS OUR INDEPENDENT AUDITOR TO SERVE UNTIL THE ANNUAL GENERAL MEETING TO BE HELD IN 2025, AND TO AUTHORIZE OUR BOARD, ACTING BY THE AUDIT COMMITTEE, TO DETERMINE THE INDEPENDENT AUDITOR’S REMUNERATION | |

  154. Narrative Disclosure to Pay Versus Performance Table

    The Board proposes and recommends that the shareholders appoint the firm of PricewaterhouseCoopers LLP (“PwC”), an independent registered certified public accounting firm, as our independent auditor to serve until the annual general meeting to be held in 2025. PwC has served as our independent auditor since February 26, 2021, the date of the consummation of the Merger. A representative of PwC will attend the Annual General Meeting virtually and will have an opportunity to make a statement, if he or she desires to do so, and to respond to appropriate questions. Shareholders at the Annual General Meeting will also be asked to vote to authorize our Board, acting by the Audit Committee, to determine the independent auditor’s remuneration. If a quorum is present at the Annual General Meeting, the appointment of PwC at the Annual General Meeting will be decided by a majority of votes cast. For further information, see the answers to the questions “What is the quorum requirement for the Annual General Meeting?” and “What is the voting requirement to approve each of the proposals?”

  155. Narrative Disclosure to Pay Versus Performance Table

    | | THE AUDIT COMMITTEE AND THE BOARD UNANIMOUSLY RECOMMEND THAT YOU VOTE FOR THE APPOINTMENT OF PRICEWATERHOUSECOOPERS LLP, AN INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM, AS OUR INDEPENDENT AUDITOR TO SERVE UNTIL THE ANNUAL GENERAL MEETING TO BE HELD IN 2025, AND TO AUTHORIZE OUR BOARD, ACTING BY THE AUDIT COMMITTEE, TO DETERMINE THE INDEPENDENT AUDITOR’S REMUNERATION. |