DEF 14A of Baldwin Insurance Group, Inc., Apr 22, 2026

DEF 14A of Baldwin Insurance Group, Inc.

Filed Apr 22, 2026 · FY20250001781755-26-000027

Open on EDGAR
  1. Table of Contents

    | Compensation Tables | | 51 | | Summary Compensation Table | | 51 | | Grants of Plan Based Awards for Fiscal Year 2025 | | 52 | | Outstanding Equity Awards at 2025 Fiscal Year-End | | 53 | | Options Exercised and Stock Vested for Fiscal Year 2025 | | 54 | | Equity Compensation Plans | | 55 | | Employment Agreements | | 56 | | Potential Payments Upon Termination or Change in Control | | 57 | | Pay Versus Performance | | 60 | | Pay Versus Performance Table | | 60 | | Pay Versus Performance Graphs | | 62 | | Financial Performance Measures | | 63 | | CEO Pay Ratio | | 64 | | Security Ownership of Certain Beneficial Owners and Management | | 65 | | Beneficial Ownership of Directors and Executive Officers | | 65 | | Beneficial Ownership of More Than 5% Owners | | 66 | | Proposal No. 3: Ratification for the Selection of PricewaterhouseCoopers LLP as our Independent Registered Public Accounting Firm | | 68 | | Audit Committee Matters | | 69 | | Audit Committee Report | | 69 | | Information About Voting and the Meeting | | 70 | | Appendix: Non-GAAP Financial Measures | A-1 | |

  2. Class I Director Nominees up for Election at the 2026 Annual Meeting

    Class I Director Nominees up for Election at the 2026 Annual Meeting

  3. Class I Director Nominees up for Election at the 2026 Annual Meeting

    | | | | | Committees | | | | | | Name | Age | Director Since | Independence | AC | CC | EC | NCGC | TCRC | | Lowry Baldwin | 67 | September 2019 | Non-Independent | | | | | | | Sathish Muthukrishnan | 52 | June 2023 | Independent | | | | | • | | Sunita Parasuraman | 53 | January 2022 | Independent | | | | | | | Ellyn Shook | 62 | January 2022 | Independent | | • | | | |

  4. Class I Director Nominees up for Election at the 2026 Annual Meeting

    • = Committee Chairperson • = Committee Member AC = Audit Committee CC = Compensation Committee EC = Executive Committee NCGC = Nominating & Corporate Governance Committee TCRC = Technology & Cyber Risk Committee

  5. Proposal No. 1: Election of Directors

    Proposal No. 1: Election of Directors Our Board of Directors currently consists of 11 directors: Lowry Baldwin, Trevor Baldwin, Jay Cohen, Joseph Kadow, Barbara Matas, Sathish Muthukrishnan, Sunita Parasuraman, Ellyn Shook, Paul Sparks, Chris Sullivan and Myron Williams. The Class I directors whose terms expire at the Annual Meeting are Lowry Baldwin, Sathish Muthukrishnan, Sunita Parasuraman and Ellyn Shook. At the Annual Meeting, the Board is recommending that the shareholders elect Lowry Baldwin, Sathish Muthukrishnan, Sunita Parasuraman and Ellyn Shook to serve as Class I directors for a term ending at the annual meeting of shareholders to be held in 2029. Shares represented by executed proxies will be voted, if authority to do so is not withheld, for the election of the four nominees named below. In the event that any nominee should be unavailable for election as a result of an unexpected occurrence, those shares will be voted for the election of those substitute nominee(s) as the Board of Directors may propose or the Board may reduce its size. Each person nominated for election has agreed to serve if elected, and management has no reason to believe that any nominee will be unable to serve. Directors are elected by a plurality of the votes of the shares cast at the meeting (excluding “Withheld” and broker non-votes, which will not affect the outcome of the vote). This means that the nominees receiving the highest number of affirmative (“FOR”) votes (among votes properly cast in-person or by proxy) will be elected as directors. The following table sets forth information with respect to each nominee’s position and office held with the Company and each nominee’s age as of the date of this Proxy:

  6. Proposal No. 1: Election of Directors

    | Name | Age | Position | Director Since | | Lowry Baldwin | 67 | Director | September 2019 | | Sathish Muthukrishnan | 52 | Director | June 2023 | | Sunita Parasuraman | 53 | Director | January 2022 | | Ellyn Shook | 62 | Director | January 2022 |

  7. Proposal No. 1: Election of Directors

    Set forth in "Director Nominees" below is biographical information for each nominee, including certain information regarding our nominees’ individual experience, qualifications, attributes and skills that led the Board of Directors to conclude that they should serve as directors and that they should be elected at the Annual Meeting.

  8. Proposal No. 1: Election of Directors

    | The Board of Directors unanimously recommends that you vote FOR the election of each nominee listed above to serve as director until the 2029 annual meeting or until his or her successor is duly elected and qualified. | |

  9. Proposal No. 1: Election of Directors

    | | 2026 Proxy Statement | 5 |

  10. Proposal No. 1: Election of Directors

    | PROPOSAL NO. 1 | TABLE OF CONTENTS |

  11. Director Nominees

    Director Nominees

  12. Director Nominees

    | | | | | | | EXPERIENCE | | | | •Board Chair since formation of The Baldwin Group in 2019 •In 2011, co-founded The Baldwin Group with his partners, Trevor Baldwin, Elizabeth Krystyn and Laura Sherman, to serve as a holding company for further investment into the insurance brokerage space •In 2006, formed what is today our middle market business with his partners •In 1997, co-founded Advantec Solutions, Inc., a national professional employer organization serving small and mid-size businesses by providing outsourced payroll, human resources, employee benefits and benefits administration, and workers’ compensation •In 1991, co-founded Davis Baldwin Insurance and Risk Management •In 1983, joined Baldwin & Sons •In 1981, began insurance career at Aetna Property & Casualty | | | Lowry Baldwin | | | | Board Chair | | | | Age: 67 | | | | Director Since: September 2019 (Non-Independent) | | | | | EDUCATION | | | | •BS in Psychology, Wake Forest University | | | Committees: •Executive | | | | | OTHER PROFESSIONAL AND CHARITABLE AFFILIATIONS | | | Father of Trevor Baldwin | •Board Member, University of Tampa |

  13. Director Nominees

    | | | | | | | EXPERIENCE | | | | •From 2020 to 2026, served as Chief Information, Data and Digital Officer at Ally Financial, Inc. •From 2017 to 2020, served as Chief Digital & Information Officer and Chief Technology Officer at Honeywell Aerospace •From 2007 to 2017, served as CIO - Enterprise Digital at American Express •From 1999 to 2006, served as Enterprise Software Architect at United Airlines | | | Sathish Muthukrishnan | | | | | EDUCATION | | | Age: 52 | •Engineering (Computer Science), University of Madras | | | Director Since: June 2023 (Independent) | OTHER PROFESSIONAL AND CHARITABLE AFFILIATIONS | | | | •Board Member, Road to Hire •Board Member, MMA Chief Digital Officers Board •Advisory Board Member, WIT International | | | Committees: •Technology and Cyber Risk (Chair) | |

  14. Director Nominees

    | 6 | 2026 Proxy Statement | |

  15. Director Nominees

    | TABLE OF CONTENTS | PROPOSAL NO. 1 |

  16. Director Nominees

    | | | | | | | EXPERIENCE | | | | •From 2020 to 2023, served as Head of Investments, New Product Experimentation at Meta (previously Facebook) •From 2018 to 2020, served as Head of Treasury for Facebook's blockchain initiative •From 2011 to 2018, served as Global Head of Treasury for Facebook | | | Sunita Parasuraman | | | | | EDUCATION | | | | •M.B.A. in Finance, University of California, Berkeley •Master in Engineering, University of Pennsylvania •BS in Engineering, Indian Institute of Technology, Bombay | | | Age: 53 | | | | Director Since: January 2022 (Independent) | | | | | OTHER PUBLIC COMPANY BOARDS | | | Committees: •Audit •Technology and Cyber Risk | •Board Member and Audit Committee Chair, IREN Limited (2023 to present) •Board Member and Audit Committee Chair, BitGo, Inc. (2026 to present) | | | | OTHER PROFESSIONAL AND CHARITABLE AFFILIATIONS | | | | •Board Member, Chair of the Nomination and Governance Committee and Member of the Finance Committee of the IIT Bombay Heritage Foundation •Board Member, Sri Ramana Maharshi Heritage |

  17. Director Nominees

    | | | | | | | EXPERIENCE | | | | •From September 2024 through September 2025, served as Accenture Luminary, Senior Client Advisor •From March 2014 to 2024, served as Chief Leadership and Human Resources Officer for Accenture •From 2004 to 2014, served in Chief Human Resources and Global Human Resources roles with Accenture | | | Ellyn Shook | | | | | EDUCATION | | | | •BS in Restaurant, Hotel, and Institutional Management, Purdue University | | | Age: 62 | | | | Director Since: January 2022 (Independent) | OTHER PUBLIC COMPANY BOARDS | | | | •Board Member and Chair of the Compensation and Talent Committee, Sandisk Corporation (2025 to present) •Observer, Schneider Electric SE | | | Committees: •Compensation (Chair) •Nominating and Corporate Governance | | | | | OTHER PROFESSIONAL AND CHARITABLE AFFILIATIONS | | | | •Executive Committee Member, Professional Roundtable of CHROs •Board Member, National Academy of HR |

  18. Director Nominees

    | | 2026 Proxy Statement | 7 |

  19. Director Nominees

    | PROPOSAL NO. 1 | TABLE OF CONTENTS |

  20. Other Current Directors

    Other Current Directors

  21. Other Current Directors

    | | | | | | | EXPERIENCE | | | | •Since May 2019, serves as Chief Executive Officer of The Baldwin Group •In 2011, co-founded The Baldwin Group with his partners, Lowry Baldwin, Elizabeth Krystyn and Laura Sherman, to serve as a holding company for further investment into the insurance brokerage space, going on to serve as President and Chief Operating Officer •In 2009, joined what is today our middle market business as a Commercial Risk Advisor, working primarily with healthcare and private equity clients, and, over time, led the firm’s Commercial Risk Management Group as Managing Director •Prior to joining The Baldwin Group, worked at HealthEdge Investment Partners, LLC, a private equity firm | | | Trevor Baldwin | | | | Chief Executive Officer | | | | | EDUCATION | | | Age: 40 | | | | | •BA in Risk Management & Insurance, Florida State University | | | Director Since: September 2019 (Non-Independent) | | | | | OTHER PROFESSIONAL AND CHARITABLE AFFILIATIONS | | | | •Manager, Emerald Bay Risk Solutions, LLC •Board Member, The HopeWill Foundation | | | Committees: •Executive | | | | Son of Lowry Baldwin | |

  22. Other Current Directors

    | | | | | | | EXPERIENCE | | | | •From 1995 to 2020, served as Managing Director of Equity Research, BofA Securities Inc., where he covered property and casualty insurance companies and insurance brokers •From 1990 to 1995, served as an Analyst, Equity Research, Salomon Brothers •From 1987 to 1989, served as a Senior Representative, Bond Department, Aetna Casualty & Surety | | | Jay Cohen | | | | | EDUCATION | | | | •MBA in Finance, Columbia University •BA in Managerial Economics, Union College | | | Age: 60 | | | | Director Since: June 2021 (Independent) | | | | | OTHER PROFESSIONAL AND CHARITABLE AFFILIATIONS | | | | •Board Member, Stamford Museum and Nature Center •Previously served as Board Member, Association of Insurance and Financial Analysts | | | Committees: •Audit •Compensation | |

  23. Other Current Directors

    | 8 | 2026 Proxy Statement | |

  24. Other Current Directors

    | TABLE OF CONTENTS | PROPOSAL NO. 1 |

  25. Other Current Directors

    | | | | | | | EXPERIENCE | | | | •Since February 2026, serves as interim General Counsel at Cava Group, Inc. •From 2005 to July 2019, served as Executive Vice President and Chief Legal Officer, Bloomin’ Brands, Inc., which owns Outback Steakhouse, Carrabba’s Italian Grill, Bonefish Grill and Fleming’s Prime Steakhouse and Wine Bar | | | | EDUCATION | | | Joseph Kadow | •JD, Dickinson School of Law at Pennsylvania State University •BS in Accounting, University of Scranton | | | Age: 69 | OTHER PUBLIC COMPANY BOARDS | | | | •Past Board Member, Audit Committee Member, and Chair of the Special Committee of Habit Restaurants, Inc. until March 2020, when Habit Restaurants, Inc. was acquired by Yum! Brands, Inc. (September 2015 to March 2020) | | | Director Since: February 2020 (Independent) | | | | Committees: •Nominating and Corporate Governance (Chair) •Audit | | | | | OTHER PROFESSIONAL AND CHARITABLE AFFILIATIONS | | | | •Past Chairman of the Board, National Restaurant Association •Board Member, Funding Florida Legal Aid (formerly Florida Bar Foundation) |

  26. Other Current Directors

    | | | | | | | EXPERIENCE | | | | •From 1999 to 2016, held various leadership positions with Citigroup, such as Managing Director, Head and Co-Head and Chairman of Leveraged Finance Capital Markets •From 1985 to 1999, served as a banker in the high-yield capital markets groups of Citicorp and Salomon Brothers | | | | EDUCATION | | | Barbara Matas | | | | | •MBA in Finance, University of Michigan •BS in Accounting and Quantitative Analysis, New York University | | | Age: 66 | | | | | OTHER PUBLIC COMPANY BOARDS | | | Director Since: February 2020 (Independent) | | | | | •Board Member, Nominating and Corporate Governance Committee Member, and Chair of Audit Committee, MidCap Financial Investment Corporation (formerly Apollo Investment Corporation) (2017 to present) •Previously Board Member, Chair of Capital Allocation Committee, Audit Committee Member, and former Chair of Audit Committee, Sleep Number Corporation (2016 to 2025) | | | Committees: •Audit (Chair) •Technology and Cyber Risk | | | | | OTHER PROFESSIONAL AND CHARITABLE AFFILIATIONS | | | | •Board Member and Chair of the Investment Committee, DOROT •Trustee and Chair of Audit Committee, Middle Market Apollo Institutional Private Lending BDC |

  27. Other Current Directors

    | | 2026 Proxy Statement | 9 |

  28. Other Current Directors

    | PROPOSAL NO. 1 | TABLE OF CONTENTS |

  29. Other Current Directors

    | | | | | | | EXPERIENCE | | | | •Since January 2026, serves as Strategic Advisor and Director of The Baldwin Group •From its founding in 2019 to 2026, served as Executive Chairman of CAC Group, Inc. •From 1998 to 2019, Executive at McGriff, Seibels & Williams, Inc., an insurance brokerage firm, and was the founder of McGriff's financial services practice prior to McGriff's sale to BB&T Insurance Services (now Truist) •Prior to his role at McGriff, served as an Executive Team Leader at Aon Plc and as Underwriting Lead at Chubb | | | Paul Sparks | | | | Age: 64 | | | | | EDUCATION | | | Director Since: January 2026 (Non-Independent) | •BA in Finance, Georgia State University | | | | OTHER PROFESSIONAL AND CHARITABLE AFFILIATIONS | | | | •Board Member, Georgia State University’s Risk Management Foundation |

  30. Other Current Directors

    | | | | | | | EXPERIENCE | | | | •From 1991 to 2005, served as Chief Executive Officer and Chairman of OSI Restaurant Partners, Inc. •From 1988 to 1991, was the co-founder, Chairman, and Chief Executive Officer of Outback Steakhouse | | | | EDUCATION | | | Chris Sullivan | | | | | •BS in Business and Economics, University of Kentucky | | | | OTHER PROFESSIONAL AND CHARITABLE AFFILIATIONS | | | Lead Independent Director | | | | | •Co-Chair, Consul Partners LLC •Past Chairman, Florida Council of 100 •Chairman, Arise Alliance Institute, a PTSD focused non-profit •Board Member and Executive Committee Member, Horatio Alger Association •Board Member, The First Tee of Tampa Bay and Copperhead Charities | | | Age: 78 | | | | Director Since: September 2019 (Independent) | | | | Committees: •Compensation •Executive •Nominating and Corporate Governance | |

  31. Other Current Directors

    | 10 | 2026 Proxy Statement | |

  32. Other Current Directors

    | TABLE OF CONTENTS | PROPOSAL NO. 1 |

  33. Other Current Directors

    | | | | | | | EXPERIENCE | | | | •From 2013 to 2017, served as President of Sales Strategy and Sales Operations at United Parcel Service Inc. •From 1984 to 2017, served in various roles at United Parcel Service Inc., including U.S. Director of Sales and Vice President of Sales | | | | EDUCATION | | | Myron Williams | | | | | •MBA, Florida Metropolitan University •BA in Business Administration, Albany State University | | | Age: 66 | | | | | OTHER PROFESSIONAL AND CHARITABLE AFFILIATIONS | | | Director Since: January 2022 (Independent) | •Chairman of the Board, Atlanta Public Schools CTAE Board •Advisory Board Member, PackageX •Vice-Chair of the Board, The MARCH Foundation •Board Member, Albert W. Smith Scholarship Committee •Previously served as Board Member, Center for Advance Logistics Management Board at Albany State University | | | Committees: •Compensation •Nominating and Corporate Governance | |

  34. Other Current Directors

    | | 2026 Proxy Statement | 11 |

  35. Other Current Directors

    | PROPOSAL NO. 1 | TABLE OF CONTENTS |

  36. Director Compensation

    Director Compensation The Compensation Committee, based in part on the advice of its independent compensation consultant, periodically reviews the annual retainer paid to non-employee directors and approves adjustments, as appropriate. In November 2024, the Compensation Committee reviewed director compensation for 2025, including consideration of the compensation practices of the boards of relevant peer companies and the general market, as well as a study by its independent consultant, which was prepared at the request of the Compensation Committee. After review, the Compensation Committee approved total compensation for our non-employee directors to be increased to align with median compensation for our peer group. Prior to the changes taking effect for 2025, the last time director compensation was adjusted was 2021.

  37. Director Compensation

    | Compensation Structure for Directors(1) | Amount ($) | | Annual Board Retainer | | | Cash | 105,000 | | Stock(2) | 105,000 | | Lead Independent Director Retainer | 25,000 | | Annual Audit Committee Chair Retainer | 20,000 | | Annual Compensation Committee Chair Retainer | 15,000 | | Annual Nominating and Corporate Governance Committee Chair Retainer | 15,000 | | Annual Technology and Cyber Risk Committee Chair Retainer | 15,000 |

  38. Director Compensation

    1.Cash retainers are paid in quarterly installments. 2.Granted as Class A common stock in quarterly installments. The number of shares is determined based on the closing price per share of Class A common stock on the last trading day before the beginning of the applicable fiscal quarter, rounded up to the nearest whole share. Members of our Board of Directors are also eligible for reimbursement for reasonable travel and other out-of-pocket expenses for meeting attendance. Directors do not receive per-meeting fees, either for Board meetings or Committee meetings. Non-employee directors are not entitled to retirement benefits, incentive compensation or perquisites.

  39. Director Compensation

    | | 2026 Proxy Statement | 19 |

  40. Director Compensation

    | CORPORATE GOVERNANCE | TABLE OF CONTENTS |

  41. Director Compensation

    The table below summarizes the compensation of all of our non-employee directors and our Board Chair for fiscal year 2025. We do not provide directors who are colleagues with additional compensation for their service as directors. Mr. Sparks is not included in the table below given he joined the Board in January 2026.

  42. Director Compensation

    | Name | Fees Earned or Paid in Cash ($) | Stock Awards(1) ($) | All Other Compensation ($) | Total ($) | | Lowry Baldwin(2) | — | — | 689,585 | 689,585 | | Jay Cohen | 105,000 | 103,587 | — | 208,587 | | Joseph Kadow | 120,000 | 103,587 | — | 223,587 | | Barbara Matas | 125,000 | 103,587 | — | 228,587 | | Sathish Muthukrishnan | 120,000 | 103,587 | — | 223,587 | | Sunita Parasuraman | 105,000 | 103,587 | — | 208,587 | | Ellyn Shook | 120,000 | 103,587 | — | 223,587 | | Chris Sullivan | 130,000 | 103,587 | — | 233,587 | | Myron Williams | 105,000 | 103,587 | — | 208,587 |

  43. Director Compensation

    1.The amounts shown represent the grant date fair value of these awards as computed in accordance with Accounting Standards Codification (“ASC”) Topic 718, Compensation (“ASC Topic 718”). For a discussion of valuation assumptions used to determine the grant date fair value of these awards, see Note 17 to our audited consolidated financial statements for the fiscal year ended December 31, 2025 included in our Annual Report on Form 10-K filed with the SEC on February 26, 2026. Stock awards were issued as 2,744 fully vested shares of Class A common stock for each of Mr. Cohen, Mr. Kadow, Ms. Matas, Mr. Muthukrishnan, Ms. Parasuraman, Ms. Shook, Mr. Sullivan and Mr. Williams. 2.All other compensation paid to Mr. Lowry Baldwin in 2025 represents (i) salary of $125,000 unrelated to Board service and (ii) risk advisor commissions of $564,585.

  44. Executive Compensation Policies and Practices

    | What We Do | | | | Pay for Performance. A large portion of our NEOs’ target total direct compensation is directly linked to the Company’s performance. | | | Compensation Risk Assessment. Our executive compensation program reflects an appropriate mix of compensation elements, balancing short-term and long-term performance objectives, cash and equity compensation, and risks and rewards. | | | Rigorous Performance Goals. We establish rigorous performance goals for our annual incentive plan and performance-based restricted stock unit programs that are approved by the Compensation Committee and reflect strong organic growth performance relative to industry norms. The maximum performance goals are set at levels that represent significant outperformance versus target, while threshold performance goals still represent meaningful year-over-year growth and are competitive with the historical performance of our market peers. | | | Performance-Based Compensation. Our executive compensation program is designed such that an appropriate portion of executive compensation is "at risk," which we believe motivates our executive team to deliver superior results on behalf of our shareholders. | | | Stock Ownership Guidelines. We have robust stock ownership guidelines that apply to our directors, officers, and executive leadership team to align their interests with those of our shareholders. | | | Compensation Clawback Policy. We have a clawback policy that applies to incentive compensation for our officers and executive leadership team. | | | Multi-Year and Performance-Based Vesting Requirements. Under the long-term incentive award plan approved by our Compensation Committee relating to the 2025 executive compensation program, all equity-based incentive awards granted to our NEOs have multi-year vesting conditions to promote retention. Performance share units (PSUs) granted to our NEOs in 2025 cliff-vest after three years, and no portion of the PSUs vest unless the relevant performance metrics are achieved, consistent with current market practice and our retention objectives. | | | Annual Say-on-Pay. We request the advisory vote of our shareholders on the compensation of our NEOs annually. | | | Independent Compensation Consultant. Our Compensation Committee engaged an independent compensation consultant to assist with the design of the 2025 executive compensation programs. | | | Annual Executive Compensation Review. Our Compensation Committee conducts an annual review of compensation for our NEOs and a review of compensation-related risks. | | | At Will Employment. We employ our NEOs at will. |

  45. Identifying Peer Companies and Conducting Comparative Market Analysis

    Identifying Peer Companies and Conducting Comparative Market Analysis With guidance from our independent compensation consultant, the Compensation Committee reviews and approves a peer group annually for use in conducting competitive market benchmarking for the compensation of our NEOs. This peer group is comprised of companies that are either direct competitors of Baldwin or in the same or similar industry as Baldwin, with comparable roles to our NEOs. The Compensation Committee may adjust the peer group composition as necessary, taking into account changes in both our business and the businesses of the companies in the compensation peer group. The peer group is used to provide meaningful insight into current pay practices and pay levels as well as overall compensation trends that are being utilized to attract and retain top talent. The Compensation Committee does not target compensation decisions or levels to a specific percentile or other absolute measures related to comparison group data, but does periodically review comparative market assessments of the pay practices of other companies with the goal of seeing that our executive compensation program remains competitive and aligned to our pay-for-performance philosophy.

  46. Identifying Peer Companies and Conducting Comparative Market Analysis

    | 38 | 2026 Proxy Statement | |

  47. Identifying Peer Companies and Conducting Comparative Market Analysis

    | TABLE OF CONTENTS | COMPENSATION DISCUSSION AND ANALYSIS |

  48. Identifying Peer Companies and Conducting Comparative Market Analysis

    In August 2024, the Compensation Committee identified groups of companies to serve as market reference points for compensation comparison purposes for 2025 and approved the Compensation Peer Group (as defined below). The Compensation Committee confirmed and ratified the Compensation Peer Group in February 2025. In October 2024 and February 2025, the Compensation Committee’s independent consultant presented analyses of our pay practices and executive compensation levels as compared to our established peer group (the “2025 Comparative Market Assessment”) to inform 2025 executive compensation decisions.

  49. Establishing Executive Compensation Pay Levels and Incentive Plans

    Establishing Executive Compensation Pay Levels and Incentive Plans With guidance from our independent compensation consultant, the Compensation Committee reviews and establishes the design and components of NEO compensation plans annually. The Compensation Committee takes into consideration the most recent comparative market assessment, company performance, and individual performance when setting compensation levels for the year. The Compensation Committee generally seeks to provide our NEOs with total Target compensation (i.e., the sum of base salary, Target annual incentives and Target long-term incentives) that is competitive relative to our compensation peer group companies for similar executive positions, with a substantial portion of total compensation being at risk and earned based on future performance. In addition, performance goals for our annual incentive plan and long-term equity incentive plan are established annually with target goals set at challenging levels based on the Company’s internal forecasting and budgeting processes and generally reflect strong organic growth performance relative to industry norms. The maximum performance goals are set at levels that represent outperformance, while threshold performance goals that fall short of target still represent meaningful year-over-year growth. The performance goals are approved by the Compensation Committee. The Compensation Committee considered, among other things, the 2025 Comparative Market Assessment when establishing the 2025 compensation framework for the NEOs. See “Overview of 2025 Compensation Framework” and “Compensation Details for Fiscal Year 2025” for more information on performance levels and metrics.

  50. ROLE OF THE COMPENSATION CONSULTANT

    ROLE OF THE COMPENSATION CONSULTANT The Compensation Committee selects and retains the services of its own independent compensation consultant and annually reviews the performance of such consultant. The Compensation Committee has retained Frederic W. Cook & Co., Inc. (“FW Cook”) to serve as its independent compensation consultant. During 2025, FW Cook provided no services to the Company other than services for the Compensation Committee, and worked with the Company’s management, as directed by the Compensation Committee, only on matters for which the Compensation Committee is responsible. The Compensation Committee considers the independence of the compensation consultant in accordance with SEC and Nasdaq rules, and affirmatively determined that FW Cook qualifies as independent under the applicable rules.

  51. ANNUAL BASE SALARY

    ANNUAL BASE SALARY Consistent with our pay-for-performance executive compensation strategy, salaries for all five of our NEOs are established below median of our compensation peer group, with all five of our NEOs below the 25th percentile compared to our compensation peer group for fiscal year 2025. Base salaries for our NEOs have not increased since 2022. However, see "Executive Compensation Update for 2026" regarding certain changes to base salaries in 2026. Refer to “Compensation Details for Fiscal Year 2025”—“Base Salary” for more details on the NEOs' base salaries.

  52. ANNUAL INCENTIVE PLAN

    ANNUAL INCENTIVE PLAN Our 2025 annual incentive plan (our “Annual Incentive Plan”) is a variable component of our compensation program that is designed to focus our NEOs on achieving superior performance over the short term against business objectives and financial results for the Company as a whole, while also rewarding them for the achievement of individual performance objectives. The Annual Incentive Plan provides payout opportunities in the form of cash and fully vested shares of Class A common stock (with the pay mix for a given year determined by our Compensation Committee) upon the achievement of certain pre-established performance metrics, including organic revenue growth, adjusted earnings before income taxes, depreciation and amortization ("EBITDA") growth, and personal objectives. The payout opportunity for our NEOs ranges from 50% of Target annual incentive opportunity at Threshold performance to 300% at Superior performance, with 100% of Target annual incentive opportunity at Target performance. By conditioning a large portion of our NEOs’ potential annual compensation on the Company’s achievement of clearly-defined metrics, we believe that we reinforce our strong pay-for-performance culture. Refer to “Compensation Details for Fiscal Year 2025”—“Annual Incentive Plan” for more details on our Annual Incentive Plan.

  53. LONG-TERM INCENTIVE PLAN

    LONG-TERM INCENTIVE PLAN Our 2025 long-term equity incentive plan (our “LTIP”) is a variable component of our compensation program that is designed to drive superior recurring performance over the long term and align the interests of our NEOs with those of our shareholders. We believe that long-term equity compensation is an effective way to provide a meaningful reward for appreciation in our stock price and create an “ownership culture” that motivates our NEOs to remain employed with us long-term. Our 2025 LTIP for our NEOs consists 100% of performance-based equity awards to further Baldwin's commitment to its pay-for-performance culture.

  54. Performance-Based Restricted Stock Units ("PSUs")

    Performance-Based Restricted Stock Units ("PSUs") The number of PSUs earned, if any, is determined based on the following performance goals (the “Performance Goals”), in each case as measured over the period from January 1, 2025 through December 31, 2027 (the “Performance Period”): (i) 50% based on our relative total shareholder return compared to the total shareholder return of our 2025 compensation peer group; and (ii) 50% based on our three-year adjusted diluted EPS compound annual growth rate. We define total shareholder return (“TSR”) as the annual total shareholder return for the Performance Period. Each NEO will earn a number of PSUs following the end of the Performance Period between 0% and 350% of each such NEO’s Target PSUs, with a Target of 100%, in each case depending on the level of achievement with respect to the Performance Goals. PSUs will be paid out to the NEOs on the date on which the Compensation Committee determines the number of such PSUs that were earned based on the Company's achievement of the applicable performance goals during the performance period, subject to the NEOs continued employment through such date. If our absolute total shareholder return for the Performance Period is negative, the maximum level of performance achievable with respect to the TSR performance goal for the PSUs will be Target. Refer to “Compensation Details for Fiscal Year 2025”—“LTIP” for more details on our LTIP.

  55. Performance-Based Restricted Stock Units ("PSUs")

    | 40 | 2026 Proxy Statement | |

  56. Performance-Based Restricted Stock Units ("PSUs")

    | TABLE OF CONTENTS | COMPENSATION DISCUSSION AND ANALYSIS |

  57. PEER COMPARISON GROUP

    PEER COMPARISON GROUP Our 2025 compensation peer group included 14 public companies, the majority of which are in either the insurance broker or property and casualty insurance services sectors. After consultation with FW Cook, the Compensation Committee approved the following compensation peer group for 2025 (the “Compensation Peer Group”):

  58. PEER COMPARISON GROUP

    | Peer Company | Business Focus | | Brown & Brown, Inc. | Insurance Brokers | | CBIZ, Inc. | Research and Consulting Services | | Employers Holdings, Inc. | Property and Casualty Insurance | | Erie Indemnity Company | Property and Casualty Insurance | | Goosehead Insurance, Inc. | Insurance Brokers | | Hagerty, Inc. | Insurance Brokers | | Kinsale Capital Group, Inc. | Property and Casualty Insurance | | Palomar Holdings, Inc. | Property and Casualty Insurance | | Primerica, Inc. | Life and Health Insurance | | RLI Corp. | Property and Casualty Insurance | | Ryan Specialty Holdings, Inc. | Insurance Brokers | | Safety Insurance Group, Inc. | Property and Casualty Insurance | | Selective Insurance Group, Inc. | Property and Casualty Insurance | | Stewart Information Services Corp. | Property and Casualty Insurance |

  59. RESULTS OF THE 2025 COMPARATIVE MARKET ASSESSMENT

    RESULTS OF THE 2025 COMPARATIVE MARKET ASSESSMENT The Compensation Committee examined the total direct compensation opportunity (base salary, annual cash incentives and long-term incentives) for each named executive officer, as well as individual elements of compensation. Data from the 2025 Comparative Market Assessment was used as a market reference for compensation decisions. The Compensation Committee does not target total compensation or any individual component thereof to a specific percentile of comparison group compensation. The 2025 Comparative Market Assessment showed the following with respect to base salary, target total annual cash compensation, which is equal to base salary plus target annual bonus (“TAC”), and target total direct compensation, which is TAC plus the target compensation under the LTIP (“TDC”):

  60. •Base Salary

    •Base Salary ◦The proposed (and ultimately approved) 2025 base salary for Mr. Baldwin was 59% below the median 2024 base salary for CEOs in the Compensation Peer Group; ◦the proposed (and ultimately approved) 2025 base salary for Messrs. Hale, Galbraith and Roche was 41-42% below the median 2024 base salaries for their respective peers in the Compensation Peer Group; and ◦the proposed (and ultimately approved) 2025 base salary for Mr. Cohen was 32% below the median 2024 base salary for his peers in the Third-Party Surveys.

  61. •TAC

    •TAC ◦The proposed (and ultimately approved) 2025 TAC for Mr. Baldwin was 9% below the median 2024 TAC for CEOs in the Compensation Peer Group; ◦the proposed (and ultimately approved) 2025 TAC for Mr. Hale was 4% above the median 2024 TAC for CFOs in the Compensation Peer Group; ◦the proposed (and ultimately approved) 2025 TAC for Messrs. Galbraith and Roche was 3% below the median 2024 TAC for their respective peers in the Compensation Peer Group; and ◦the proposed (and ultimately approved) 2025 TAC for Mr. Cohen was 2% above the median 2024 TAC for his peers in the Third-Party Surveys.

  62. ANNUAL INCENTIVE PLAN

    ANNUAL INCENTIVE PLAN The Compensation Committee established the following performance metrics and weighting of each for our NEOs for the 2025 Annual Incentive Plan:

  63. ANNUAL INCENTIVE PLAN

    | Organic Revenue Growth | Adjusted EBITDA | Personal Objectives | | 40% | 40% | 20% |

  64. ANNUAL INCENTIVE PLAN

    The Compensation Committee established the following performance level ranges for organic revenue growth and adjusted EBITDA under the 2025 Annual Incentive Plan:

  65. ANNUAL INCENTIVE PLAN

    | Performance Level | Threshold Performance | Target Performance | Superior Performance | | Organic Revenue Growth (%) | 7% | 10% | 16% | | Adjusted EBITDA ($) | 320,000,000 | 345,000,000 | 375,000,000 |

  66. ANNUAL INCENTIVE PLAN

    The Compensation Committee set personal objectives for each NEO under the 2025 Annual Incentive Plan, with the focus areas for each NEO described below.

  67. ANNUAL INCENTIVE PLAN

    | Name | Personal Objectives Focus Areas | | Trevor Baldwin | Firm reputation and culture; key strategic initiatives to deliver organic revenue growth and margin accretion; talent building, retention and senior leadership succession readiness; and refine 5-year strategic road map with a cascading plan for individual business segments | | Bradford Hale | Tracking operating and capital expenditures, particularly in information technology; cash flow analysis and forecasting; strategic leadership; capital markets execution and strategy; strategy to expand analyst coverage and cultivate investor relations; and succession readiness | | Daniel Galbraith | Leadership organization across IAS; integration, process and cost efficiencies; performance improvements and efficiency; retail finance function and forecasting; operations, product, technology and data strategies; and succession readiness | | Jim Roche | Technology and team needed to increase the pace of product release cycles; operational efficiencies; continue to grow prospects for Westwood business; new and emerging products; alternative capacity; analyze and execute on opportunistic partnership opportunities; and succession readiness | | Seth Cohen | Legal function efficiency and quality improvements; information technology and cybersecurity collaboration amongst segments; develop legal talent and key business relationships; drive efficient legal spend; mitigate key risks across the firm; and succession readiness |

  68. ANNUAL INCENTIVE PLAN

    | 44 | 2026 Proxy Statement | |

  69. ANNUAL INCENTIVE PLAN

    | TABLE OF CONTENTS | COMPENSATION DISCUSSION AND ANALYSIS |

  70. ANNUAL INCENTIVE PLAN

    Each NEO's Target Annual Incentive Plan opportunity for fiscal year 2025 is set forth in the table below:

  71. ANNUAL INCENTIVE PLAN

    | Name | Target Annual Incentive Plan Opportunity ($) | | Trevor Baldwin | 1,600,000 | | Bradford Hale | 675,000 | | Daniel Galbraith | 675,000 | | Jim Roche | 675,000 | | Seth Cohen | 450,000 |

  72. ANNUAL INCENTIVE PLAN

    The Compensation Committee set the following payout ranges for our NEOs as a percentage of the Target Annual Incentive Plan opportunity based on the achievement of the metrics above.

  73. ANNUAL INCENTIVE PLAN

    | Threshold | Target | Superior | | 50% | 100% | 300% |

  74. ANNUAL INCENTIVE PLAN

    The Compensation Committee reviewed the actual performance under the 2025 Annual Incentive Plan of each financial performance measure against Target performance to determine the percentage of Target achieved for each as follows:

  75. ANNUAL INCENTIVE PLAN

    | Performance Level | Target Performance | Actual Performance | Performance % of Target Achieved(1) | | Organic Revenue Growth | 10% | 7% | 55% | | Adjusted EBITDA | $345,000,000 | $341,472,000 | 93% |

  76. ANNUAL INCENTIVE PLAN

    1.Based on Threshold, Target and Superior payouts of 50%, 100% and 300%, respectively. For their contribution in furthering their respective personal objective focus areas listed above, each NEO described above achieved a level of performance between Target and Superior for their respective personal objectives. The table below sets forth each NEO's actual Annual Incentive Plan payout amount for fiscal year 2025, which was made 100% in fully vested shares of Class A common stock consistent with the Company's philosophy on ownership culture and executive team alignment with our shareholders.

  77. ANNUAL INCENTIVE PLAN

    | Name | 2025 Annual Incentive Plan Payout ($) | Payout as a Percent of Target Annual Incentive Plan Opportunity (%) | | Trevor Baldwin | 1,785,000 | 111.6% | | Bradford Hale | 672,188 | 99.6% | | Daniel Galbraith | 670,500 | 99.3% | | Jim Roche | 807,188 | 119.6% | | Seth Cohen | 448,125 | 99.6% |

  78. ANNUAL INCENTIVE PLAN

    | | 2026 Proxy Statement | 45 |

  79. ANNUAL INCENTIVE PLAN

    | COMPENSATION DISCUSSION AND ANALYSIS | TABLE OF CONTENTS |

  80. LTIP

    LTIP As discussed above, based on the Compensation Committee’s review and the recommendations of FW Cook, our 2025 LTIP for our NEOs consists 100% of performance-based equity awards in the form of PSUs. The PSUs are settled in shares of our Class A common stock, the number of which will depend on the level of performance achieved with respect to applicable Performance Goals during the Performance Period. The table below sets forth the 2025 LTIP award grant values (at Target) that were approved by the Compensation Committee for each NEO.

  81. LTIP

    | Name | Target LTIP Award Grant Value ($) | | Trevor Baldwin | 2,000,000 | | Bradford Hale | 900,000 | | Daniel Galbraith | 900,000 | | Jim Roche | 900,000 | | Seth Cohen | 400,000 |

  82. LTIP

    The Target LTIP award grant value for each of our NEOs was granted as PSUs. The number of Target PSUs granted was determined by dividing the Target award grant value by a price per share equal to the average of the volume weighted average prices for a share of our Class A common stock on the Nasdaq across the 30 consecutive calendar days immediately prior to the grant date.

  83. PSUs

    PSUs The number of shares earned pursuant to PSUs (representing 100% of the Target LTIP award grant value for each of our NEOs) will be determined based on the following performance metrics (and weighting of each metric), in each case as measured over the Performance Period:

  84. PSUs

    | Performance Metric | | 50% of Target Number of PSUs Based on Relative TSR v. Compensation Peer Group | | 50% of Target Number of PSUs Based on 3-year Adjusted Diluted EPS Compound Annual Growth Rate |

  85. PSUs

    Relative TSR v. Compensation Peer Group means the Company’s compound annual total shareholder return for the Performance Period, compared to the compound annual total shareholder return of our Compensation Peer Group for the same period. The Company uses the average closing price for the last 30 trading days immediately prior to the beginning of the Performance Period and the average closing price for the last 30 trading days at the end of the Performance Period, as adjusted for dividends and stock splits as applicable. The 3-year adjusted diluted EPS compound annual growth rate (“CAGR”) means the Company's average annual adjusted diluted EPS growth during the three-year Performance Period.

  86. PSUs

    | 46 | 2026 Proxy Statement | |

  87. PSUs

    | TABLE OF CONTENTS | COMPENSATION DISCUSSION AND ANALYSIS |

  88. PSUs

    The Compensation Committee set the following performance level ranges applicable to each TSR and CAGR Performance Goal and the percentage of PSUs to be earned based on the Company's level of achievement of the applicable TSR and CAGR Performance Goal:

  89. PSUs

    | | | Relative TSR Portion (50% of PSU Award) | CAGR Portion (50% of PSU Award) | Percentage of PSUs Earned Based on Performance Goal | | Name | Performance Level | Relative TSR v. Compensation Peer Group | 3-year Adjusted Diluted EPS CAGR | | | Trevor Baldwin Bradford Hale Daniel Galbraith Jim Roche Seth Cohen | Threshold | 40th Percentile | 10% | 50% | | | Target | 55th Percentile | 15% | 100% | | | Superior | 90th Percentile | 20% | 350% |

  90. PSUs

    As illustrated above, for the Performance Period, with respect to the TSR Performance Goal, performance at the Threshold level will result in 50% of the Target number of PSUs being earned with respect to such Performance Goal; performance at the Target level will result in 100% of the Target number of PSUs being earned; performance at or above the Superior level will result in a maximum of 350% of the Target number of PSUs being earned for each of our NEOs. Performance below the Threshold level will result in no PSUs being earned with respect to such Performance Goal. Performance between the foregoing levels for each Performance Goal will be calculated on the basis of linear interpolation. If the Company’s TSR for the Performance Period is negative, the maximum level of performance achievable under the TSR Performance Goal is Target. The table below sets forth the grant values of PSUs for each NEO for the Performance Period, at each of Threshold, Target and Superior performance.

  91. PSUs

    | Name | Threshold PSU Award Grant Value (50% of Target) ($) | Target PSU Award Grant Value ($) | Superior PSU Award Grant Value (350% of Target) ($) | | Trevor Baldwin | 1,000,000 | 2,000,000 | 7,000,000 | | Bradford Hale | 450,000 | 900,000 | 3,150,000 | | Daniel Galbraith | 450,000 | 900,000 | 3,150,000 | | Jim Roche | 450,000 | 900,000 | 3,150,000 | | Seth Cohen | 200,000 | 400,000 | 1,400,000 |

  92. PSUs

    The following sets forth the aggregate number of PSUs our NEOs would earn, assuming achievement of the Target level of performance of both the TSR and CAGR Performance Goals over the Performance Period:

  93. PSUs

    | Name | Target Number of PSUs (#) | | Trevor Baldwin | 49,014 | | Bradford Hale | 22,056 | | Daniel Galbraith | 22,056 | | Jim Roche | 22,056 | | Seth Cohen | 9,802 |

  94. PSUs

    | | 2026 Proxy Statement | 47 |

  95. PSUs

    | COMPENSATION DISCUSSION AND ANALYSIS | TABLE OF CONTENTS |

  96. Results for 2023 LTIP Performance Share Awards

    Results for 2023 LTIP Performance Share Awards The Compensation Committee established the following relative TSR and organic revenue growth compound annual growth rate goals for our 2023 LTIP PSUs for the three-year performance period ending December 31, 2025:

  97. Results for 2023 LTIP Performance Share Awards

    | | | Relative TSR Portion (60% of PSU Award) | | CAGR Portion (40% of PSU Award) | Percentage of PSUs Earned Based on Performance Goal (%) | | Name | Performance Level | Relative TSR v. Compensation Peer Group (50% of Relative TSR Portion) | Relative TSR v. Russell 3000 Growth Index (50% of Relative TSR Portion) | 3-year Organic Revenue Growth CAGR (%) | | | Trevor Baldwin Bradford Hale Daniel Galbraith Jim Roche | Threshold | 40th Percentile | 40th Percentile | 7% | 50% | | | Target | 55th Percentile | 55th Percentile | 10% | 100% | | | Superior | 90th Percentile | 90th Percentile | 20% | 350% | | Seth Cohen | Threshold | 40th Percentile | 40th Percentile | 7% | 50% | | | Target | 55th Percentile | 55th Percentile | 10% | 100% | | | Superior | 75th Percentile | 75th Percentile | 15% | 250% |

  98. Results for 2023 LTIP Performance Share Awards

    In February 2026, the Committee determined that the relative TSR goals versus the performance of the 2023 compensation peer group and the Russell 3000 Growth Index were not achieved, and that the Company’s 3-year organic revenue growth CAGR was 14.1%, which resulted in a payout percentage of 81% of the target number of 2023 PSUs for Messrs. Baldwin, Hale, Galbraith and Roche, and 89% for Mr. Cohen. As a result, our NEOs earned the number of 2023 PSUs set forth below, all of which were paid out in connection with the vesting of these awards in the first quarter of 2026:

  99. Results for 2023 LTIP Performance Share Awards

    | Name | Target Number of PSUs (#) | Number of PSUs Attained (#) | | Trevor Baldwin | 81,054 | 65,655 | | Bradford Hale | 36,474 | 29,544 | | Daniel Galbraith | 36,474 | 29,544 | | Jim Roche | 36,474 | 29,544 | | Seth Cohen | 11,397 | 10,167 |

  100. Executive Compensation Update for 2026

    In addition, in consultation with our compensation consultant, the Compensation Committee reviewed the performance metrics and weightings for the 2026 annual incentive plan opportunity (the "2026 AIP"). Based on this review, the Compensation Committee approved updates to the 2026 AIP to place greater focus on company performance over personal objectives. First, organic revenue growth and adjusted EBITDA growth will be weighted 50% each instead of 40% each as was the case in 2025. Second, the 20% weighting for personal objectives was eliminated in favor of an individual performance modifier (the "IPM"). The IPM gives the Compensation Committee the express right, but not the obligation, to add or subtract up to 30% of an NEO's 2026 AIP target opportunity to his or her final payout percentage when an NEO has exhibited significant over or underperformance during the year as the case may be. Payout percentages of an NEO's 2026 AIP target opportunity cannot be reduced below 0% or increased above the maximum payout for superior performance under the 2026 AIP. The Compensation Committee believes that the IPM will allow the committee to reasonably ensure that an NEO’s 2026 AIP payout appropriately reflects his or her contributions to the Company’s performance during the year.

  101. Compensation Risk Assessment

    Compensation Risk Assessment The Compensation Committee believes that the design, implementation and governance of our executive compensation program are consistent with high standards of risk management. Our executive compensation program reflects an appropriate mix of compensation elements, balancing short-term and long-term performance objectives, cash and equity compensation, and risks and rewards. •The compensation framework used for making compensation decisions is multi-faceted as it incorporates multiple metrics over varying time periods and is subject to the application of informed judgment by the Compensation Committee. •To further ensure that the interests of our NEOs are aligned with those of our shareholders, a significant portion of executive officer long-term incentive compensation is awarded as equity subject to vesting requirements. PSUs typically cliff-vest and settle after a three-year period based on achievement of applicable performance goals at the end of a three-year period. •Executives are expected to meet the applicable stock ownership guidelines described under “Corporate Governance”—“Stock Ownership Guidelines.” •Incentive compensation is subject to the Clawback Policy described under “Corporate Governance”—“Clawback Policy.” Based on these features, we believe our executive compensation program effectively (i) ensures that our compensation opportunities do not encourage excessive risk taking, (ii) keeps our NEOs focused on the creation of long-term, sustainable value for our shareholders and (iii) provides competitive and appropriate levels of compensation over time.

  102. Summary Compensation Table

    Summary Compensation Table The below summary compensation table contains compensation paid to our NEOs during the years ended December 31, 2025, 2024 and 2023.

  103. Summary Compensation Table

    | Name and Position | Year | Salary(1) ($) | Bonus(2) ($) | Stock Awards(3) ($) | Non-equity Incentive Plan Compensation(4) ($) | All Other Compensation(5) ($) | Total ($) | | Trevor Baldwin Chief Executive Officer | 2025 | 400,000 | — | 3,068,032 | 1,785,000 | — | 5,253,032 | | | 2024 | 400,000 | — | 3,137,414 | 2,170,000 | — | 5,707,414 | | | 2023 | 400,000 | — | 3,828,490 | 2,169,600 | — | 6,398,090 | | Bradford Hale Chief Financial Officer | 2025 | 300,000 | — | 1,380,595 | 672,188 | 20,240 | 2,373,023 | | | 2024 | 300,000 | — | 1,411,832 | 1,083,593 | 20,000 | 2,815,425 | | | 2023 | 300,000 | — | 1,722,798 | 1,122,600 | 20,000 | 3,165,398 | | Daniel Galbraith President, The Baldwin Group and CEO, Retail Brokerage Operations | 2025 | 300,000 | — | 1,380,595 | 670,500 | 22,300 | 2,373,395 | | | 2024 | 300,000 | 750,000 | 1,411,832 | 1,099,593 | 23,800 | 3,585,225 | | | 2023 | 300,000 | — | 1,722,798 | 1,104,600 | 21,500 | 3,148,898 | | Jim Roche(6) President, The Baldwin Group and CEO, Underwriting, Capacity & Technology Operations | 2025 | 300,000 | — | 1,380,595 | 807,188 | 12,000 | 2,499,783 | | | 2024 | 300,000 | — | 1,411,832 | 1,069,593 | 11,961 | 2,793,386 | | Seth Cohen(6) General Counsel | 2025 | 300,000 | — | 613,556 | 448,125 | 11,841 | 1,373,522 | | | 2024 | 300,000 | — | 492,602 | 571,670 | 11,539 | 1,375,811 |

  104. Summary Compensation Table

    1.Mr. Roche's salary for 2024 includes $170,000 paid throughout the year and $130,000 paid in pro rata quarterly installments. 2.For 2024, the amount shown represents a $750,000 bonus paid to Mr. Galbraith in recognition of his promotion to President, The Baldwin Group and CEO, Retail Brokerage Operations. 3.For 2025, the amounts shown represent the grant date fair value of PSUs (with a performance period of January 1, 2025 to December 31, 2027) awarded to our NEOs under the LTIP, as follows: Mr. Baldwin—49,014 PSUs; Mr. Hale—22,056 PSUs Mr. Galbraith—22,056 PSUs; Mr. Roche—22,056 PSUs; and Mr. Cohen—9,802 PSUs. For 2024, the amounts shown represent the grant date fair value of PSUs (with a performance period of January 1, 2024 to December 31, 2026) and RSAs (vesting ratably over 5 years) awarded to our NEOs under the LTIP, as follows: Mr. Baldwin—68,138 PSUs; Mr. Hale—30,662 PSUs; Mr. Galbraith—30,662 PSUs; Mr. Roche—30,662 PSUs; and Mr. Cohen—10,220 PSUs and 3,406 RSAs. For 2023, the amounts shown represent the grant date fair value of PSUs (with a performance period of January 1, 2023 to December 31, 2025) awarded to our NEOs under the LTIP, as follows: Mr. Baldwin—81,054 PSUs; Mr. Hale—36,474 PSUs; and Mr. Galbraith—36,474 PSUs. For a discussion of valuation assumptions used to determine the grant date fair value of these awards, see Note 17 to our audited consolidated financial statements for the year ended December 31, 2025 included in our Annual Report on Form 10-K filed with the SEC on February 26, 2026. 4.For 2025, the amounts shown represent the dollar value of bonuses in respect of 2025 performance paid to our NEOs in 2026 in fully vested shares of our Class A common stock issued under our Omnibus Plan as follows: Mr. Baldwin—76,972 shares; Mr. Hale—28,986 shares; Mr. Galbraith—28,913 shares; Mr. Roche—34,807 shares; and Mr. Cohen—19,324 shares. For 2024, the amounts shown represent the dollar value of bonuses in respect of 2024 performance paid to our NEOs in 2025 in fully vested shares of our Class A common stock issued under our Omnibus Plan, as follows: Mr. Baldwin—54,290 shares; Mr. Hale—27,110 shares; Mr. Galbraith—27,510 shares; Mr. Roche—26,759 shares; and Mr. Cohen—14,302 shares. For 2023, the amounts shown represent the dollar value of bonuses in respect of 2023 performance paid to our NEOs in 2024 in fully vested shares of our Class A common stock issued under our Omnibus Plan, as follows: Mr. Baldwin—73,917 shares; Mr. Hale—38,246 shares; and Mr. Galbraith—37,633 shares. 5.For 2025, the amounts shown represent (i) tax preparation services paid for by Baldwin Holdings on behalf of Messrs. Hale and Galbraith (in their capacity as Baldwin Holdings Members) in respect of 2024 taxes at a cost of $8,240 and $10,300, respectively; and (ii) matching contributions under our 401(k) Plan for Messrs. Hale, Galbraith, Roche and Cohen of $12,000, $12,000, $12,000 and $11,841, respectively. 6.Only 2024 and 2025 compensation is required to be disclosed for Messrs. Roche and Cohen as 2024 was their first year as NEOs.

  105. Summary Compensation Table

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  106. Summary Compensation Table

    | COMPENSATION TABLES | TABLE OF CONTENTS |

  107. Grants of Plan Based Awards for Fiscal Year 2025

    Grants of Plan Based Awards for Fiscal Year 2025 The following table provides information regarding all incentive and stock awards we granted to our NEOs for 2025:

  108. Grants of Plan Based Awards for Fiscal Year 2025

    | Name | Grant Date | Estimated future payouts under non-equity incentive plan awards | | | Estimated future payouts under equity incentive plan awards | | | Grant date fair value of stock and option awards(1) ($) | | | | Threshold ($) | Target ($) | Maximum ($) | Threshold (#) | Target (#) | Maximum (#) | | | Trevor Baldwin | | | | | | | | | | 2025 Annual Bonus | | 800,000 | 1,600,000 | 4,800,000 | | | | | | PSUs | 2/28/2025 | | | | 24,506 | 49,014 | 171,552 | 3,068,032 | | Bradford Hale | | | | | | | | | | 2025 Annual Bonus | | 337,500 | 675,000 | 2,025,000 | | | | | | PSUs | 2/28/2025 | | | | 11,028 | 22,056 | 77,198 | 1,380,595 | | Daniel Galbraith | | | | | | | | | | 2025 Annual Bonus | | 337,500 | 675,000 | 2,025,000 | | | | | | PSUs | 2/28/2025 | | | | 11,028 | 22,056 | 77,198 | 1,380,595 | | Jim Roche | | | | | | | | | | 2025 Annual Bonus | | 337,500 | 675,000 | 2,025,000 | | | | | | PSUs | 2/28/2025 | | | | 11,028 | 22,056 | 77,198 | 1,380,595 | | Seth Cohen | | | | | | | | | | 2025 Annual Bonus | | 225,000 | 450,000 | 1,350,000 | | | | | | PSUs | 2/28/2025 | | | | 4,900 | 9,802 | 34,310 | 613,556 |

  109. Grants of Plan Based Awards for Fiscal Year 2025

    1.Represents the grant date fair value of stock awards granted during 2025, calculated in accordance with ASC Topic 718.

  110. Grants of Plan Based Awards for Fiscal Year 2025

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  111. Grants of Plan Based Awards for Fiscal Year 2025

    | TABLE OF CONTENTS | COMPENSATION TABLES |

  112. Outstanding Equity Awards at 2025 Fiscal Year-End

    Outstanding Equity Awards at 2025 Fiscal Year-End The following table provides information on the holdings of unvested stock awards by our NEOs at December 31, 2025.

  113. Outstanding Equity Awards at 2025 Fiscal Year-End

    | Name | | | Stock Awards | | | | | | Grant Date | Type of Equity | Number of shares or units of stock that have not vested (#) | Market value of shares or units of stock that have not vested(1) ($) | Equity incentive plan awards: number of unearned shares, units or other rights that have not vested (#) | Equity incentive plan awards: market or payout value of unearned shares, units or other rights that have not vested(1) ($) | | Trevor Baldwin | 5/3/2021 | RSA | — | — | 1,705(2) | 40,971 | | | 3/15/2022 | RSA | — | — | 6,594(3) | 158,454 | | | 2/22/2023 | PSU | — | — | 137,794(4) | 3,311,190 | | | 4/1/2024 | PSU | — | — | 136,278(5) | 3,274,760 | | | 2/28/2025 | PSU | — | — | 36,760(6) | 883,343 | | Bradford Hale | 4/1/2021 | RSA | 25,000(7) | 600,750 | — | — | | | 5/3/2021 | RSA | — | — | 1,023(2) | 24,583 | | | 3/15/2022 | RSA | — | — | 2,826(3) | 67,909 | | | 2/22/2023 | PSU | — | — | 62,007(4) | 1,490,028 | | | 4/1/2024 | PSU | — | — | 61,324(5) | 1,473,616 | | | 2/28/2025 | PSU | — | — | 16,542(6) | 397,504 | | Daniel Galbraith | 5/3/2021 | RSA | — | — | 1,023(2) | 24,583 | | | 3/15/2022 | RSA | — | — | 2,826(3) | 67,909 | | | 2/22/2023 | PSU | — | — | 62,007(4) | 1,490,028 | | | 4/1/2024 | PSU | — | — | 61,324(5) | 1,473,616 | | | 2/28/2025 | PSU | — | — | 16,542(6) | 397,504 | | Jim Roche | 3/15/2022 | RSA | — | — | 2,308(3) | 55,461 | | | 2/22/2023 | PSU | — | — | 62,007(4) | 1,490,028 | | | 4/1/2024 | PSU | — | — | 61,324(5) | 1,473,616 | | | 2/28/2025 | PSU | — | — | 16,542(6) | 397,504 | | Seth Cohen | 3/15/2022 | RSA | — | — | 1,412(3) | 33,930 | | | 2/22/2023 | RSA | — | — | 2,279(8) | 54,764 | | | 2/22/2023 | PSU | — | — | 14,816(4) | 356,028 | | | 4/1/2024 | RSA | — | — | 2,724(9) | 65,458 | | | 4/1/2024 | PSU | — | — | 15,331(5) | 368,404 | | | 2/28/2025 | PSU | — | — | 7,351(6) | 176,645 |

  114. Outstanding Equity Awards at 2025 Fiscal Year-End

    1.The amounts shown are based on the closing market price of our Class A common stock on December 31, 2025, which was $24.03 per share. 2.These RSAs vested on March 15, 2026.

  115. Outstanding Equity Awards at 2025 Fiscal Year-End

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  116. Outstanding Equity Awards at 2025 Fiscal Year-End

    | COMPENSATION TABLES | TABLE OF CONTENTS |

  117. Outstanding Equity Awards at 2025 Fiscal Year-End

    3.These RSAs vested one-half on March 15, 2026 with the remaining RSAs to vest on March 15, 2027, subject to the NEO's continued employment. 4.The amount shown represents the number of PSUs that could have been earned during the three-year performance period of January 1, 2023 to December 31, 2025 representing (i) payouts at the threshold performance level for the relative TSR v. the 2023 compensation peer group PSUs and the relative TSR v. the Russell 3000 Growth Index PSUs and (ii) payouts at the superior performance level for the 3-year organic revenue growth CAGR PSUs. PSUs earned following the end of the performance period were as follows: Mr. Baldwin—65,655 PSUs; Mr. Hale—29,544 PSUs Mr. Galbraith—29,544 PSUs; Mr. Roche—29,544 PSUs; and Mr. Cohen—10,167 PSUs, which were paid out on February 23, 2026. 5.The amount shown represents the number of PSUs that could be earned during the three-year performance period of January 1, 2024 to December 31, 2026 representing (i) payouts at the superior performance level for the relative TSR v. the 2024 compensation peer group PSUs and (ii) payouts at the threshold performance level for the 3-year adjusted diluted EPS CAGR PSUs. Although performance for the PSUs was either above or below target when measured as of December 31, 2025, the results could change during the remainder of the performance period. The number of PSUs that are earned following the end of the performance period will be paid out on the applicable date on which the Compensation Committee determines the number of such PSUs earned, with any such payment subject to recoupment and/or forfeiture should the NEO's continued employment cease on or before March 15, 2027. 6.The amount shown represents the number of PSUs that could be earned during the three-year performance period of January 1, 2025 to December 31, 2027 representing (i) payouts at the threshold performance level for the relative TSR v. the 2025 compensation peer group PSUs and (ii) payouts at the target performance level for the 3-year adjusted diluted EPS CAGR PSUs. Although performance for the PSUs was either below or at target when measured as of December 31, 2025, the results could change during the remainder of the performance period. The number of PSUs that are earned following the end of the performance period will be paid out on the applicable date on which the Compensation Committee determines the number of such PSUs earned, subject to the NEOs continued employment through such date. 7.These RSAs vested on April 1, 2026. 8.These RSAs vested one-third on March 15, 2026 with the remaining RSAs to vest in equal annual installments over two years beginning March 15, 2027, subject to Mr. Cohen's continued employment through the vesting date. 9.These RSAs vested one-quarter on March 15, 2026 with the remaining RSAs to vest in equal annual installments over three years beginning March 15, 2027, subject to Mr. Cohen's continued employment through the vesting date.

  118. Options Exercised and Stock Vested for Fiscal Year 2025

    Options Exercised and Stock Vested for Fiscal Year 2025

  119. Options Exercised and Stock Vested for Fiscal Year 2025

    | | Stock Awards | | | Name | Number of Shares Acquired on Vesting (#) | Value Realized on Vesting(1) ($) | | Trevor Baldwin | 136,230 | 5,512,846 | | Bradford Hale | 62,518 | 2,527,866 | | Daniel Galbraith | 62,918 | 2,543,866 | | Jim Roche | 54,840 | 2,215,686 | | Seth Cohen | 33,185 | 1,341,921 |

  120. Options Exercised and Stock Vested for Fiscal Year 2025

    1.Calculated as the aggregate dollar amount realized upon the vesting of RSAs and other equity awards determined by multiplying the number of shares acquired on vesting by the closing market price of our Class A common stock on the respective vesting dates.

  121. Options Exercised and Stock Vested for Fiscal Year 2025

    | 54 | 2026 Proxy Statement | |

  122. Options Exercised and Stock Vested for Fiscal Year 2025

    | TABLE OF CONTENTS | COMPENSATION TABLES |

  123. Potential Payments Upon Termination or Change in Control

    Potential Payments Upon Termination or Change in Control Our NEOs are entitled to certain payments and/or other benefits upon qualifying terminations of employment and/or a change in control of the Company pursuant to The Baldwin Insurance Group Holdings, LLC Executive Severance and Change in Control Benefit Program (the “Severance Plan”).

  124. Pay Versus Performance

    Pay Versus Performance

  125. Pay Versus Performance Table

    Pay Versus Performance Table The following pay versus performance table contains information regarding compensation paid to our principal executive officer (“PEO”) and our other NEOs ("Non-PEO NEOs") during the five years ended December 31, 2025 (to the extent they served as our NEOs for such years), our total shareholder return and that of our peer group, and other measures of Baldwin's performance.

  126. Pay Versus Performance Table

    | | Summary Compensation Table Total for PEO(1) ($) | Compensation Actually Paid to PEO(2) ($) | Average Summary Compensation Table Total for Non-PEO NEOs(3) ($) | Average Compensation Actually Paid to Non-PEO NEOs(4) ($) | Value of Initial Fixed $100 Investment Based On: | | | Organic Revenue Growth(7) (%) | | Year | | | | | Total Shareholder Return(5) ($) | Peer Group Total Shareholder Return(6) ($) | Net Income (Loss) ($) | | | 2025 | 5,253,032 | (2,411,859) | 2,154,931 | (802,275) | 80.18 | 164.75 | (54,154,000) | 7% | | 2024 | 5,707,414 | 11,530,896 | 2,642,462 | 4,896,011 | 129.33 | 180.44 | (41,081,000) | 17% | | 2023 | 6,398,090 | 3,745,445 | 5,548,314 | 3,040,128 | 80.15 | 147.87 | (164,019,000) | 19% | | 2022 | 4,752,320 | 3,795,606 | 2,167,992 | (691,351) | 83.89 | 135.17 | (76,748,000) | 23% | | 2021 | 3,445,981 | 3,913,812 | 1,858,487 | 3,261,901 | 120.49 | 137.60 | (58,120,000) | 22% |

  127. Pay Versus Performance Table

    1.Summary compensation table total for PEO amounts represent those reported for Trevor Baldwin, our Chief Executive Officer, for each of the corresponding years in the “Total” column of the Summary Compensation Table. 2.Compensation actually paid to PEO represents that of Mr. Baldwin, which is computed in accordance with Item 402(v) of Regulation S-K and does not reflect total compensation actually realized or received. Compensation actually paid to PEO is calculated as follows for each of the years presented. Equity values are calculated in accordance with ASC Topic 718, and the valuation assumptions used to calculate fair values did not materially differ from those disclosed at the time of grant.

  128. Pay Versus Performance Table

    | Calculation of Compensation Actually Paid to PEO | 2025 ($) | 2024 ($) | 2023 ($) | 2022 ($) | 2021 ($) | | Summary Compensation Table Total | 5,253,032 | 5,707,414 | 6,398,090 | 4,752,320 | 3,445,981 | | Less: value of Stock Awards per the Summary Compensation Table | (3,068,032) | (3,137,414) | (3,828,490) | (2,453,920) | (1,344,981) | | Plus: year-end fair value of awards granted in covered fiscal year that are unvested at year-end | 1,235,888 | 4,913,771 | 2,546,549 | 2,291,676 | 1,812,812 | | Plus or minus: covered year change in fair value of awards granted in prior years that are unvested at year-end | (5,999,596) | 4,020,709 | (553,618) | (775,704) | — | | Plus or minus: covered year change in fair value through vest date of awards granted in prior years that vested in the covered fiscal year | 166,849 | 26,416 | (13,111) | (18,766) | — | | Less: prior year-end fair value of awards granted in prior years that failed to meet vesting in the covered fiscal year | — | — | (803,975) | — | — | | Compensation Actually Paid to PEO | (2,411,859) | 11,530,896 | 3,745,445 | 3,795,606 | 3,913,812 |

  129. Pay Versus Performance Table

    | 60 | 2026 Proxy Statement | |

  130. Pay Versus Performance Table

    | TABLE OF CONTENTS | PAY VERSUS PERFORMANCE |

  131. Pay Versus Performance Table

    3.Average summary compensation table total for Non-PEO NEOs is calculated as (i) the average summary compensation table total amounts for Messrs. Hale, Galbraith, Roche and Cohen for 2025 and 2024; and (ii) the average summary compensation table total amounts for Messrs. Hale and Galbraith, John Valentine and Kris Wiebeck for 2023, 2022 and 2021 (Messrs. Roche and Cohen's 2023, 2022 and 2021 compensation is not required to be disclosed because 2024 was their first year as NEOs). 4.Average compensation actually paid to Non-PEO NEOs is calculated as (i) the average amounts paid to Messrs. Hale, Galbraith, Roche and Cohen for 2025 and 2024; and (ii) the average amounts paid to Messrs. Hale, Galbraith, Valentine and Wiebeck for 2023, 2022 and 2021 (Messrs. Roche and Cohen's 2023, 2022 and 2021 compensation is not required to be disclosed because 2024 was their first year as NEOs). Compensation actually paid to non-PEO NEOs is computed in accordance with Item 402(v) of Regulation S-K and does not reflect total compensation actually realized or received. Compensation actually paid to non-PEO NEOs is calculated as follows for each of the years presented. Equity values are calculated in accordance with ASC Topic 718, and the valuation assumptions used to calculate fair values did not materially differ from those disclosed at the time of grant.

  132. Pay Versus Performance Table

    | Calculation of Compensation Actually Paid to Non-PEO NEOs | 2025 ($) | 2024 ($) | 2023 ($) | 2022 ($) | 2021 ($) | | Summary Compensation Table Total | 2,154,931 | 2,642,462 | 5,548,314 | 2,167,992 | 1,858,487 | | Less: value of Stock Awards per the Summary Compensation Table | (1,188,835) | (1,182,025) | (2,669,401) | (1,051,634) | (977,255) | | Plus: year-end fair value of awards granted in covered fiscal year that are unvested at year-end | 478,896 | 1,842,884 | 1,485,366 | 982,104 | 1,313,314 | | Plus or minus: covered year change in fair value of awards granted in prior years that are unvested at year-end | (2,307,221) | 1,558,528 | (245,240) | (1,712,535) | 1,319,326 | | Plus or minus: covered year change in fair value through vest date of awards granted in prior years that vested in the covered fiscal year | 59,954 | 34,162 | (137,999) | (1,077,278) | (251,971) | | Less: prior year-end fair value of awards granted in prior years that failed to meet vesting in the covered fiscal year | — | — | (940,912) | — | — | | Compensation Actually Paid to Non-PEO NEOs | (802,275) | 4,896,011 | 3,040,128 | (691,351) | 3,261,901 |

  133. Pay Versus Performance Table

    5.Total shareholder return represents that of the Company, assuming $100 was invested on December 31, 2020. 6.Peer group total shareholder return represents that of the S&P Composite 1500 Insurance Brokers Index, assuming $100 was invested on December 31, 2020. 7.Organic revenue is calculated as commissions and fees for the relevant period, excluding (i) the first twelve months of commissions and fees generated from new partners and (ii) commissions and fees from divestitures. Organic revenue growth is the change in organic revenue period-to-period, with prior period results adjusted to (i) include commissions and fees that were excluded from organic revenue in the prior period because the relevant partners had not yet reached the twelve-month owned mark, but which have reached the twelve-month owned mark in the current period, and (ii) exclude commissions and fees related to divestitures from organic revenue. Refer to the Appendix to this Proxy Statement for reconciliations of non-GAAP financial measures to comparable GAAP financial measures.

  134. Pay Versus Performance Table

    | | 2026 Proxy Statement | 61 |

  135. Pay Versus Performance Table

    | PAY VERSUS PERFORMANCE | TABLE OF CONTENTS |

  136. Pay Versus Performance Graphs

    Pay Versus Performance Graphs The following graphs display the relationships for compensation actually paid to PEO (“PEO CAP”) and average compensation actually paid to non-PEO NEOs (“NEO CAP”) versus TSR, net income (loss) and organic revenue growth for the five years ended December 31, 2025.

  137. Pay Versus Performance Graphs

    | COMPENSATION ACTUALLY PAID, BALDWIN TSR AND PEER GROUP TSR |

  138. Pay Versus Performance Graphs

    | COMPENSATION ACTUALLY PAID AND NET INCOME (LOSS) |

  139. Pay Versus Performance Graphs

    | 62 | 2026 Proxy Statement | |

  140. Pay Versus Performance Graphs

    | TABLE OF CONTENTS | PAY VERSUS PERFORMANCE |

  141. Pay Versus Performance Graphs

    | COMPENSATION ACTUALLY PAID AND ORGANIC REVENUE GROWTH |

  142. CEO Pay Ratio

    CEO Pay Ratio As required by Section 953(b) of the Dodd-Frank Wall Street Reform and Consumer Protection Act, and Item 402(u) of Regulation S-K, we are providing the ratio of the annual total compensation of Trevor Baldwin, our Chief Executive Officer (“CEO”), to the annual total compensation of the median compensated colleague (excluding Mr. Baldwin). For 2025, Mr. Baldwin’s total compensation was $5,253,032, as reported for 2025 in the “Total” column in the Summary Compensation Table, and the annual total compensation of our median compensated colleague was $82,962. The ratio between these two amounts was 63 to 1. This pay ratio is a reasonable estimate calculated in a manner consistent with Item 402(u) and the methodology described below. Because the SEC rules for identifying the median compensated colleague and calculating the pay ratio based on that colleague’s annual total compensation allow companies to adopt a variety of methodologies, to apply certain exclusions, and to make reasonable estimates and assumptions that reflect their compensation practices, the pay ratio reported by other companies may not be comparable to the pay ratio reported above, as other companies may have different employment and compensation practices and may utilize different methodologies, exclusions, estimates and assumptions in calculating their own pay ratios. As of December 31, 2025, our total colleague population consisted of approximately 4,200 individuals, and we used 2025 gross taxable income as set forth in our payroll data from these individuals to determine our median colleague on December 31, 2025. We calculated the annual total compensation of our median colleague for 2025 in accordance with the requirements of Item 402(c)(2)(x) of Regulation S-K, which is consistent with the methodology used to calculate the annual total compensation of our CEO, as reported for 2025 in the “Total” column of the Summary Compensation Table.

  143. CEO Pay Ratio

    | 64 | 2026 Proxy Statement | |