DEF 14A of Ryan Specialty Holdings, Inc., Mar 17, 2026

DEF 14A of Ryan Specialty Holdings, Inc.

Filed Mar 17, 2026 · FY20250001849253-26-000013

Open on EDGAR

  1. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    PROPOSAL NO. 1: ELECTION OF DIRECTORS The Board has nominated David P. Bolger, Michael G. Bungert, Francesca Cornelli, Nicholas D. Cortezi, and Anthony J. Kuczinski for election at the Annual Meeting to serve until the 2027 annual meeting of stockholders and until their successors are duly elected and qualified. Each of the nominees, other than Mr. Bungert, who was appointed to the Board in September 2025 to fill a vacancy upon the death of a director, has been previously elected by our stockholders. Mr. Bungert was initially recommended to the Compensation and Governance Committee by our Executive Chairman, Patrick G. Ryan. Dr. Cornelli and Messrs. Bolger, Bungert, Cortezi, and Kuczinski have each consented to be named in this Proxy Statement and indicated their willingness to serve if elected. Nomination of Directors The Compensation and Governance Committee of our Board identifies, evaluates, and recommends to the Board potential nominees for election to the Board. In reviewing potential nominees, the Compensation and Governance Committee considers the qualifications of each potential nominee with the qualification standards set forth in its committee charter and in our Corporate Governance Guidelines. Specifically, the Compensation and Governance Committee considers, among other things, (i) each potential nominee’s past attendance and performance at Board meetings and committee meetings, if applicable, (ii) the nominee’s ability to represent all stockholders without a conflict of interest, (iii) the nominee’s ability to work in and promote a productive environment, (iv) whether the nominee has sufficient time and willingness to fulfill the substantial duties and responsibilities of a director, (v) whether the nominee has demonstrated the high level of character, ethics, and integrity expected by the Company, (vi) whether the nominee possesses the broad professional and leadership experience and skills necessary to effectively respond to the complex issues encountered by a publicly-traded company, (vii) the nominee’s ability to apply sound and independent business judgment, and (viii) the viewpoint and background of the nominee. The Board membership criteria are set forth in our Corporate Governance Guidelines and Compensation and Governance Committee charter, copies of which are available under the tabs “Investors > Governance > Governance Documents” on our website at www.ryanspecialty.com. After reviewing the qualifications of potential Board candidates, the Compensation and Governance Committee presents its recommendations to the Board, which selects the final director nominees. The Company did not pay any fees to any third parties to identify or assist in identifying or evaluating nominees for the Annual Meeting. The Compensation and Governance Committee considers stockholder nominees using the same criteria set forth above. Stockholders who wish to present a potential nominee to the Compensation and Governance Committee for consideration for election at a future annual meeting of stockholders must provide the Compensation and Governance Committee with notice of the nomination and certain information regarding the candidate as described in our Bylaws and within the time periods set forth under the caption “Proposals of Stockholders and Communications with our Board.” Pursuant to our Corporate Governance Guidelines, the Company endeavors to have a Board consisting of directors who possess the highest personal and professional ethics, integrity and values and who are committed to representing the long- term interests of the Company and its stockholders. Nominees and Incumbent Directors The Compensation and Governance Committee has recommended, and the Board has nominated, Dr. Cornelli and Messrs. Bolger, Bungert, Cortezi, and Kuczinski for election as directors at the Annual Meeting to serve until the 2027 annual meeting of stockholders and until their successors are duly elected and qualified. Director Nominees

  2. MICHELLE L. COLLINS

    MICHELLE L. COLLINS Michelle L. Collins has served on our Board since our IPO in July 2021 and is a member of the Audit Committee. Since 2007, she has served as the president of Cambium LLC, a consulting firm. Ms. Collins was co-founder of Svoboda Capital Partners, LLC and served as Managing Director from 1998 to 2006. Prior to that, Ms. Collins was a principal in the Corporate Finance Department at William Blair & Company, LLC. Since 2014, Ms. Collins has served on the board of Ulta Beauty, Inc. She has also served on the boards of Canadian Imperial Bank of Commerce (“CIBC”) and CIBC Bancorp USA/CIBC Bank U.S. since 2017. Previously, she was a member of the mutual fund boards of Columbia Acorn and Wanger Advisors Trusts and the boards of directors of the following public and private companies: PrivateBankcorp, Inc., Integrys Energy Group, Inc., Molex, Inc., Bucyrus International, CDW Corporation, Coldwater Creek, Inc., McWhorter Technologies, Inc., and Health Care Service Corporation, a mutual reserve company. She earned a Bachelor of Arts from Yale University and a Master of Business Administration from Harvard Business School. We believe Ms. Collins is qualified to serve on our Board due to her extensive finance industry experience and experience as a director on the boards of other for-profit companies. JOHN W. ROGERS, JR. John W. Rogers, Jr., has served on our Board since 2014, has been our Lead Director since July 2025, and is a member of both the Compensation and Governance Committee and the Executive Committee. He is the Founder, Chairman, Co-CEO (since 2019; from 1983-2019 he served as Chief Executive Officer), and Chief Investment Officer of Ariel Investments. Mr. Rogers is a member of the mutual fund board of Ariel Investments Trust, serves as vice chair of the board of trustees of the University of Chicago, and as a member of the boards of directors of NIKE, Inc. and The New York Times Company. From 2000 to 2019, he served on the board of directors of Exelon Corp. and from 2003 to 2023 he served on the board of directors of McDonalds Corporation. Following the election of President Barack Obama, Mr. Rogers served as co-chair for the Presidential Inaugural Committee 2009, and in 2016 he joined the Barack Obama Foundation’s board of directors. He earned his Bachelor of Arts from Princeton University and in 2008 was awarded Princeton University's highest honor, the Woodrow Wilson Award, presented each year to the alumnus or alumna whose career embodies a commitment to national service. We believe Mr. Rogers is qualified to serve on our Board due to his extensive finance industry experience and experience as a director on the boards of other for-profit companies. Class I Directors: Continuing in Office Until 2028

  3. TIMOTHY W. TURNER

    TIMOTHY W. TURNER Timothy W. Turner became our Chief Executive Officer on October 1, 2024. Prior to that, he served as our President from March 2021 until October 1, 2024 and as the Chairman and CEO of RT Specialty from RT’s founding in 2010 until October 1, 2024. Mr. Turner has been a member of our Board of Directors since 2012 and is a member of the Executive Committee. Prior to co-founding RT Specialty, Mr. Turner was with CRC Insurance Services, Inc. (“CRC”) for 10 years and was President of CRC at the time of his departure. Prior to CRC, Mr. Turner worked for the Crump Group and was named President of its Chicago Office. Mr. Turner began his insurance career as a casualty broker with A.J. Renner & Associates in 1987. He has received a number of awards, and in 2020, one of the insurance industry’s most respected media outlets, the Insurance Insider, named Mr. Turner the Distribution Leader of the Year, honoring him as the year's most influential and outstanding individual in insurance distribution. In 2019, Mr. Turner received the prestigious Insurance Industry "Good Scout" Award from the Boy Scouts of America, Greater New York Councils. Additionally, Mr. Turner received the 2021 Spirit of Life Award from the City of Hope, National Insurance Industry Counsel. Before joining the insurance industry, Mr. Turner graduated from the Detroit Police Academy, served on the Wayne County SWAT Team, and was an undercover narcotics officer with the Narcotics Cocaine Task Force with the Michigan State Police. Mr. Turner earned a Bachelor of Science in Criminal Justice from Madonna University. We believe that Mr. Turner’s extensive and industry-leading experience in the area of insurance and his insight into our business as our President and the Chairman and CEO of RT Specialty qualifies him to serve on our Board.

  4. TIMOTHY W. TURNER

    | | 2026 Proxy Statement 20 |

  5. HENRY S. BIENEN, PH.D

    HENRY S. BIENEN, PH.D Henry S. Bienen has served on our Board since 2012, is the Chairperson of the Compensation and Governance Committee, and is a member of the Audit Committee. Dr. Bienen served as Northwestern University’s president from 1995 through 2009 and currently serves as president emeritus and interim president of Northwestern University. He was the James S. McDonnell Distinguished University Professor and Dean of the Woodrow Wilson School of Public and International Affairs at Princeton University prior to his appointment at Northwestern. Dr. Bienen is Emeritus Trustee of the Chicago Council on Global Affairs. Additionally, Dr. Bienen is on the boards of directors of Hedge Fund Guided Portfolio Solutions and Grosvenor Multi Strategy Funds, chairs the Advisory Committee of The Vistria Group’s Education Investments, and is a lifetime member of the board of MetroSquash, an urban squash and education program in Chicago. Furthermore, Dr. Bienen is a member of the board of the Lucas Museum of Narrative Art, was the chairman of the board of the Crown Center on Middle East Studies at Brandeis University, and was both a member and a past chairman of the board, and was both a member and a past chairman of the board of directors for Rasmussen University. Dr. Bienen is also a consultant for Academic Partnerships, an online project manager for regional public universities. Dr. Bienen served on the board of the Council on Foreign Relations from 2001 to 2011 and Bear Stearns Companies, Inc. from 2004 to 2008. He earned a Bachelor of Arts from Cornell University with honors, as well as a Master of Political Science and a PhD in Political Science from the University of Chicago. We believe Dr. Bienen is qualified to serve on our Board due to his extensive experience as a director on the boards of other for-profit companies.

  6. MICHAEL D. O’HALLERAN

    MICHAEL D. O’HALLERAN Michael D. O’Halleran has served on our Board since 2018. Mr. O’Halleran has been Executive Chairman of Geneva Re Ltd. since 2019 and previously served as a senior advisor at Ryan Specialty. Mr. O’Halleran was the founder, and for twenty-four years served as Executive Chairman, of Aon Re, a reinsurance brokerage and capital advisory firm. Additionally, Mr. O’Halleran was previously President and COO of Aon Corporation from 1999 to 2005. He also served on the following boards of directors: NuVasive, Inc., CareFusion, Inc., Cardinal Health, Inc., and Allegiance Corp. Mr. O’Halleran earned his Bachelor of Science from the University of Wisconsin - Whitewater. We believe Mr. O’Halleran is qualified to serve on our Board due to his extensive insurance industry experience. PATRICK G. RYAN, JR. Patrick G. Ryan, Jr., has served on our Board since January 2024 and is a technology entrepreneur and investor. He is the Founder and CEO of Incisent Labs Group, a holding company and incubator for creating new technology companies. Mr. Ryan also founded two high growth software as a service (SaaS) companies, each of which was ranked by Inc. Magazine as one of the four fastest growing software companies in the United States and cofounded venture capital firm Chicago Ventures. Mr. Ryan served on the board of directors of Penske Corporation, a $50 billion diversified transportation services company, for 25 years. He is a Trustee of Northwestern University and serves on its executive committee. He earned a Bachelor of Arts from Georgetown University and a Master of Business Administration from Northwestern University’s Kellogg School, as well as a Juris Doctorate cum laude from Northwestern School of Law. We believe Mr. Ryan is qualified to serve on our Board due to his experience as a founder of two successful technology companies and his financial experience as a CEO.

  7. MICHAEL D. O’HALLERAN

    | | 2026 Proxy Statement 21 |

  8. MICHAEL D. O’HALLERAN

    Vote Required Each of the five nominees who receive more “FOR” votes than “AGAINST” votes at the virtual Annual Meeting by stockholders entitled to vote thereon will be elected as a director to hold office until the 2027 annual meeting of stockholders and until their successors are elected and qualified, unless they resign, or their seats become vacant due to removal or death. Abstentions and broker non-votes will not affect the election of directors. Holders of proxies solicited by this Proxy Statement will vote the proxies received by them as directed on the Proxy Card or, if no direction is given, then FOR the election of each of the nominees named in this Proxy Statement.

  9. MICHAEL D. O’HALLERAN

    | | The Board recommends a vote “FOR” each of the five director nominees identified above. |

  10. MICHAEL D. O’HALLERAN

    | | 2026 Proxy Statement 22 |

  11. DIRECTOR COMPENSATION

    DIRECTOR COMPENSATION The following table presents the total compensation for each person who served as a non-employee director on our Board during 2025. Other than as set forth in the table and described more fully below, we did not pay any compensation, make any equity or non-equity awards, or pay any other compensation to any of the non-employee directors on the Board. Patrick G. Ryan and Timothy W. Turner, each of whom are employed by the Company, did not receive any additional compensation for their service on the Board. Robert M. Le Blanc, who retired from the Board effective February 11, 2026, agreed to forgo any cash or equity compensation for his service on the Board. Michael D. O’Halleran is eligible to receive the annual equity grant in accordance with the Company’s Non-Employee Director Compensation Policy, discussed below, but does not receive any additional cash payments for his service to the Board in light of his role as Executive Chairman of Geneva Re.

  12. DIRECTOR COMPENSATION

    | Name | Fees Earned or Paid in Cash ($) | Stock Awards ($)(1) | Total ($) | | Henry S. Bienen (2) | 131,481 | 162,500 | 293,981 | | David P. Bolger | 155,000 | 162,500 | 317,500 | | Michael G. Bungert (3) | 36,196 | — | 36,196 | | Michelle L. Collins | 120,000 | 162,500 | 282,500 | | Francesca Cornelli | 120,000 | 162,500 | 282,500 | | Nicholas D. Cortezi | 120,000 | 162,500 | 282,500 | | D. Cameron Findlay (4) | 95,380 | 162,500 | 257,880 | | Anthony J. Kuczinski | 120,000 | 162,500 | 282,500 | | Robert M. Le Blanc | — | — | — | | Michael D. O’Halleran | — | 162,500 | 162,500 | | John W. Rogers, Jr. (5) | 136,073 | 162,500 | 298,573 | | Patrick G. Ryan, Jr. | 120,000 | 162,500 | 282,500 |

  13. DIRECTOR COMPENSATION

    (1)On May 30, 2025, each of the non-employee directors, other than Mr. Bungert who was not elected to the Board until September 2025, received a grant of 2,323 Restricted Stock Units (“RSUs”), rounded down to the nearest whole share, with a grant date fair value of approximately $162,500, as compensation for their full year of service to the Company ending at the 2025 annual meeting of stockholders. RSUs were fully vested as of the grant date and each RSU represents a right to receive one fully vested share of Class A common stock within 30 days of grant (or, if elected by the director, upon the earlier of the director’s “separation from service” or a “change in control,” each as defined in the applicable award agreement). (2)Henry S. Bienen was appointed as chair of the Compensation and Governance Committee on July 16, 2025, and received a prorated fee for his services as chair of the Compensation and Governance Committee for the third quarter of 2025. (3)Michael G. Bungert began his services to the Board on September 12, 2025, and received a prorated fee for his services to the Board for the third quarter of 2025. (4)D. Cameron Findlay passed away on July 11, 2025, and received a prorated fee for his services to the Board as both a director and the Lead Director for the third quarter of 2025. (5)John W. Rogers, Jr., was appointed Lead Director on July 16, 2025, and received a prorated fee for his services as Lead Director for the third quarter of 2025. In October 2024, after a detailed review of director compensation provided by our peers, the Board amended the Non- Employee Director Compensation Policy to provide its non-employee members the following compensation to be effective January 1, 2025: (i) an annual cash retainer of $120,000, (ii) an annual grant of equity with a grant date fair value of $200,000, (iii) an annual fee for the Chair of the Audit Committee of $35,000, (iv) an annual fee for the Chair of the Compensation and Governance Committee of $25,000, and (v) an annual fee for the Lead Director of the Board of $35,000. Other than the chairperson of the respective Board committees, no participating committee members receive additional compensation for their participation on such committees. Mr. O’Halleran will continue to forgo any cash compensation as a director and Mr. Le Blanc agreed to forgo any cash or equity compensation for his service as a director. The annual cash retainer, as well as the Lead Director fee and committee chairperson fee, are all paid quarterly. Our Non-Employee Director Compensation Policy provides that each of our non-employee directors will receive an annual grant of equity. With the exception of Mr. Le Blanc, who elected not to receive any compensation for his service on the Board, we make an annual equity grant to our non-employee directors each year on the date of the Company’s annual meeting of stockholders. The grants are compensation for a year of service comprising the third and fourth quarters of the prior year and the first and second quarters of the current year. Should any director not serve for the full year covered by the

  14. DIRECTOR COMPENSATION

    | | 2026 Proxy Statement 23 |

  15. DIRECTOR COMPENSATION

    grant (from annual meeting to annual meeting), the grant will be prorated. Each director that served for the entire year through the 2025 annual meeting of stockholders received a grant of equity on May 30, 2025 in the form of RSUs with a grant date fair value equal to approximately $162,500, rounded down to the nearest whole share (which reflects two quarters prorated at $125,000 and two quarters prorated at $200,000). The RSUs were fully vested as of the grant date and each represents a right to receive one fully vested share of Class A common stock within 30 days of the grant date (or, at the election of the director, upon the earlier of the director’s “separation from service” or a “change in control,” each as defined in the applicable award agreement). In October 2025, after a detailed review of director compensation provided by our peers, the Board did not make any changes to the Non-Employee Director Compensation Policy. Stock Ownership Guidelines The Company has stock ownership guidelines which apply to the Company’s non-employee directors. Pursuant to the guidelines, the Company’s non-employee directors are expected to accumulate Company common stock or equivalents with a value equivalent to five times their annual cash retainer, within five years of the adoption of the requirement or within five years of a director joining the Board. If a non-employee director does not hold sufficient shares of the Company’s common stock or equivalents to meet the guideline requirements, they will then be required to hold 100% of their current Company common stock or equivalents plus any future grants until they have met the requirement. Compliance with the stock ownership requirements is measured annually and calculated on the last trading day of each calendar year, based on the closing price of the Company’s stock on such trading day. The guidelines were adopted on April 21, 2021, such that each non-employee director serving at that time has until April 21, 2026 to meet the guidelines. The table below sets forth the date by which each of our current non-employee directors is required to meet the guidelines.

  16. DIRECTOR COMPENSATION

    | Director Name | Date Compliance is Required | | Henry S. Bienen | April 21, 2026 | | David P. Bolger | April 21, 2026 | | Michael G. Bungert | September 12, 2030 | | Michelle L. Collins | July 21, 2026 | | Francesca Cornelli | July 31, 2028 | | Nicholas D. Cortezi | June 1, 2028 | | Anthony J. Kuczinski | October 30, 2028 | | Michael D. O’Halleran | April 21, 2026 | | John W. Rogers, Jr. | April 21, 2026 | | Patrick G. Ryan, Jr. | January 1, 2029 |

  17. DIRECTOR COMPENSATION

    Each non-employee director has achieved holdings in excess of the applicable requirement as of December 31, 2025, or is within the five-year compliance period.

  18. DIRECTOR COMPENSATION

    | | 2026 Proxy Statement 24 |

  19. COMPENSATION DISCUSSION AND ANALYSIS

    | ✓ | Annual “say-on-pay” vote (as recommended by the Board and management). | | ✓ | Independent compensation consultant selected, engaged, and overseen by the Compensation and Governance Committee. | | ✓ | A substantial majority of total compensation for executives tied to performance. | | ✓ | Clawback policy in place in case of an accounting restatement. | | ✓ | Compensation and Governance Committee oversight of risks associated with compensation policies and practices. | | ✓ | Long-term incentive program with long-term vesting schedules. | | ✓ | Stock ownership guidelines to align interests of executives with our stockholders. | | ✓ | Majority of executive compensation delivered in the form of long-term incentives. | | ✓ | Compensation and Governance Committee consists only of independent Board members. |

  20. COMPENSATION DISCUSSION AND ANALYSIS

    | No backdating of share options and no option repricing without stockholder approval.x | | No excise tax gross-ups.x | | No guaranteed annual incentive payouts without regard to performance.x | | No pledging (absent Board approval) or hedging of Company stock by directors, executive officers, or employees.x |

  21. COMPENSATION DISCUSSION AND ANALYSIS

    | Objective | How we accomplish this objective | | Alignment with Stockholders | •Annual short-term cash incentive program tied to key business objectives, which objectives lead to long-term stockholder value creation •Long-term incentives vest over multiple years and reward sustained stockholder value creation •IPO awards are subject to lock-up provisions | | Attract and Retain | •Competitive compensation for executives is based upon job responsibilities, experience, individual performance, and comparisons to the market | | Pay for Performance | •Majority of executive compensation is delivered in the form of variable, at-risk compensation •Annual incentive plan payouts are determined based on financial performance •The Compensation and Governance Committee establishes rigorous targets for the annual incentive plan •Long-term incentives are delivered in the form of performance-based awards, stock options or restricted equity grants, which reward participants for increasing the stock price and directly align executives to the stockholder experience | | Sound Risk Management | •Conduct an annual risk assessment of our executive compensation programs •Compensation and Governance Committee is made up of independent directors and retains an independent compensation consultant •Incorporate a variety of corporate governance and compensation best practices |

  22. Base Salary

    The Compensation and Governance Committee reviewed each NEO’s base salary in January 2026. They considered the new positions and responsibilities of certain of our NEOs and compared their current compensation with our peer group. Based on our philosophy of targeting base salary at or above the 75th percentile when compared to the members of our peer group, the Compensation and Governance Committee approved the following compensation changes to be effective in March 2026: Ms. Hamilton - $750,000 and Mr. Keogh - $725,000. The base salaries for Messrs. Ryan, Turner, and Wuller were not increased (or otherwise adjusted) from 2025 to 2026.

  23. Short-Term Incentive Compensation

    Short-Term Incentive Compensation STI awards are an integral component of our NEOs’ total compensation and are based on our financial results and individual performance. They are intended to deliver exceptional pay for exceptional performance and provide a well-timed link between recent performance and individual compensation. Each NEO is eligible to receive an annual STI award expressed as a percentage of their base salary. STI targets for the Company’s executive officers were established by the Compensation and Governance Committee in early 2025 following a thorough evaluation of our executive officers’ total compensation and market practices.

  24. Short-Term Incentive Compensation

    | Named Executive Officer | 2025 Bonus Target % | | Patrick G. Ryan | 200% | | Timothy W. Turner | 200% | | Janice M. Hamilton | 200% | | Stephen P. Keogh | 150% | | Benjamin M. Wuller | 200% | | Jeremiah R. Bickham | 200% |

  25. The 2025 Executive Incentive Corporate Plan

    | Metric | Percent of Bonus | | Organic Revenue Growth Rate | 35% | | Adjusted EBITDAC Margin | 35% | | Individual Merit-Based Achievement | 30% |

  26. The 2025 Executive Incentive Corporate Plan

    | Organic Revenue Growth Rate | Target Payout % | | <10% | 0% | | 13 - 15% | 100% | | >18% | 150% |

  27. The 2025 Executive Incentive Corporate Plan

    | Adjusted EBITDAC Margin | Target Payout % | | <33.25% | 0% | | 33.50 - 33.70% | 100% | | >34.20% | 150% |

  28. The 2025 Executive Incentive Corporate Plan

    Target payout percentage for Adjusted EBITDAC Margin between the benchmarks set forth above was determined based on a graduated basis. Adjusted EBITDAC Margin is calculated by taking our Adjusted EBITDAC as a percentage of our Total revenue. Adjusted EBITDAC, for the purposes of Short-Term Incentive Compensation, is calculated by taking our Net income before Interest expense, net, Income tax expense, Depreciation, Amortization, and Change in contingent consideration, adjusted to reflect items such as (i) equity-based compensation, (ii) acquisition and restructuring related expenses, (iii) exclusion of the results of unplanned M&A completed in 2025 as the targets were set prior to the M&A being completed, (iv) exclusion of the impact of any higher (or lower) than target discretionary incentive accruals, and (v) other exceptional or non-recurring items, as applicable. Please see “Management’s Discussion and Analysis of Financial Condition and Results of Operations - Non-GAAP Financial Measures and Key Performance Indicators - Adjusted EBITDAC Margin” in our Annual Report on Form 10-K for the year ended December 31, 2025, for additional information about our method of calculation for Adjusted EBITDAC Margin. Individual Merit-Based achievement is linked to an individual’s contribution towards (i) culture, (ii) results, (iii) client centricity, (iv) teamwork, and (v) inclusion.

  29. The 2025 Executive Incentive Business Unit Plan

    | Metric | Percent of Bonus | | Organic Revenue Growth Rate | 15% | | Adjusted EBITDAC Margin | 15% | | Business Unit Organic Revenue Growth Rate | 20% | | Business Unit Adjusted Expense Margin | 20% | | Individual Merit-Based Achievement | 30% |

  30. The 2025 Executive Incentive Business Unit Plan

    | Business Unit Revenue Growth Rate | Target Payout % | | <5% | 0% | | 10 - 12% | 100% | | >16% | 150% |

  31. The 2025 Executive Incentive Business Unit Plan

    | Business Unit Adjusted Expense Margin | Target Payout % | | >51.89% | 0% | | 50.07 - 50.57% | 100% | | <49.07% | 150% |

  32. 2025 Bonus Determination

    2025 Bonus Determination Organic Revenue Growth Rate for 2025 was 10.1%, resulting in an STI award of 3.3% of target for both plans. Adjusted EBITDAC Margin, based on compensation amounts accrued throughout the year at target, was 30.97%, resulting in an STI award of 0% of target for both plans. The Business Unit Organic Revenue Growth Rate for 2025 was 9.30%, resulting in an STI award of 86.0% of target. The Business Unit Adjusted Expense Margin was 54.80%, resulting in an STI award of 0% of target. The Compensation and Governance Committee, in reviewing the Merit-Based Achievement component of each NEO’s STI award, relied on input from Messrs. Ryan and Turner for each NEO other than Messrs. Ryan and Turner. For each of the NEOs other than Messrs. Ryan and Turner, the Compensation and Governance Committee determined that based on each NEO’s contribution to the Company’s achievement, the Individual Merit-Based Achievement component of each such NEO’s STI award for 2025 would be 100% of target, with the primary contributing factor of such determination being the individual contributions that each NEO provided to the Company’s successes in 2025. As a result, the total STI award for each of our NEOs on our Executive Incentive Corporate Plan for 2025 was approximately 31.2% of target and the total STI award for Mr. Wuller, who is on the Executive Incentive Business Unit Plan, was approximately 47.7% of target. The Compensation and Governance Committee, after due consideration and input from Messrs. Ryan and Turner that their bonuses would be better used to provide additional funds to increase bonuses for the Company’s bonus-eligible non- executive employees who delivered exceptional performance, accepted Messrs. Ryan’s and Turner’s voluntary proposal to forgo 2025 STI and, exercising its negative discretion, awarded each of Messrs. Ryan and Turner 0% of target. The following table sets forth the STI award payments earned by each of our NEOs in 2025.

  33. 2025 Bonus Determination

    | Named Executive Officer | 2025 Bonus Payment | | Patrick G. Ryan | $— | | Timothy W. Turner | — | | Janice M. Hamilton | 374,000 | | Stephen P. Keogh(1) | 187,000 | | Benjamin M. Wuller | 810,900 | | Jeremiah R. Bickham(2) | 407,899 |

  34. 2025 Bonus Determination

    (1) Stephen P. Keogh began his employment on May 1, 2025, and his bonus amount has been prorated for the year based on the number of days employed. (2)Jeremiah R. Bickham separated from the Company on October 8, 2025, and his bonus amount has been prorated for the year based on the number of days employed.

  35. 2025 Bonus Determination

    | | 2026 Proxy Statement 35 |

  36. 2026 STI Compensation Plans and Bonus Target Percentages

    2026 STI Compensation Plans and Bonus Target Percentages The target bonus percentages for all NEOs remain the same in 2026 as they were in 2025. For all NEOs, other than Mr. Wuller, STI compensation for 2026 will be determined based on the Company achieving predetermined metrics for Organic Revenue Growth Rate and Adjusted EBITDAC Margin, as well as the Individual Merit-Based Achievement component as determined by the Compensation and Governance Committee. Mr. Wuller’s STI compensation for 2026 will be determined based on the Company achieving predetermined metrics for Organic Revenue Growth Rate, Adjusted EBITDAC Margin, Business Unit Organic Revenue Growth Rate, and Business Unit Adjusted Expense Margin, as well as the Individual Merit- Based Achievement component as determined by the Compensation and Governance Committee.

  37. Long-Term Incentive Compensation

    Long-Term Incentive Compensation All equity holdings in Ryan Specialty, LLC were converted to equity in a new holding company, New Ryan Specialty, LLC (“New LLC”), that was formed as a Delaware limited liability company on April 20, 2021, for the purpose of becoming an intermediate holding company between Ryan Specialty Holdings, Inc., and Ryan Specialty, LLC. On September 30, 2021, the equity interest holders of Ryan Specialty, LLC exchanged equity interests in Ryan Specialty, LLC for LLC Common Units (as defined below) in New LLC. All new incentive equity relating to LLC Common Units granted after September 30, 2021, will be issued in New LLC. As Ryan Specialty, LLC is substantively the same as New LLC, as previously noted, for the purpose of this document we will refer to both New LLC and Ryan Specialty, LLC as the “LLC”. Our publicly traded stock differentiates Ryan Specialty from most of our competition by providing us with a unique currency to attract and retain talent. We believe that our executive officers, including our NEOs, should have a significant equity stake in the Company to incentivize performance, align their interest with one another and our stockholders, and facilitate retention. Many of our executive officers held significant equity in the Company prior to our IPO. Due to the change in our structure made in connection with the IPO, all vested and unvested incentive equity outstanding prior to the IPO was exchanged for new units at the IPO as described herein. The equity received in exchange for existing equity was on substantially the same terms and conditions (including vesting terms) as the pre-IPO equity. We further used the IPO as an opportunity to provide significant new “staking grants” to some of our executive officers in order to bring them on par with their similarly situated colleagues. The staking grants vest over five or ten year periods, depending on the nature of the grant and the particular circumstances of each recipient. As the current equity grants vest over time, we will need to consider ad hoc grants and an annual grant program for executive officers in order to maintain our objectives. The outstanding LTI awards currently held by our NEOs consist of (i) LLC Common Units (as defined below), (ii) Class C Units (as defined below), (iii) RLUs (as defined below), and (iv) PLUs and PSUs (each, as defined below).

  38. Common Units

    Common Units Prior to our IPO, some of our NEOs held awards of common units pursuant to the Limited Liability Company Agreement of Ryan Specialty, LLC (the “Original Units”). The Original Units were profits interests that represented actual voting equity interests meant to enable certain employees to share in our financial success after our preferred unitholders received a certain level of return on their investment. The Original Units entitled unitholders to a percentage of future distributions, but only after all preferred unitholders had received cumulative cash distributions of a certain multiple return and only to the extent that distributions exceeded the return threshold associated with such Original Units. The Original Units were subject to time-based vesting and generally vested in five equal annual installments beginning on the first anniversary of the date of grant, subject to the NEO’s continued employment with us through each vesting date. In connection with the IPO, the Original Units were converted into non-voting common units in the LLC (“LLC Common Units”), subject to the same vesting and forfeiture provisions as the Original Units. Vested LLC Common Units are exchangeable into Class A common stock at the election of the holder, provided that the Company may elect (determined by a majority of the Company’s disinterested directors) to deliver cash in lieu of stock only to the extent that the Company has received cash proceeds pursuant to a secondary offering. Each holder of LLC Common Units also holds one share of Class B common stock for each LLC Common Unit they hold.

  39. Class C Common Incentive Units

    Class C Common Incentive Units Certain of our NEOs hold Class C Common Incentive Units in the LLC (“Class C Units”), which are profits interests that entitle the holder to a percentage of future distributions of the LLC, but only after a specified return threshold is met. Certain of these Class C Units were granted in connection with the conversion of the Original Units into LLC Common Units (such Class C Units, the “Reload Class C Units”) and were intended to ameliorate the recipients’ otherwise reduced percentage of future value accretion following the conversion of their “appreciation only” Original Units into a smaller number of “full value” LLC Common Units. The Reload Class C Units are subject to time-based vesting, and vest either 1/3 on each of the third, fourth, and fifth anniversaries of the IPO or 100% on the third anniversary of the IPO, in each case subject to the NEO’s continued employment through each vesting date (other than for those exceptions provided in the award agreement).

  40. Class C Common Incentive Units

    Other Class C Units were granted as new awards to certain NEOs in connection with the IPO (the “Staking Class C Units”) and are intended to reward future performance. The Staking Class C Units are subject to time vesting and vest 10% on each of the third through ninth anniversaries of the IPO, with the final 30% vesting on the tenth anniversary of the IPO, in each case, subject to the NEO’s continued employment through each vesting date (other than for those exceptions provided in the award agreement). In 2023, we granted a new award to Mr. Wuller (the “2023 Class C Units”) and such award is intended to reward future performance. The 2023 Class C Units are subject to time vesting and vest 20% on April 1, 2026, 2027, 2028, 2029 and 2030 in each case, subject to continued employment through each vesting date (other than for those exceptions provided in the award agreement). Vested Class C Units (Reload Class C Units, Staking Class C Units and 2023 Class C Units) are exchangeable into a number of shares of Class A common stock of equivalent economic value at the election of the holder, provided that the Company may elect (as determined by a majority of the Company’s disinterested directors) to deliver cash in lieu of stock only to the extent that the Company has received cash proceeds pursuant to a secondary offering.

  41. Restricted LLC Units

    Restricted LLC Units Awards of Restricted LLC Units (“RLUs”) were granted as new awards to certain NEOs in connection with the IPO (the “Staking RLUs”) and are intended to reward future performance. The Staking RLUs are subject to time vesting and vest 10% on each of the third through ninth anniversaries of the IPO, with the final 30% vesting on the tenth anniversary of the IPO, in each case, subject to the NEO’s continued employment through each vesting date (other than for those exceptions provided in the award agreement). In 2022, each of the NEOs, other than Messrs. Ryan and Keogh, received a grant of RLUs (the “2022 RLUs”) in recognition of the exceptional performance achieved by the Company in 2021. Each 2022 RLU represents the right to receive one LLC Common Unit upon vesting of the RLU. The 2022 RLUs vested in equal installments on April 1, 2023, 2024 and 2025, in each case subject to the NEO’s continued employment through each vesting date (other than for those exceptions provided in the award agreement).

  42. Performance LLC Units and Performance Stock Units

    Performance LLC Units and Performance Stock Units In March 2024, each of the NEOs, other than Mr. Ryan, Ms. Hamilton, and Mr. Keogh, received a grant of long-term performance-based awards which vest either into LLC Common Units (“PLUs”) or shares of Class A common stock (“2024 PSUs”). Ms. Hamilton received a grant of 2024 PSUs on the same terms in November 2024, shortly after her promotion to CFO. These awards are intended to align the recipients’ compensation with Company performance and our key financial metrics, promoting leadership goal continuity and retention, and driving shareholder value. Each PLU or 2024 PSU represents the right to receive one LLC Common Unit or one share of Class A common stock upon vesting, respectively. The PLUs and 2024 PSUs vest on April 1, 2029 (the “Certification Date”) upon, and subject to, the attainment of certain performance-based targets and subject to the NEO’s continued employment through January 1, 2029 (other than for those exceptions provided in the award agreement). The performance-based metrics that must be met are as follows: (i) achievement of an Adjusted EBITDAC Margin Target by 2027 and maintained through 2028, (ii) achievement of a four-year Organic Revenue Growth Compound Annual Growth Rate (“CAGR”) target from 2024 through 2027, and (iii) stock price CAGR targets measured from the closing stock price on February 29, 2024 of the Class A common stock to the average of (a) the volume weighted average price (“VWAP”) of the Class A common stock for the fourth quarter of 2027 and (b) the VWAP of the Class A common stock for the first quarter of 2028. Both the Adjusted EBITDAC Margin and the Organic Revenue Growth CAGR targets must be met for the awards to vest. The stock price CAGR targets will determine how many LLC Common Units the PLUs vest into and how many shares of Class A common stock the 2024 PSUs vest into. If the Adjusted EBITDAC Margin and the Organic Revenue Growth CAGR targets have been met, then at the threshold stock price CAGR, the PLUs and 2024 PSUs will vest into 75% of the LLC Common Units or Class A common stock subject to the award; at the target stock price CAGR the PLUs and 2024 PSUs will vest into 100% of the LLC Common Units or Class A common stock subject to the award; and at the Maximum stock price CAGR, the PLUs and 2024 PSUs will vest into 150% of the LLC Common Units or Class A common stock subject to the award. If the actual stock price CAGR is below the threshold amount, the PLUs and 2024 PSUs will be forfeited. Payout percentage based on a stock price CAGR between the benchmarks discussed above will be determined based on a graduated basis. Mr. Keogh received a performance-based award in May 2025, shortly after he joined the Company (“2025 PSUs” and together with the 2024 PSUs, the “PSUs”). Similar to the 2024 PSUs, the 2025 PSUs are intended to align the recipient’s compensation with Company performance and certain of our key financial metrics, promoting leadership goal continuity and retention, and driving shareholder value. Each 2025 PSU represents the right to receive one share of Class A common stock upon vesting. The 2025 PSUs vest on April 1, 2030 (the “Vesting Date”) upon, and subject to, the attainment of certain performance-based targets and subject to the NEO’s continued employment through the Vesting Date (other than for those exceptions provided in the award agreement). The performance-based metrics that must be met are as follows: (i) achievement of a five-year Organic Revenue Growth CAGR target from 2025 through 2029 and (ii) stock price CAGR targets measured from the closing stock price on March 4, 2025 of the Class A common stock to the VWAP of the Class A common stock for the fourth quarter of 2029. The Organic Revenue Growth CAGR target must be met for the award to vest. The stock price CAGR targets will determine how many shares of Class A common stock the 2025 PSUs vest into. If the Organic Revenue Growth CAGR target has been met, then at the threshold stock price CAGR, the 2025 PSUs will vest into 75% of the Class A common stock subject to the award; at the target stock price CAGR, the 2025 PSUs will vest into 100%

  43. Performance LLC Units and Performance Stock Units

    | | 2026 Proxy Statement 37 |

  44. Performance LLC Units and Performance Stock Units

    of the Class A common stock subject to the award; and at the maximum stock price CAGR, the 2025 PSUs will vest into 150% of the Class A common stock subject to the award. If the actual stock price CAGR is below the threshold amount, the 2025 PSUs will be forfeited. Payout percentage based on a stock price CAGR between the benchmarks discussed above will be determined based on a graduated basis.

  45. Treatment of Long-Term Incentive Awards Upon a Termination of Employment

    Treatment of Long-Term Incentive Awards Upon a Termination of Employment For LTI awards issued in conjunction with the IPO (LLC Common Units, Staking Class C Units, Reload Class C Units and Staking RLUs), if an NEO’s employment is terminated (i) by us without “Cause,” (ii) due to the NEO’s death or disability, or (iii) the NEO retires in good standing (as determined by the Board) after reaching the age of 65 (a “Qualified Retirement”), and, in each case, subject to the NEO’s continued compliance with the restrictive covenants set forth in the applicable grant agreement, the unvested LLC Common Units, Reload Class C Units, and Staking Class C Units held by the NEO will continue to vest as if the NEO remained employed with us through each vesting date and the Staking RLUs will accelerate. Upon any other termination of employment, any unvested LLC Common Units, Staking Class C Units, Reload Class C Units, and Staking RLUs will be forfeited. For the RLUs granted post-IPO, the award agreements provide that (i) in the event an NEO’s employment with us is terminated by us without “Cause,” then the portion of RLUs eligible to vest on the next vesting date following the termination will immediately vest and (ii) in the event of an NEO's death or disability, vesting of all unvested RLUs will fully accelerate. The concept of a Qualified Retirement has been eliminated from the RLU grant agreements and upon any other termination of employment, the RLUs will be forfeited. For the 2023 Class C Units, the award agreements provide that (i) in the event the NEO's employment with us is terminated by us without “Cause,” then the portion of 2023 Class C Units eligible to vest on the next vesting date following the termination will continue to vest as if the NEO remained employed with us through such next vesting date and (ii) in the event of the NEO's death or disability, then all of the unvested 2023 Class C Units will continue to vest as if the NEO remained employed with us through each vesting date. The concept of a Qualified Retirement has been eliminated from the grant agreements for the 2023 Class C Units and upon any other termination of employment, any unvested 2023 Class C Units will be forfeited. For the PLUs or PSUs, the award agreements provide that (i) in the event an NEO’s employment with us is terminated by us without “Cause,” then the PLUs or PSUs will remain outstanding and eligible to vest on the Certification Date or Vesting Date in accordance with the performance-based metrics described above, but the number of PLUs or PSUs earned will be pro- rated based on the applicable date of termination and (ii) in the event of an NEO’s death or disability, a number of PLUs or PSUs equal to the actual number of PLUs or PSUs earned as of the date of termination will vest in accordance with the performance metrics described above generally based on actual performance (with the applicable performance period deemed to have ended as of the date of termination, and for the PLUs and 2024 PSUs, the Adjusted EBITDAC Margin Targets deemed achieved as of the date of termination). Policies and Practices Related to the Grant of Certain Equity Awards Close in Time to the Release of Material Nonpublic Information The Company grants awards of stock options and Class C Units, which are profits interests that entitle the holder to a percentage of future distributions of the LLC, but only after a specified return threshold is met. Even though the Class C Units do not require the payment of an exercise price, they are most similar economically to stock options and are generally categorized as an instrument with an “option-like feature.” While the Company does not have a written policy regarding its equity grants, it is the Company’s practice to make grants no more than once per quarter and for each quarterly grant of equity to be effective on the third business day following the announcement of earnings for that quarter or as soon thereafter as is reasonably practicable under the circumstances. Neither the Board nor the Compensation and Governance Committee seeks to time equity grants to take advantage of information, either positive or negative, about our Company that has not been publicly disclosed. During the year ended December 31, 2025, we did not award any stock options or Class C Units to our NEOs. Stock Ownership Guidelines The Board adopted stock ownership guidelines that apply to all of our executive officers. The guidelines require our Chief Executive Officer to accumulate Company stock with a value equivalent to six times their annual base salary and all other executive officers are required to accumulate Company stock with a value equivalent to four times their annual base salary, all within five years of the adoption of the requirement or within five years of being appointed as an executive officer of the Company. If an executive officer becomes subject to a greater stock ownership requirement due to promotion, such person is expected to meet the higher stock ownership requirement within 5 years after first becoming subject to the guidelines or within 3 years after first becoming subject to the greater stock ownership requirement, whichever is longer. If an executive

  46. Treatment of Long-Term Incentive Awards Upon a Termination of Employment

    | | 2026 Proxy Statement 38 |

  47. Treatment of Long-Term Incentive Awards Upon a Termination of Employment

    officer does not hold sufficient shares of the Company’s stock to meet the guideline requirements, they will then be required to hold 100% of their current Company stock plus any future grants until they have met the requirement. Compliance with the stock ownership requirements is measured annually and calculated on the last trading day of each calendar year, based on the closing price of the Company’s stock on such trading day. For purposes of determining compliance with stock ownership requirements, the following forms of equity interests in the Company, whether vested or unvested, are considered: •Class A common stock owned directly or beneficially by the individual or his or her immediate family members; •Restricted shares of Class A common stock, including shares granted but not vested; •Class A common stock issuable upon the net after-tax settlement of RSUs; •Class A common stock issuable upon the exercise of stock options; •LLC Common Units on an as converted basis with the shares of Class A common stock issuable upon the exchange of such LLC Common Units; •Class C Units on an as converted basis with the shares of Class A common stock issuable upon the exchange of such Class C Units; and •LLC Common Units issuable upon the net after-tax settlement of any RLUs on an as converted basis with the shares of Class A common stock issuable upon the exchange of such LLC Common Units. The guidelines were adopted on June 7, 2022, such that each executive officer serving at that time has until June 7, 2027, to meet the guidelines. For all other executive officers, the required compliance date is based on the date that such individual became an executive officer of the Company or received a promotion as an existing executive officer. Each of our executive officers’ respective compliance date is set forth in the table below:

  48. Treatment of Long-Term Incentive Awards Upon a Termination of Employment

    | Executive Officer | Stock Ownership Guidelines Compliance Date | | Patrick G. Ryan | June 7, 2027 | | Timothy W. Turner | October 1, 2027 | | Brendan M. Mulshine | June 7, 2027 | | Stephen P. Keogh | May 1, 2030 | | Janice M. Hamilton | October 1, 2029 | | Michael L. Conklin | August 14, 2028 | | Mark S. Katz | June 7, 2027 | | Benjamin M. Wuller | October 30, 2029 |

  49. Treatment of Long-Term Incentive Awards Upon a Termination of Employment

    Each of our executive officers has achieved holdings in excess of the applicable requirement as of December 31, 2025, or is within the five-year compliance period. Other Benefits for Named Executive Officers Employee Welfare Benefit Plans Our NEOs are eligible to participate in the medical, life insurance, and other welfare benefits available to all other colleagues. There are no special medical plans or other welfare plans for our NEOs. Retirement Benefits We have not maintained, and do not currently maintain, a defined benefit pension plan. We currently make available a retirement plan intended to provide benefits under Section 401(k) of the Internal Revenue Code, pursuant to which employees (including our NEOs) may elect to defer a portion of their compensation on a pre-tax or post-tax basis and have it contributed to the plan. Contributions are allocated to each participant’s individual account and are then invested in selected investment alternatives according to the participant’s directions. We have historically matched 50% of elective deferrals up to

  50. Treatment of Long-Term Incentive Awards Upon a Termination of Employment

    | | 2026 Proxy Statement 39 |

  51. Treatment of Long-Term Incentive Awards Upon a Termination of Employment

    a maximum per participant per calendar year. All employee contributions to our 401(k) plan are 100% vested at all times. Employer contributions vest over three years, such that all employer contributions to our 401(k) plan are fully vested for employees who remain employed by us for at least three years. All contributions under our 401(k) plan are subject to certain annual dollar limitations in accordance with applicable laws, which are periodically adjusted for changes in the cost of living. Matching employer contributions are not guaranteed for any year. We also sponsor the Ryan Specialty Nonqualified Deferred Compensation Plan (the “Nonqualified Deferred Compensation Plan”), which allows certain highly compensated employees to defer a portion of their base salary and STI bonus to a later date pursuant to an advance deferral election. As of December 31, 2025, none of our NEOs have participated in the Nonqualified Deferred Compensation Plan. Our LTI awards granted at the IPO provide for continued vesting on their original vesting schedule (or, in the case of RLUs granted in connection with the IPO, accelerated vesting) in the case of a Qualified Retirement. See “Long-Term Incentive Compensation — Treatment of Long-Term Incentive Upon a Termination of Employment” above for more information. Severance Plan The Compensation and Governance Committee believes that severance benefits are a necessary component of a competitive compensation program because they minimize distraction and ensure continuity during times of uncertainty or transition, including during a change in control. In certain circumstances, such benefits are consideration for an executive’s agreement not to compete. Set forth below is a summary of the termination arrangements we have with our NEOs. All NEOs are participants in the Executive Severance Plan (the “Severance Plan”) as further described below. Under the Severance Plan, the Company will provide different benefits depending on whether the severance to be provided relates to a qualifying termination within six months prior to, or 18 months following, a “Change in Control” (as defined in the Severance Plan) (a “Change-in-Control Termination”) or a termination outside of such time period (a “Non-Change-in-Control Termination”). For a qualifying termination, our NEOs will be entitled to the following benefits:

  52. Treatment of Long-Term Incentive Awards Upon a Termination of Employment

    | | Non-Change-in Control Termination | Change-in-Control Termination | | Qualifying Termination | Termination without cause or by employee for good reason | Termination without cause or by employee for good reason | | Cash Severance | Executive Chairman and CEO: 1.5 X Base Salary and Target Bonus All other NEOs: 1.0 X Base Salary and Target Bonus | All NEOs: 2.0 X Base Salary and Target Bonus | | Pro-Rata Bonus in Year of Termination | Pro-rated and paid at the end of the period based on actual performance | Pro-rated and paid in a lump sum following the qualifying termination based on Target Bonus | | Equity Award Acceleration | The treatment of unvested equity incentive awards is determined in accordance with the terms of the applicable award agreement | All unvested equity incentive awards that vest solely based on continued employment will accelerate and vest and the treatment of unvested PLUs and PSUs will be determined in accordance with the terms of the applicable award agreement | | Benefits | Health and welfare benefits will be provided for: •18 Months for the Executive Chairman and CEO •12 Months for all other NEOs | Health and welfare benefits will be provided for: •24 Months for all NEOs | | Restrictive Covenants | Post-employment non-compete and non-solicit for: •18 Months for the Executive Chairman and CEO •12 Months for all other NEOs | Post-employment non-compete and non- solicit for: •24 Months for all NEOs |

  53. Treatment of Long-Term Incentive Awards Upon a Termination of Employment

    | | 2026 Proxy Statement 40 |

  54. Treatment of Long-Term Incentive Awards Upon a Termination of Employment

    For additional details on payments that may be due to our NEOs in certain termination scenarios, see “Compensation Tables — Potential Payments to Named Executive Officers Upon Termination and/or Change of Control.” Compensation Decision Process and Methodology Role of the Compensation and Governance Committee The Compensation and Governance Committee is responsible for evaluating the compensation levels for each of our NEOs and for administering the Company’s executive compensation program. The Compensation and Governance Committee reviews and approves all components of executive compensation for our NEOs, including our CEO. In addition, each year the Compensation and Governance Committee reviews and approves the corporate goals and key objectives related to our NEOs’ compensation, evaluates their performance in light of those goals and objectives, and determines and approves their compensation, including for our CEO. Each year the Compensation and Governance Committee also reviews, among other things, proxy season trends and stockholder feedback and the compensation risk assessment. The Compensation and Governance Committee also reviews talent, culture, and sustainable and responsible business practice initiatives; as well as its charter and annual calendar. Compensation Risk Analysis In reviewing the Company’s pay programs, the Compensation and Governance Committee considers whether the programs encourage unnecessary or excessive risk taking that might have an adverse impact on the Company. At the request of the committee, the Company’s independent compensation consultant, Frederic W. Cook & Co. (“FW Cook”), assisted the committee in completing the annual compensation risk assessment of the Company’s compensation programs. The risk assessment included a review of the design and features of the Company’s incentive compensation programs in place, as well as an evaluation of program structure and philosophy, design characteristics, performance management, and governance practices relative to compensation risk factors. The compensation risk assessment resulted in FW Cook and the Compensation and Governance Committee agreeing that the Company’s compensation programs do not create risks that are reasonably likely to have a material adverse effect on the Company. Role of External Compensation and Governance Committee Consultant The Compensation and Governance Committee has the independent authority to hire external consultants, as well as the sole authority to retain and terminate the services of its consultants. As noted, in 2025 the committee engaged FW Cook as its independent consultant. During 2025, FW Cook worked directly under the guidance of the Compensation and Governance Committee, in cooperation with management, to assist the committee with executing its executive compensation-related responsibilities. In such role, the Compensation and Governance Committee’s consultant served as an objective third-party advisor in assessing the reasonableness of compensation levels and the appropriateness of the design of the evolving compensation program structure in supporting the current and future business strategy and human resource objectives. FW Cook attended three of the five formal meetings of the Compensation and Governance Committee during 2025. During 2025, FW Cook supported the Compensation and Governance Committee by assisting with the design and administration of the Company’s executive compensation pay practices, including: •reviewing and providing input on the peer group used to benchmark executive pay; •assessing the market pay data used to inform 2025 pay decisions; •providing input on the pay decisions for the Company’s executive officers, including pay mix and levels; •reviewing and providing input on the Company’s STI and LTI plan designs; •preparing the Company’s compensation risk assessment; •reviewing and providing input on the Company’s compensation philosophy; •providing a review and recommendation for non-employee director compensation; and •keeping the Compensation and Governance Committee informed of changes in the regulatory or governance environment for executive compensation issues. The Compensation and Governance Committee was provided compensation market data and analysis from FW Cook. The committee used that data and analysis to ensure that the compensation practices were consistent with the compensation philosophy and objectives for both the amount and composition of executive compensation. Based on the data and analysis provided by FW Cook, as well as information from management and outside counsel, the committee applied business

  55. Treatment of Long-Term Incentive Awards Upon a Termination of Employment

    | | 2026 Proxy Statement 41 |

  56. Treatment of Long-Term Incentive Awards Upon a Termination of Employment

    judgment in recommending and approving compensation awards, taking into account the dynamic nature of the businesses and the adaptability and response required by senior leadership to manage change. Other than serving as the consultant to the Compensation and Governance Committee, FW Cook provides no other services to the Company. The committee determined that, based on the factors specified in the NYSE listing rules, FW Cook’s services produced no conflicts of interest, and it is an independent advisor to the Compensation and Governance Committee. Role of our Executive Chairman, CEO, and Management Our Executive Chairman and CEO do not participate in the Compensation and Governance Committee’s determination of their individual compensation. They do, however, make recommendations to the committee for each of the other NEOs. The Executive Chairman and CEO base these recommendations on overall Company financial performance for the fiscal year as described above along with their informed assessment of each NEO’s individual performance and contributions. The Compensation and Governance Committee reviews and considers the Executive Chairman’s and CEO’s recommendations, makes adjustments, if any, as it determines appropriate, and approves compensation in its sole discretion. Use of Peer Company Data In making its determinations for the year ended December 31, 2025, the Compensation and Governance Committee considered publicly available information of a select group of peer companies, as well as survey data from the Company’s compensation surveys to inform the pay levels and structures for the Company’s executive officers. All compensation data used was supported by FW Cook as the Compensation and Governance Committee’s independent compensation consultant. The peer group was selected by the Compensation and Governance Committee, in consultation with FW Cook and input from management, on the comparability of the business operations of potential peer group companies, including reasonably comparable size (based on revenue and market capitalization) and industry. Information about the peer group companies was used to inform decisions regarding pay levels and mix and program design. For conducting a competitive assessment of the compensation levels for the Company’s executives for fiscal year 2025, the Compensation and Governance Committee approved the below peer group of 15 companies. Argo Group International Holdings, Ltd. was removed from the list used in 2024 due to merger and acquisition activity involving that company and BRP Group, Inc. changed its name to Baldwin Insurance Group, Inc. Otherwise the list is unchanged from the prior year.

  57. Treatment of Long-Term Incentive Awards Upon a Termination of Employment

    | •Aon PLC •Arthur J. Gallagher & Co. •AXIS Capital Holdings Limited •Baldwin Insurance Group, Inc •Brown & Brown, Inc. •CBIZ, Inc. •Crawford & Co. •Erie Indemnity Company | •Goosehead Insurance, Inc. •Hanover Insurance Group, Inc. •Marsh & McLennan Companies, Inc. •Primerica, Inc. •RLI Corp. •Selective Insurance Group, Inc. •Willis Towers Watson PLC |

  58. Treatment of Long-Term Incentive Awards Upon a Termination of Employment

    | | 2026 Proxy Statement 42 |

  59. COMPENSATION TABLES AND DISCLOSURE

    | Name and Principal Position | Year | Salary ($) | Bonus ($) | Stock Awards ($)(1) | Option Awards ($) | Non-Equity Incentive Plan Compen- sation ($)(2) | All Other Compen- sation ($)(3) | Total ($) | | Patrick G. Ryan | 2025 | 1,233,654 | — | — | — | — | 13,947 | 1,247,601 | | Founder and Executive Chairman of the Board | 2024 | 1,375,000 | — | — | — | 2,597,237 | 13,014 | 3,985,251 | | | 2023 | 1,375,000 | — | — | — | 2,870,450 | 11,250 | 4,256,700 | | Timothy W. Turner | 2025 | 1,442,308 | — | — | — | — | 11,750 | 1,454,058 | | Chief Executive Officer | 2024 | 1,200,000 | — | 2,470,256 | — | 2,266,679 | 11,500 | 5,948,435 | | | 2023 | 1,200,000 | 194,880 | — | — | 2,505,120 | 47,529 | 3,947,529 | | Janice M. Hamilton | 2025 | 600,000 | — | — | — | 374,000 | 11,750 | 985,750 | | Chief Financial Officer | 2024 | 429,845 | 850,005 | 2,756,259 | — | — | 12,940 | 4,049,049 | | Stephen P. Keogh | 2025 | 385,385 | — | 1,999,985 | — | 187,000 | 11,750 | 2,584,120 | | Co-President and Chief Operating Officer | | | | | | | | | | Benjamin M. Wuller | 2025 | 830,769 | — | — | — | 810,900 | 11,750 | 1,653,419 | | CEO Ryan Specialty Underwriting Managers | 2024 | 725,962 | — | 2,349,097 | — | 1,839,399 | 12,940 | 4,927,398 | | Jeremiah R. Bickham (4) | 2025 | 646,346 | — | — | — | 407,899 | 3,852,075 | 4,906,320 | | Former President | 2024 | 649,045 | — | 2,349,097 | — | 1,275,007 | 12,940 | 4,286,089 | | | 2023 | 600,019 | 85,550 | — | — | 939,450 | 11,250 | 1,636,269 |

  60. Compensation Actually Paid and Company Total Stockholder Return

    Compensation Actually Paid and Company Total Stockholder Return The below chart depicts CAP to our PEOs and the average of our Non-PEO NEOs in relationship to our TSR for the same period. Our Non-PEO NEOs’ long-term incentive compensation is directly tied to the increase in value of our common stock.

  61. Compensation Actually Paid and Company Total Stockholder Return

    | | 2026 Proxy Statement 53 |

  62. Compensation Actually Paid and Net Income

    Compensation Actually Paid and Net Income The below chart depicts CAP to our PEOs and the average of our Non-PEO NEOs in relationship to our Net Income for the same period. The Company does not use net income as a performance measure in its overall executive compensation program.

  63. Compensation Actually Paid and Organic Revenue Growth Rate

    Compensation Actually Paid and Organic Revenue Growth Rate The below chart depicts CAP to our PEOs and the average of our Non-PEO NEOs in relationship to our Organic Revenue Growth Rate for the same period. The Company first directly aligned short-term incentive compensation with Organic Revenue Growth Rate in 2022, where 35% of each NEO’s short-term incentive compensation was tied to our Organic Revenue Growth Rate performance and such alignment continued in 2023, 2024, and 2025. See “Executive Compensation: Compensation Discussion and Analysis — Our Executive Compensation Program in Detail — Our Pay Philosophy — Short- Term Incentive Compensation” for further details. An Organic Revenue Growth CAGR also forms an achievement floor for the PSUs and PLUs that were granted to each of our NEOs, other than Mr. Ryan, in 2024 and 2025.

  64. Compensation Actually Paid and Organic Revenue Growth Rate

    | | 2026 Proxy Statement 54 |