DEF 14A of Ryan Specialty Holdings, Inc., Mar 19, 2024

DEF 14A of Ryan Specialty Holdings, Inc.

Filed Mar 19, 2024 · FY20230000950170-24-033106

Open on EDGAR

  1. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    PROPOSAL NO. 1: ELECTION OF DIRECTORS The Board has nominated Patrick G. Ryan, Michelle L. Collins, D. Cameron Findlay and John W. Rogers, Jr. for election as Class III directors; Francesca Cornelli and Anthony J. Kuczinski for election as Class II directors; and Patrick G. Ryan, Jr. for election as a Class I director at the Annual Meeting. Ms. Collins, Dr. Cornelli and Messrs. Ryan, Findlay, Kuczinski, Rogers, Jr. and Ryan, Jr. have each indicated their willingness to serve if elected. Each of Dr. Cornelli and Messrs. Kuczinski and Ryan, Jr. were appointed by the Board since the last annual meeting to serve on the Board until this Annual Meeting. As such, the newly appointed directors will stand alongside the Class III directors for election at this Annual Meeting. 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 diverse attributes 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 recommendation 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. The Compensation and Governance Committee will take into account such factors as diversity, including but not limited to differences in race/ethnicity, creed, color, religious beliefs, gender identity, sexual orientation, and other diversity demographics. The Company is committed to diversity, equity, and inclusion. Nominees and Incumbent Directors The Compensation and Governance Committee has recommended, and the Board has nominated, Ms. Collins and Messrs. Ryan, Findlay, and Rogers, Jr. for election as Class III directors; Dr. Cornelli and Mr. Kuczinski for election as Class II directors; and Mr. Ryan, Jr. for election as a Class I director at the virtual Annual Meeting.

  2. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    | | 2024 Proxy Statement 16 |

  3. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    Class III Directors: Nominees

  4. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    | | Patrick G. Ryan Patrick G. Ryan is a widely respected entrepreneur and global insurance leader who founded Ryan Specialty in 2010. Mr. Ryan has served as the Chairman and Chief Executive Officer of Ryan Specialty since its inception and is the chairperson of the Executive Committee. Prior to launching Ryan Specialty, Mr. Ryan founded Aon Corporation and served as its Chairman and/or CEO for 41 years. At the time of Mr. Ryan’s retirement, Aon had more than 500 offices in 120 countries, generating revenues then in excess of $7 billion. Mr. Ryan has received a number of accolades throughout his career. In 1987, Mr. Ryan received the esteemed Horatio Alger Award, which honors those who are dedicated to the principles of integrity, hard work, perseverance, and compassion for others. In 2008, Mr. Ryan was inducted into the American Academy of Arts and Sciences, one of the nation’s oldest and most prestigious honorary societies and independent research centers, founded in 1780. Also in 2008, he was elected to the International Insurance Society Hall of Fame and received the Ernst and | | Young Entrepreneur of the Year Lifetime Achievement Award. He was named by Brigham Young University International Executive of the Year for Corporate Integrity. Other career tributes include the College of Insurance’s Insurance Leader of the Year and the Insurance Federation of New York’s Free Enterprise Award. Most recently, in July 2019, Mr. Ryan was inducted into the Automotive Hall of Fame for his contribution to the Finance and Insurance Specialists sector of the automotive industry. Mr. Ryan has been a member of Northwestern University’s board of trustees for 42 years, 14 years of which he served as Chairman. Mr. Ryan served on the boards of directors of 1st National Bank of Chicago and its successors and the Tribune Company. Mr. Ryan earned a Bachelor of Business Administration from Northwestern in 1959 and, in 2009, Northwestern awarded Mr. Ryan a Doctor of Humane Letters degree. Also in 2009, Mr. Ryan was inducted into the Northwestern Athletic Hall of Fame. Four years later, in 2013, Mr. Ryan received the Northwestern Alumni Association Medal of Honor. This award is the highest award granted by the Northwestern Alumni Association to an alumnus who combines superior professional distinction and/or exemplary volunteer service to society, with an outstanding record of service to Northwestern. Mr. Ryan also served as Chairman of Chicago 2016, the effort to bring the 2016 Olympic and Paralympic Games to Chicago. We believe that Mr. Ryan’s extensive and industry-leading experience in the area of insurance, his experience as the founder, Chairman and CEO of Aon, and his insight into our business as our Founder and Chief Executive Officer qualifies him to serve on our Board. | |

  5. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    | | 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. | |

  6. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    | | D. Cameron Findlay D. Cameron Findlay has served on our Board since 2012 and is the chairperson of the Compensation and Governance Committee, a member of the Executive Committee and our Lead Director. From 2013 until his retirement in 2023, Mr. Findlay was the Senior Vice President, General Counsel and Secretary of Archer Daniels Midland Company. From 2009 to 2013, he was Senior Vice President and General Counsel of Medtronic, Inc., and from 2003 to 2009 he served as Executive Vice President and General Counsel of Aon Corporation. He earned his B.A. from Northwestern University, his Master of Arts (Oxon.) from Oxford University, and his Juris Doctor from Harvard Law School. We believe Mr. Findlay is qualified to serve on our Board due to his expertise in legal, compliance, and government regulatory matters and his extensive insurance industry experience. |

  7. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    | | 2024 Proxy Statement 17 |

  8. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    | | JOHN W. ROGERS, Jr. John W. Rogers, Jr., has served on our Board since 2014 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 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. | |

  9. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    Class II Directors: Nominees

  10. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    | | Francesca Cornelli Francesca Cornelli has served as a member of our Board since July 2023 and is a member of the Audit Committee. Dr. Cornelli is the dean of Northwestern University’s Kellogg School of Management, a position she has held since August of 2019. She is also a professor of finance and holds the Donald P. Jacobs Chair in Finance. Prior to that, she was a professor of finance and deputy dean at London Business School from 1994 to 2019. Dr. Cornelli’s research interests include corporate governance, private equity, privatization, bankruptcy, IPOs, and innovation policy. She has been an editor of the Review of Financial Studies and previously served on the board of editors of the Review of Economic Studies and as an associate editor at the Journal of Finance. She is a research fellow at the Center for Economic and Policy Research, and previously served as a director of the American Finance Association. Dr. Cornelli has previously taught at the Wharton School of the University of Pennsylvania, the Fuqua School of Business at Duke University, The London School of Economics, | | the Indian School of Business in Hyderabad and the New Economic School in Moscow. Dr. Cornelli currently serves as a member of the board of directors of GCM Grosvenor Inc., a public company, and GCP Capital Partners Limited, an investment company, both engaged in global alternative asset management. She has also served as an independent board member of several global corporations, including Banca Intesa San Paolo from 2016 to 2019, Telecom Italia from 2014 to 2018, American Finance Association from 2013 to 2016, and Swiss Re International and Swiss Re Holdings from 2013 to 2019. In January 2016, she helped create and became a board member of AFFECT, a committee of the American Finance Association designed to promote the advancement of women academics in the field of finance. We believe Dr. Cornelli is qualified to serve on our Board due to her experience as an academic in finance and governance, and her experience on boards of directors of other for-profit companies. | |

  11. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    | | Anthony J. Kuczinski Anthony J. Kuczinski has served on our Board since October 2023 and is a member of both the Audit Committee and the Compensation and Governance Committee. Mr. Kuczinski was the President and Chief Executive Officer of Munich Reinsurance US Holdings from 2008 through 2023. Prior to that, he held numerous senior roles with Munich Re starting in 1989. Prior to Munich Re, Mr. Kuczinski was Chief Operating Officer of NY Marine and General Insurance Company (NYM), a publicly traded insurance group now part of Pro-Sight Insurance Group, and he worked in the audit practice for the public accounting firm of Coopers & Lybrand (now PwC). He currently serves as executive advisor to the Munich Re Board of Management for Munich Reinsurance US Holding, the North American property and casualty operations of Munich Re. Mr. Kuczinski is a director of Skyward Specialty Insurance Group and serves on the Penn Medicine Healthcare System (Penn Medicine) board and on its executive committee. He is also a board member and executive committee chair for Penn Medicine | | Princeton Health, a subsidiary of Penn Medicine. Mr. Kuczinski holds a Bachelor of Arts in Public Accounting from Pace University, Magna Cum Laude, and holds a Certificate in Advanced Executive Education from the Wharton School. Mr. Kuczinski is a Certified Public Accountant and a Chartered Property Casualty Underwriter. We believe Mr. Kuczinski is well qualified to serve on our Board due to his extensive insurance industry and financial experience. | |

  12. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    | | 2024 Proxy Statement 18 |

  13. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    Class I Director: Nominee

  14. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    | | Patrick G. Ryan, Jr. Mr. Ryan, Jr. has served on our Board since January of 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. |

  15. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    Class I Directors: Continuing in Office Until 2025

  16. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    | | Henry S. Bienen, Ph.D Dr. Bienen has served on our Board since 2012 and is a member of both the Audit Committee and the Compensation and Governance Committee. Dr. Bienen served as Northwestern University’s president from 1995 through 2009 and currently serves as president emeritus 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, on the board of directors for Rasmussen University, for which he served in the past as Chairman of the Board, 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 and was the chairman of the board of the Crown Center on the Middle East Studies at Brandeis 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 Bear Stearns Companies, Inc. 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. | |

  17. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    | | 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. |

  18. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    | | 2024 Proxy Statement 19 |

  19. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    | | Timothy W. Turner Timothy W. Turner has served as our President since March 2021, as the Chairman and CEO of RT Specialty since RT’s founding in 2010, and has been a member of our Board of Directors since 2012. Mr. Turner is a member of our 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. | |

  20. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    Class II Directors: Continuing in Office Until 2026

  21. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    | | David P. Bolger David P. Bolger has served on our Board since 2012 and is the chairman of the Audit Committee. Mr. Bolger served as Chief Operating Officer of Chicago 2016, the effort to bring the 2016 Olympic and Paralympic Games to Chicago. From 2004 to 2019, Mr. Bolger served on the board of directors of MB Financial, Inc. From 2003 to 2008, he served as Executive Vice President and Chief Financial Officer of Aon Corporation. Prior to joining Aon, Mr. Bolger served in multiple executive positions at Bank One Corporation and its predecessor companies. He earned a Bachelor of Science in Accounting and Finance from Marquette University and a Master of Management from Northwestern University Kellogg School of Management. We believe Mr. Bolger is qualified to serve on our Board due to his extensive insurance industry, accounting, and finance experience. |

  22. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    | | Nicholas D. Cortezi Nicholas D. Cortezi has served on our Board since our IPO in July 2021 and is a member of the Executive Committee. He served as the Chairman of Ryan Specialty Underwriting Managers from September 2020 through June 2023. In 1987, Mr. Cortezi joined All Risks, Ltd. (“All Risk") and was promoted to CEO in 1999. He served as CEO of All Risks until its acquisition by Ryan Specialty in September 2020. Mr. Cortezi has served on the boards of the Independent Insurance Agents of Baltimore and Maryland, the National Association of Surplus Lines Offices (“NAPSLO”) (now known as the Wholesale & Specialty Insurance Association (“WSIA”)) and was President of NAPSLO between 2002 and 2003. Mr. Cortezi earned a Bachelor of Arts in International Relations and a Masters in International Public Policy from Johns Hopkins University. We believe that Mr. Cortezi's extensive and industry-leading experience in the area of insurance and his insight into our business as prior Chairman of Ryan Specialty Underwriting Managers qualifies him to serve on our Board. |

  23. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    | | Robert (Bobby) Le Blanc Robert (Bobby) Le Blanc has served on our Board since 2018 and is a member of the Compensation and Governance Committee. Mr. Le Blanc joined Onex in 1999 and currently serves as its Chief Executive Officer. Prior to joining Onex, Mr. Le Blanc worked for Berkshire Hathaway and General Electric. He earned his Bachelor of Science from Bucknell University and his Master of Business Administration from New York University. We believe Mr. Le Blanc is qualified to serve on our Board due to his extensive insurance and finance industry experience. |

  24. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    | | 2024 Proxy Statement 20 |

  25. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    The seven nominees who receive the greatest number of affirmative votes cast will be elected as directors for the class in which they are nominated. Upon election, the four Class III directors will 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. Upon election, the two Class II directors will hold office until the 2026 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. Upon election, the one Class I director will hold office until the 2025 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 the nominees named in this Proxy Statement.

  26. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    | | The Board recommends a vote “FOR” the seven director nominees identified above. |

  27. PROPOSAL NO. 1: ELECTION OF DIRECTORS

    | | 2024 Proxy Statement 21 |

  28. 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 2023. 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, and Nicholas D. Cortezi, who was employed by the Company through June 1, 2023, did not receive any additional compensation for their service to the Board while they were employed. Robert Le Blanc has agreed to forgo any cash or equity compensation for his service to 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.

  29. DIRECTOR COMPENSATION

    | Name | Fees Earned or Paid in Cash ($) | Stock Awards ($)(1) | Total ($) | | Henry S. Bienen | $85,000 | $115,000 | $200,000 | | David P. Bolger | 110,000 | 115,000 | 225,000 | | Michelle L. Collins | 85,000 | 115,000 | 200,000 | | Francesca Cornelli (2) | 35,571 | — | 35,571 | | Nicholas D. Cortezi (3) | 49,505 | — | 49,505 | | William J. Devers (4) | 85,000 | 115,000 | 200,000 | | D. Cameron Findlay (5) | 126,389 | 115,000 | 241,389 | | Anthony J. Kuczinski (6) | 14,552 | — | 14,552 | | Robert Le Blanc | — | — | — | | Andrew J. McKenna (7) | 11,611 | 88,895 | 100,506 | | Michael D. O’Halleran | — | 115,000 | 115,000 | | John W. Rogers, Jr. | 85,000 | 115,000 | 200,000 |

  30. DIRECTOR COMPENSATION

    (1) On May 1, 2023, each of the non-employee directors who were serving at that time, other than Mr. Le Blanc and Mr. McKenna, received a grant of 2,814 Restricted Stock Units (“RSUs”) with a grant date fair value of $115,000 as compensation for their year of service to the Company ending at the 2024 annual meeting of stockholders. Mr. McKenna, who passed away on February 7, 2023, received a prorata issuance of Class A common stock for the days that he served. The 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) Dr. Cornelli began her service to the Board on July 31, 2023 and her cash compensation for the 3rd quarter was prorated for the days that she served. (3) Mr. Cortezi retired from his position as the Chief Executive Officer of Ryan Specialty Underwriting Managers on May 31, 2023. Upon his retirement he became a non-employee director and was eligible for compensation under the Company’s Non-Employee Director Compensation Policy. His cash compensation for the 2nd quarter was prorated from the date he became a non-employee director. (4) Mr. Devers retired from the Board on December 31, 2023. (5) Mr. Findlay was appointed to the position of Lead Director on February 22, 2023 after the passing of Mr. McKenna. His cash compensation as Lead Director commencing in the 1st quarter was prorated for the days that he served in that role. (6) Mr. Kuczinski began his service to the Board on October 30, 2023 and his cash compensation for the 4th quarter was prorated for the days that he served. (7) Mr. McKenna passed away on February 7, 2023 and his cash compensation for the 1st quarter and his stock compensation was prorated for the days that he served. In November 2022, after a detailed review of director compensation provided by our peers, the Compensation and Governance Committee amended the Non-Employee Director Compensation Policy to increase (i) the annual cash retainer to $85,000, (ii) the annual grant of equity from a grant date fair value of $110,000 to $120,000, and (iii) the cash retainer for the Chair of the Compensation and Governance Committee from $15,000 to $20,000. All increases were effective on January 1, 2023. Other than the chairperson of the respective Board committees, no participating committee members receive additional compensation for their participation on such committees. In addition to the annual cash retainer, a non-employee director is entitled to additional cash compensation for service as the Lead Director or as the chairperson of a committee as set forth below. Mr. O’Halleran will continue to forgo any cash compensation as a director and Mr. Le Blanc will continue to forgo any cash or equity compensation for his services as a director for the reasons stated above. The annual cash retainer, as well as the Lead Director fee and committee chairperson fee are all paid quarterly.

  31. DIRECTOR COMPENSATION

    | | 2024 Proxy Statement 22 |

  32. DIRECTOR COMPENSATION

    | Committee/Role | Annual Retainer | | Audit Committee Chair | $25,000 | | Compensation and Governance Committee Chair | $20,000 | | Lead Director | $25,000 |

  33. DIRECTOR COMPENSATION

    In addition, our Non-Employee Director Compensation Policy provides that each of our non-employee directors will receive an annual grant of equity. We will grant each of our non-employee directors, with the exception of Mr. Le Blanc, their annual equity grant on the date of the Company’s annual meeting of stockholders. The grants are compensation for the prior year of service. Should any director not serve for the full year covered by the grant (from annual meeting to annual meeting), the grant will be prorated. Each director that served for the entire year through the 2023 annual meeting of stockholders received a grant of equity on May 1, 2023 in the form of RSUs with a grant date fair value equal to $115,000, half the year prorated at $110,000 and half the year at $120,000. 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 grant (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 2023, after a detailed review of director compensation provided by our peers, the Compensation and Governance Committee amended the Non-Employee Director Compensation Policy to increase (i) the annual cash retainer from $85,000 to $100,000, and (ii) the annual grant of equity from a grant date fair value of $120,000 to $125,000. The committee chairperson and Lead Director fees remain unchanged. All increases were effective on January 1, 2024. Stock Ownership Guidelines The Company has non-employee director stock ownership guidelines, under which the Company’s non-employee directors are expected to accumulate Company stock 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 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. 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.

  34. DIRECTOR COMPENSATION

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

  35. DIRECTOR COMPENSATION

    (1) Mr. Cortezi, who has been a director since the IPO, became a non-employee director on June 1, 2023 upon his retirement from his position as Chief Executive Officer of Ryan Specialty Underwriting Managers. Accordingly, all of our directors are currently in compliance with the guidelines.

  36. DIRECTOR COMPENSATION

    | | 2024 Proxy Statement 23 |

  37. 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. | | ✓ | 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 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. |

  38. 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 |

  39. 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 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 |

  40. 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, including the NEOs, were established by the Compensation and Governance Committee in early 2023 following a thorough evaluation of our executive officers’ total compensation and market practices. The Compensation and Governance Committee considers an executive officer’s total compensation when determining any change to a particular component of compensation.

  41. Short-Term Incentive Compensation

    | Named Executive Officer | 2023 Bonus Target % | | Patrick G. Ryan | 200% | | Timothy W. Turner | 200% | | Jeremiah R. Bickham | 150% | | Mark S. Katz | 150% | | Brendan M. Mulshine | 150% |

  42. Short-Term Incentive Compensation

    In early 2023, the Compensation and Governance Committee determined that the actual amount of the 2023 bonuses payable to our NEOs would be determined based on the following criteria, which are composed of both Company based performance metrics and individual, merit-based achievement:

  43. Short-Term Incentive Compensation

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

  44. Short-Term Incentive Compensation

    For the Organic Revenue Growth metric, which is calculated as described in “Appendix A” to this Proxy Statement, payment will be based on the following scale:

  45. Short-Term Incentive Compensation

    | Organic Revenue Growth | Target Payout % | | <5% | 0% | | 12-14% | 100% | | >18% | 150% |

  46. Short-Term Incentive Compensation

    Target payout percentage for Organic Revenue Growth between the benchmarks set forth above will be determined based on a graduated basis. For the Adjusted EBITDAC Margin metric, which is calculated as described in “Appendix A” to this Proxy Statement, payment will be based on the following scale:

  47. Short-Term Incentive Compensation

    | Adjusted EBITDAC Margin | Target Payout % | | <29.00% | 0% | | 30.00-30.25% | 100% | | >31.00% | 150% |

  48. Short-Term Incentive Compensation

    Target payout percentage for Adjusted EBITDAC Margin between the benchmarks set forth above will be determined based on a graduated basis. Individual performance and merit are linked to an individual’s contribution towards (i) culture, (ii) results, (iii) client centricity, (iv) teamwork, and (v) inclusion. Organic Revenue Growth for 2023 was 15.0%, resulting in an STI award of 112.5% of target. Adjusted EBITDAC Margin, based on compensation amounts accrued throughout the year at target, was 30.1%, resulting in an STI award of 100.0% of target. The Compensation and Governance Committee, based on input from Mr. Ryan for each of the NEOs other than Mr. Ryan, determined that based on each NEO’s contribution to the Company's achievement, the Individual Merit-Based Achievement component of each NEO’s

  49. Short-Term Incentive Compensation

    | | 2024 Proxy Statement 31 |

  50. Short-Term Incentive Compensation

    STI award for 2023 would be 100.0% of Target. The Compensation and Governance Committee also determined that Mr. Ryan would receive 100.0% of target for the Individual Merit-Based Achievement component of his STI award based on his contribution to the Company in 2023. As a result, the total STI award for each of our NEOs for 2023 was approximately 104.4% of target. The following table sets forth the STI award payments earned by each of our NEOs in 2023.

  51. Short-Term Incentive Compensation

    | Named Executive Officer | 2023 Bonus Payment | | Patrick G. Ryan(1) | $2,870,450 | | Timothy W. Turner | 2,505,120 | | Jeremiah R. Bickham | 939,450 | | Mark S. Katz | 900,278 | | Brendon M. Mulshine | 1,072,522 |

  52. Short-Term Incentive Compensation

    Mr. Ryan, our founder and CEO, elected, with the consent of the Compensation and Governance Committee, to redirect approximately $900,000 of his discretionary bonus to certain other officers of the Company, including $194,880 to Mr. Turner, $85,550 to Mr. Bickham and $87,222 to Mr. Katz. The Compensation and Governance Committee determined that Target Bonus percentages for 2024 (that will be paid in 2025) will remain the same as they were in 2023 and will be determined based on the Company’s achieving predetermined metrics for Organic Revenue Growth and Adjusted EBITDAC Margin, as well as the Individual Merit-Based Achievement component as determined by the Compensation and Governance Committee.

  53. 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), and (iii) RLUs (as defined below).

  54. 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.

  55. 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). 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. Mulshine (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 Mr. Mulshine’s 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.

  56. Restricted LLC Units

    Restricted LLC Units In March of 2022, each of the NEOs, other than Mr. Ryan, received a grant of restricted LLC units in the LLC (“RLUs”) in recognition of the exceptional performance achieved by the Company in 2021. Each RLU represents the right to receive one LLC Common Unit upon vesting of the RLU. The RLUs vest in equal installments, with the first tranche having vested on April 1, 2023 and the remaining tranches vesting on April 1, 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).

  57. 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 and Reload Class C Units), 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 and Class C Units held by the NEO will continue to vest as if the NEO remained employed with us through each vesting date. Upon any other termination of employment, any unvested LLC Common Units, Staking Class C Units and Reload Class C Units will be forfeited. For the RLUs granted in March 2022, 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 of Mr. Mulshine’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 Mr. Mulshine remained employed with us through such next vesting date and (ii) in the event of Mr. Mulshine’s death or disability, then all of the unvested 2023 Class C Units will continue to vest as if Mr. Mulshine 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. Stock Ownership Guidelines The Board recently 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 his 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 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.

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

    | | 2024 Proxy Statement 33 |

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

    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. Michael L. Conklin, who joined the Company on August 14, 2023, has until August 14, 2028 to meet the guidelines. Accordingly, all of our executive officers are currently in compliance with the guidelines. 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 basis and have it contributed to the plan. Pre-tax 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 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, 2023, none of our NEOs has 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, 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:

  60. 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 | CEO and President: 1.5 X Base Salary and 1.0 X Target Bonus All other NEOs: 1.0 X Base Salary and 1.0 X Target Bonus | All NEOs: 2.0 X Base Salary and 1.0 X 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 |

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

    | | 2024 Proxy Statement 34 |

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

    | | Non-Change-in Control Termination | Change-in-Control Termination | | 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 | | Benefits | Health and welfare benefits will be provided for: • 18 Months for the CEO and President • 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 CEO and President • 12 Months for all other NEOs | Post-employment non-compete and non-solicit for: • 24 Months for all NEOs |

  63. 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, diversity, equity, and inclusion 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 consultant. As noted, in 2023 the committee engaged FW Cook as its independent consultant. During the course of 2023, 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 all of the formal meetings of the Compensation and Governance Committee during 2023. During 2023, 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;

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

    | | 2024 Proxy Statement 35 |

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

    assessing the market pay data used to inform 2023 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 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 CEO and Management Our CEO does not participate in the Compensation and Governance Committee’s determination of his own compensation. He does, however, make recommendations to the committee for each of the other NEOs. The CEO bases these recommendations on overall Company financial performance for the fiscal year as described above along with his informed assessment of each NEO's individual performance and contributions. The Compensation and Governance Committee reviews and considers the 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 fiscal year 2023, 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 executives. 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 2023, the Compensation and Governance Committee approved the below peer group of 16 companies. The companies are the same as the prior year peer group list.

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

    | • Aon PLC • Argo Group International Holdings, Ltd. • Arthur J. Gallagher & Co. • AXIS Capital Holdings Limited • Brown & Brown, Inc. • BRP Group, 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 |

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

    | | 2024 Proxy Statement 36 |

  68. COMPENSATION TABLES AND DISCLOSURE

    | Name and Principal Position | Year | Salary ($) | Bonus ($)(2) | Stock Awards ($) | Option Awards ($)(3) | Non-Equity Incentive Plan Compen- sation ($)(4) | All Other Compen- sation ($)(5) | Total ($) | | Patrick G. Ryan(1) | 2023 | $1,375,000 | — | — | — | $2,870,450 | $11,250 | 4,256,700 | | Founder, Chairman of the Board | 2022 | 1,375,000 | — | — | — | 3,093,745 | 10,250 | 4,478,995 | | and Chief Executive Officer | 2021 | 581,731 | 1,875,000 | — | — | — | — | 2,456,731 | | Timothy W. Turner | 2023 | 1,200,000 | 194,880 | — | — | 2,505,120 | 47,529 | 3,947,529 | | President Ryan Specialty | 2022 | 1,200,000 | — | 729,620 | — | 2,699,996 | 68,836 | 4,698,451 | | Chairman and CEO RT Specialty | 2021 | 1,200,000 | 3,140,000 | 3,839,798 | 528,773 | — | 57,750 | 8,766,321 | | Jeremiah R. Bickham | 2023 | 600,019 | 85,550 | — | — | 939,450 | 11,250 | 1,636,269 | | Chief Financial Officer | 2022 | 600,019 | — | 191,501 | — | 1,012,531 | 10,250 | 1,814,300 | | | 2021 | 535,402 | 1,263,031 | 201,713 | 8,184,369 | — | 9,750 | 10,194,265 | | Mark S. Katz | 2023 | 575,000 | 87,222 | — | — | 900,278 | 11,250 | 1,573,750 | | EVP, General Counsel and Corp | 2022 | 575,000 | — | 183,520 | — | 970,311 | 10,250 | 1,739,081 | | Secretary | 2021 | 557,692 | 1,222,875 | 745,159 | 6,729,995 | — | 15,750 | 9,271,472 | | Brendan M. Mulshine | 2023 | 673,472 | — | — | 1,499,997 | 1,072,522 | 51,398 | 3,297,389 | | Chief Revenue Officer | 2022 | 625,010 | — | 128,248 | — | 1,054,703 | 61,781 | 1,869,742 |

  69. Compensation Actually Paid and Company Total Stockholder Return

    Compensation Actually Paid and Company Total Stockholder Return The below chart depicts CAP to our Principal Executive Officer (“PEO”) 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.

  70. Compensation Actually Paid and Net Income

    Compensation Actually Paid and Net Income The below chart depicts CAP to our PEO 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.

  71. Compensation Actually Paid and Net Income

    | | 2024 Proxy Statement 46 |

  72. Compensation Actually Paid and Organic Revenue Growth

    Compensation Actually Paid and Organic Revenue Growth The below chart depicts CAP to our PEO and the average of our Non-PEO NEOs in relationship to our Organic Revenue Growth for the same period. The Company first directly aligned short-term incentive compensation with Organic Revenue Growth in 2022, where 35% of each NEO’s short-term incentive compensation was tied to our Organic Revenue Growth performance and such alignment continued in 2023. See “Executive Compensation: Compensation Discussion and Analysis — Our Executive Compensation Program in Detail — Our Pay Philosophy — Short-Term Incentive Compensation” for further details.