DEF 14A of Skyward Specialty Insurance Group, Inc., Mar 25, 2026

DEF 14A of Skyward Specialty Insurance Group, Inc.

Filed Mar 25, 2026 · FY20250001519449-26-000021

Open on EDGAR

  1. TABLE OF CONTENTS

    | Outstanding Equity Awards at Fiscal Year-End for Fiscal Year Ended December 31, 2025 | 51 | | Option Exercises and Stock Vested for Fiscal Year Ended December 31, 2025 | 54 | | Potential Payments Upon Termination or Change of Control | 55 | | Pay Ratio | | | Identification of Median Employee Pay Ratio 2025 | | | | 59 | | Pay Versus Performance | 60 | | Director Compensation | 65 | | Equity Compensation Plan Information | 68 | | Certain Relationships and Related Person Transactions | 69 | | Delinquent Section 16(a) Reports | 70 | | Multiple Shareholders Sharing the Same Address | 70 | | Shareholder Proposals | 70 | | Annual Report | 71 | | Other Matters | 71 | | Appendix A - Non-GAAP Reconciliations | A-1 |

  2. DIRECTOR NOMINEES

    DIRECTOR NOMINEES Peter C. Hearn has more than four decades of experience in the global insurance and reinsurance industry. Most recently, he served as Vice Chair of Marsh McLennan from January 2022 to December 2022. Prior to that, Mr. Hearn was Chief Executive Officer of Guy Carpenter & Company, LLC and a member of the Marsh & McLennan Companies Executive Committee from 2015 through 2021. From 2011 to 2015, he served as Global Chairman of Willis Re, having previously held the role of Global Chief Executive Officer from 2005 to 2011 and serving concurrently on the Willis Group Executive Committee. Earlier in his career, Mr. Hearn joined Willis Re in 1994, where he held progressively senior leadership roles, including President. He began his career in reinsurance in 1978 with Willis Faber & Dumas and later joined Towers Perrin Forster & Crosby, where he became a partner in 1986. Mr. Hearn holds a B.A. in history and political science from Lake Forest College. We believe Mr. Hearn is qualified to serve on our Board based on his deep expertise in global reinsurance markets, extensive executive leadership experience, and demonstrated ability to lead complex organizations and drive strategic growth across diversified property and casualty portfolios. Gena Ashe has served on our Board and as Chair of the Nominating and Corporate Governance Committee since August 2023. Since 2019, Ms. Ashe has served as the Chief Legal Officer and Corporate Secretary of Anterix Inc. (NASDAQ: ATEX), a wireless broadband infrastructure company. Since 2021, Ms. Ashe has served as a member of the Board of Directors of the Executive Leadership Council, a non-profit committed to opening channels of opportunity for Black executives to positively impact business and communities, and on which she currently serves as the Vice-Chairman. Previously, Ms. Ashe served on the Board of Directors of GXO Logistics (NYSE: GXO), a publicly traded, global logistics/supply chain outsourcing technology company, and XPO Logistics (NYSE: XPO), a publicly traded, global supply chain solution provider, as Vice Chairman of the Board of XPO Logistics, Europe SA (Euronext: XPO), a France based publicly traded transportation/logistics service provider, and as a Member of the board of ALP Holding Company, a portfolio company of Cold Bore Management. Prior to joining Anterix in 2019, Ms. Ashe held several senior legal roles with prominent firms, including Brightview Services LLC (now known as Brightview Holdings, Inc.), Adtalem Global Education (NYSE:ATGE), Public Broadcasting Service ("PBS"), Darden Restaurants, Inc., AT&T Corp., and Lucent Technologies, Inc. Earlier in her career Ms. Ashe was an electrical engineer and scientist for IBM Corporation before joining IBM's legal team. Ms. Ashe holds a Bachelor of Science from Spelman College, a Master of Science in electrical engineering from Georgia Institute of Technology, and a Juris Doctor from Georgetown University Law Center. We believe Ms. Ashe is qualified to serve as a member of our Board based on her experience, qualifications, attributes, and skills, including her extensive track record of public and private company board service.

  3. CONTINUING DIRECTORS

    CONTINUING DIRECTORS Marcia Dall has served on our Board since November 2022 and as Chair of the Compensation Committee since August 2023. Ms. Dall has served as the Executive Vice President and Chief Financial Officer of Churchill Downs Incorporated, a publicly traded industry-leading racing, online wagering, and gaming entertainment company since October 2015. Prior to this role, Ms. Dall served as Executive Vice President and Chief Financial Officer at Erie Indemnity Company, a company providing sales, underwriting and administrative services to Erie Insurance Exchange, from March 2009 to October 2015. From January 2008 to March 2009, she served as Chief Financial Officer of CIGNA Healthcare. Prior to CIGNA, from August 2002 through January 2008, Ms. Dall was Executive Vice President and Chief Financial Officer for the International and U.S. Mortgage Insurance segments of Genworth Financial, a former subsidiary of GE. Ms. Dall began her career in 1985 in the Financial Management Program at GE and held various leadership roles both in finance and operations over her twenty-plus year tenure with GE. Ms. Dall is a Certified Public Accountant, holds a Bachelor of Science from Indiana University and an MBA from Northwestern University Kellogg School of Management. We believe Ms. Dall is qualified to serve as a member of our Board based on her experience, qualifications, attributes, and skills, including her extensive finance and management background and executive leadership experience in the insurance sector. Anthony J. Kuczinski has served on our Board since August 2023, as our Lead Independent Director since December 2023, and as Chair of the Risk Committee since February 2024. Since July 2024, Mr. Kuczinski has served as a member of the Board of Directors of Hagerty, Inc. (NYSE: HGTY) an automotive enthusiast brand and specialty vehicle insurance provider. Since October 2023, Mr. Kuczinski has served as a member of the Board of Directors of Ryan Specialty Holdings, Inc. (NYSE: RYAN) a service provider of specialty products and solutions for insurance brokers, agents and carriers. From 2008 to 2022, Mr. Kuczinski served as President and Chief Executive Officer of Munich Reinsurance America, Inc. From 1990 to 2007, he served in various roles at Munich Reinsurance America, Inc., including President of the Specialty Markets Division, President of Insurance Company Operations, Executive Vice President and Chief Financial Officer for Specialty Markets, and Senior Vice President. He has over 35 years of industry experience. Mr. Kuczinski is a Certified Public Accountant (Inactive) and a Certified Property Casualty Underwriter and holds a Bachelor of Business Administration from Pace University. We believe Mr. Kuczinski is qualified to serve as a member of our Board based on his experience, qualifications, attributes, and skills including his extensive experience in the insurance industry. Michael Morrissey has served on our Board and as Chair of the Investment Committee since December 2023. Since December 2020, Mr. Morrissey has served as Special Advisor and a member of the executive committee of the International Insurance Society, Inc., a global research organization specializing in the insurance industry, of which Mr. Morrissey served as President and CEO of from May 2009 to December 2020. Since January 2021, Mr. Morrissey has served as Chairman of the Board of Directors of Protective Life Corporation, a Fortune 500 provider of life insurance. Since January 2020, Mr. Morrissey has served as a member of the Board of Directors of Legeis Capital, LLC, an investment advisory firm specializing in the insurance industry. From April 2008 to April 2023, Mr. Morrissey served as a member of the Board of Directors of Selective Insurance Group Inc. (NASDAQ: SIGI), a publicly traded A+ rated, top 40 property and casualty insurer. From May 1983 to May 2009, Mr. Morrissey served as Chairman and CEO of Firemark Investments Inc. (“Firemark”), a former independent investment firm that was focused on the global insurance industry. Prior to founding Firemark, Mr. Morrissey served as President of Manhattan Life Insurance Co. and Senior Vice President of Crum & Forster. Mr. Morrissey holds a Bachelor of Arts from Boston College and an MBA from Dartmouth. We believe Mr. Morrissey is qualified to serve as a member of our Board based on his experience, qualifications, attributes, and skills, including his public board service and extensive insurance and investment market experience. Christopher L. Peirce has served on our Board and as a member of the Audit and Investment Committees since February 2026. Mr. Peirce was appointed as the incoming Chair of the Audit Committee, effective April 1, 2026. From 1995 to 2024, Mr. Peirce served in several financial leadership roles within Liberty Mutual Insurance, a Fortune 100 company, large global property and casualty insurer. During his tenure Mr. Peirce was promoted several times, most recently serving as Executive Vice President and Chief Financial Officer from 2018 to 2024, which included overseeing financial operations, corporate accounting, financial reporting, planning, capital management, actuarial, corporate taxation, treasury, enterprise risk management, global mergers and acquisitions, ceded reinsurance, and leading a team of 700. From 2012 to 2018, Mr. Peirce served as President, Global Specialty. From 2011 to 2012, Mr. Peirce served as President, Commercial Markets. From 2006 to 2011, Mr. Peirce served as CFO, Liberty International. From 1995 to 2006, Mr. Peirce served in other financial leadership roles within the organization. From 1990 to 1995, earlier in his career Mr. Peirce served as Tax Manager at KPMG where he supported a wide range of global business clients across industries on international tax consulting and compliance and earned his CPA Certification. Mr. Peirce is a Certified Public Accountant (Inactive) and holds a Bachelor of Arts in Economics from Harvard University. We believe Mr. Peirce is qualified to serve as a member of our Board based on his experience, qualifications, attributes, and skills, including his extensive financial accounting background and insurance industry expertise. Andrew Robinson has served as our Chief Executive Officer since May 2020, as Chairman of our Board since December 2023, and as a member of our Board since July 2020. Prior to joining Skyward Specialty, Mr. Robinson was an Executive in Residence then Senior Advisor at Oak HC/FT, a venture and growth equity firm, including serving as Co-Chief Executive Officer then as Executive Chair at Groundspeed Analytics, and as Chair of Clara Analytics, both insurance technology companies funded by Oak HC/FT. From January 2017 to July 2017, Mr. Robinson served as the Global Chief Operating Officer and Executive Vice President of Crawford & Company, a claims management solutions business. Mr. Robinson oversaw Crawford & Company's four businesses with revenues of $1.1 billion and over 8,000 employees. Mr. Robinson's experience also includes over ten years with The Hanover Insurance Group, Inc. ("Hanover"), an insurance company, where he rose to President of Specialty Insurance, Executive Vice President of Corporate Development and Chief Risk Officer. While at Hanover, his responsibilities included all aspects of the company's U.S. specialty businesses, including profit and loss and strategic and operational oversight. He was also responsible for acquisitions, divestitures, business integration, and enterprise risk management for the broader enterprise. Prior to his time at Hanover, he was the Managing Partner of Global Insurance at Diamond (now PWC) Consulting. Mr. Robinson also serves on the board of McLarens, Inc., a global insurance services company. Mr. Robinson previously served on the board of directors of Chaucer Plc, a Lloyd's of London managing agency.

  4. CONTINUING DIRECTORS

    Mr. Robinson holds a Bachelor of Science degree from Clarkson University. Mr. Robinson is a highly experienced and successful global insurance executive with a 30-year track record of growth, financial improvement, and strategic and operational leadership. We believe Mr. Robinson is qualified to serve as a member of our Board based on our review of his experience, qualifications, attributes and skills, including his executive leadership experience in the insurance, claims management and technology industries. Katharine Terry has served on our Board and as a member of the Nominating & Corporate Governance Committee since November 2022. Ms. Terry has served as a member of the Audit Committee since August 2023 and as a member of the Risk Committee since its inception in February 2024. Ms. Terry has served as a member of the Compensation Committee since February 2026. Ms. Terry founded Kate Terry and Company, a management consulting firm focused on modernizing insurance products and technology. Prior to that, Ms. Terry cofounded Surround Group, Inc. in June 2018 and served as Chief Operating Officer and Chief Executive Officer. Ms. Terry was Senior Vice President, Commercial Insurance Product Management at Liberty Mutual Insurance from February 2011 through August 2016. She held prior roles in product management at Plymouth Rock Assurance Corporation and Progressive Insurance. Ms. Terry is a Chartered Property and Casualty Underwriter. Ms. Terry holds a Bachelor of Arts from Harvard University and an MBA from Harvard Business School. We believe Ms. Terry is qualified to serve as a member of our Board based on her experience, qualifications, attributes, and skills, including her extensive insurance product management experience.

  5. ELECTION OF CLASS I DIRECTORS

    ELECTION OF CLASS I DIRECTORS Under our governing documents, our Board has the power to set the number of directors from time to time by resolution. We currently have nine authorized directors serving on our Board, of which seven directors are "independent" as defined under the Nasdaq listing standards. In accordance with our certificate of incorporation, our Board is divided into three classes with staggered three-year terms. Any increase or decrease in the number of directors will be distributed among the three classes so that, as nearly as possible, each class will consist of one-third of our directors. This classification of our Board may have the effect of delaying or preventing changes in control of our Company. At the Annual Meeting, two Class I directors will be elected for a three-year term, expiring at our 2029 annual meeting of shareholders or until his or her successor is duly elected and qualified. Based upon the recommendation of our Nominating and Corporate Governance Committee, our Board has nominated the two director nominees set forth below to stand for election by our shareholders.

  6. NOMINEES FOR DIRECTOR

    NOMINEES FOR DIRECTOR Our Nominating and Corporate Governance Committee has recommended, and our Board has approved, Peter C. Hearn and Gena Ashe as nominees for election as Class I directors at the Annual Meeting, with Mr. Hearn’s service as a director commencing August 1, 2026. Robert Creager and James Hays will continue to serve as directors until the Annual Meeting. If elected, Mr. Hearn and Ms. Ashe will serve as Class I directors until the 2029 annual meeting of shareholders or until his or her successors are duly elected and qualified. For information concerning the nominees, please see the section titled "Board of Directors and Corporate Governance — Nominees for Director." If you are a shareholder of record and you vote but do not give instructions with respect to the voting of directors, your shares will be voted "FOR" the election of Mr. Hearn, effective August 1, 2026, and Ms. Ashe, effective as of the Annual Meeting. We expect that Mr. Hearn and Ms. Ashe will accept such nominations; however, in the event that a nominee is unable or declines to serve as a director at the time of the Annual Meeting, the proxies will be voted for any nominee who shall be designated by our Board to fill such vacancy. If you are a beneficial owner of shares of our Common Stock and you do not give voting instructions to your broker, bank or other nominee, then your broker, bank or other nominee will leave your shares unvoted on this matter. VOTE REQUIRED; RECOMMENDATION OF THE BOARD OF DIRECTORS: The election of the Class I directors requires a plurality of the votes cast by the shares of our Common Stock entitled to vote thereon to be approved. Abstentions and broker non-votes will have no effect on this proposal. THE BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS A VOTE "FOR" THE ELECTION OF THE DIRECTORS NOMINATED BY OUR BOARD OF DIRECTORS AND NAMED IN THIS PROXY STATEMENT AS CLASS I DIRECTORS TO SERVE FOR THREE-YEAR TERMS EXPIRING AT THE 2029 ANNUAL MEETING.

  7. Aligning 2026 Organizational Structure and Compensation Programs to Support Integrated Business Priorities

    | New Employment Agreements with Key Executives | We entered into new employment agreements with Andrew Robinson (Chairman and Chief Executive Officer, Skyward Group) and John Burkhart (President, U.S. Property and Casualty, Skyward Specialty) in connection with the updated organizational structure, expanded responsibilities, and the Company’s increased size following the Apollo acquisition and made the following compensation changes: •Mr. Robinson's 2026 Compensation: Base salary of $1,100,000; target annual incentive opportunity of 150% of base salary; target long-term incentive opportunity of $4,000,000 •Mr. Burkhart's 2026 Compensation: Base salary of $600,000; target annual incentive opportunity of 100% of base salary; target long-term incentive opportunity of $1,000,000 | | Incentive Plan Changes | 2026 Short-Term Incentive Plan (“STIP”): •Skyward Group executives: 70% based on group GWP growth and combined ratio; 30% based on individual performance (OKRs) •Skyward Specialty executives: 100% based on Skyward Specialty GWP growth and combined ratio, subject to OKR adjustment •Maximum payout cap of 200% of target added to both programs 2026 Long-Term Incentive Plan: •Combined ratio PSUs measured on consolidated Skyward Group results for Group executives and on Skyward Specialty results for Skyward Specialty executives •Growth in book value per share PSUs measured on consolidated Skyward Group results for all executives •Maximum payout cap of 200% of target added to both PSU programs |

  8. ADDITIONAL POLICIES AND BENEFITS

    | WHAT WE DO | | WHAT WE DON’T DO | | | ✓ | Grant compensation that is primarily variable and tied to Company performance goals and stock price | × | No hedging or pledging of Company stock | | ✓ | Performance metrics support our strategy and align executive interests with those of our shareholders | × | No guaranteed equity award levels | | ✓ | Use an independent compensation consultant | × | No executive perquisites | | ✓ | Maximum payouts of PSUs are capped | × | No supplemental executive retirement plans | | ✓ | Structure compensation policies and practices to mitigate excessive risk taking | × | No tax gross-ups in connection with a change in control and no automatic single trigger vesting | | ✓ | Use compensation reference group data for assessing and setting executive compensation target amounts | × | No repricing of stock options or stock appreciation rights without shareholder approval | | ✓ | Maintain corporate governance guardrails, including a recoupment policy and stock ownership guidelines | × | No excessive severance benefits |

  9. ADDITIONAL POLICIES AND BENEFITS

    Policies and Practices Related to the Timing of Grants of Certain Equity Awards. The Company does not grant equity awards when in possession of material non-public information. The Company generally makes broad-based equity grants at approximately the same time each year in late February, after earnings are released, as recommended by the Committee at their regularly scheduled meeting and approved by the Board on the following date; however, the Company may choose to make equity grants outside of the annual broad-based grant (e.g., as part of a new hire package or as a retention or promotional incentive). Any stock options would be granted with an exercise price based on the fair market value on the date of grant. With respect to the grants of RSUs and PSUs prior to the 2025 grants, the values of the target grant amounts were based on the Company’s average closing price of the ten open trading days preceding the date of the Committee’s meeting, which was one day prior to the grant date. Beginning with the 2025 grants, the values of the target grant amounts are based on the Company’s average closing price of the five open trading days preceding the date of Committee’s meeting, which is one day prior to the grant date. The Company chooses to use an average closing price in order to mitigate any short-term volatility in share price. Restrictions on Hedging or Pledging. Our Securities Trading Policy applies to all of our employees, including our NEOs and directors. The policy, among other things, prohibits engaging in short-term or speculative transactions involving Company securities, such as short sales, puts and calls, hedging, pledging, and holding Company securities in a margin account. Clawback and Forfeiture Policy. We maintain a clawback policy in compliance with Dodd-Frank and listing exchange rules, pursuant to which the Committee may recover (including by means of recoupment and/or forfeiture of unvested amounts) covered incentive compensation from a current or former executive officer, to the extent that the recipient receives any amount in excess of the amount that the recipient should otherwise have received under the terms of the award or payment as a result of a financial restatement, during the three years immediately preceding the year in which such restatement is required. Compensation covered by this policy includes any compensation (cash and equity) that is earned, granted, or vested based wholly or in part upon the attainment of any financial reporting measure. In addition, pursuant to the terms of our 2022 Long-Term Incentive Plan, all of our equity awards granted thereunder (including time- and performance-based awards) are subject to our clawback policy, as it may be amended from time to time. Stock Ownership Guidelines. Executive officers and other executive leadership team (“ELT”) members are required to hold a certain portion of their base cash compensation in Skyward Specialty stock and to comply with the related stock retention guidelines, as follows:

  10. ADDITIONAL POLICIES AND BENEFITS

    A covered executive has five years to comply with the guidelines. ELT members (which includes the NEOs) must hold 50% of their after-tax shares until the guideline is met, and if not in compliance after the five-year initial period, the executive must retain 100% of his or her after-tax vested shares until the ownership guideline is satisfied. For purposes of measuring compliance, shares owned outright or beneficially owned and unvested time-based RSUs “count” towards the guidelines, whereas unexercised stock options and unearned performance-based equity awards, including PSUs, do not count. Other Benefits. The Company provides certain additional benefits to executive officers that are also generally available to employees, which may be modified from time to time but currently include medical, dental, vision and life insurance coverage, 401(k) matching contributions and an Employee Stock Purchase Plan. Executives pay the same premiums for medical, dental, vision, and life insurance coverage as all employees. Perquisites and Other Personal Benefits. Currently, we do not provide any perquisites or other personal benefits to our executives.

  11. NEO Severance Arrangements for Fiscal Year 2025

    NEO Severance Arrangements for Fiscal Year 2025 We provide our NEOs with certain payments and benefits upon qualifying terminations of employment, provided specified requirements are met. For our CEO, these benefits are documented in his employment agreement and for our other executives, in their severance agreements and their individual award grants. The severance benefits are an essential element of the overall executive compensation package and assist the Company in recruiting and retaining talented individuals and aligning the executive’s interests with the best interests of the shareholders. Additional detail regarding the payments due upon certain terminations of employment are described below under “Potential Payments Upon Termination or Change in Control.”

  12. Outstanding Performance in Fiscal Year 2025 Supported by Compensation Program Design

    | Majority of Executive Compensation is Delivered in the Form of Variable Compensation | | | Incentive Plan Metrics Align with Key Business Priorities | Our Short-Term Incentive Plan (“STIP”) incorporates performance goals based on a calendar year internal combined ratio(1) ("CR") target along with a growth in gross written premiums (“GWP”) target, which incentivizes profitable growth. Two types of performance-based stock unit (“PSUs”) awards were granted and are eligible to vest based on the level of the Company’s (i) relative growth in book value per share (“GBVPS”) over three years, and (ii) three-year internal CR(1). | | Incentive Plans Aligned with Company Performance | STIP payout of 150% of target based on 24.2% growth in GWP and an adjusted CR(1) of 89.6% along with exceptional achievement of our OKRs. 2023-2025 relative growth in book value per share GBVPS PSU awards completed their three-year performance period and will be eligible to be earned based on their applicable relative ranking to our peers, as further described below. 2023-2025 CR PSU awards completed their three-year performance period and were earned at 116% of target based on the three-year average adjusted CR(1) of 90.9%. |

  13. Outstanding Performance in Fiscal Year 2025 Supported by Compensation Program Design

    (1) For purposes of evaluating our performance-based compensation, we adjust the externally reported CR to (i) include the impact of IPO related stock compensation and secondary offering expenses, and (ii) exclude certain non-recurring charges associated with the loss portfolio transfer ("LPT"). See Appendix A - Non-GAAP Reconciliations on page A-1 at the end of this Proxy Statement for further information. We regularly review our executive compensation program to ensure that it continues to support our compensation philosophy and our business needs. In addition, we continue to assess the ways in which we can provide direct links between pay and the enhancement of shareholder value. Role of the Compensation Committee. Our Compensation Committee consists of three independent directors and is principally responsible for administering the executive compensation program, including with respect to our NEOs. The Committee considers a number of factors in setting compensation for its executive officers, including an executive’s individual performance, experience and responsibilities, the compensation of executive officers in similar benchmark positions, as provided by Frederic W. Cook & Co., Inc. (“FW Cook”), the Committee's independent compensation consultant, internal equity, the aggregate amount of compensation that may be realized, compensation trends in the market, and Company performance. The primary responsibilities of the Committee are set forth in detail on page 13 of this Proxy Statement and in the Compensation Committee Charter, which can be found on our website under the Corporate Governance tab at https://investors.skywardinsurance.com/corporate-governance/governance-overview. Role of the Chief Executive Officer. Each year our CEO assesses the performance of each executive officer, excluding himself, and makes recommendations to the Committee regarding the compensation of each executive. Such recommendations are based on various factors as discussed above. Our CEO also provides an evaluation of the most recently completed fiscal year. The Committee reviews and considers the CEO’s assessment and executive officer compensation recommendations in totality with other inputs as described herein, when determining our NEOs compensation. This process excludes our CEO's compensation, which is determined exclusively by the independent directors of the Board. Role of the Independent Compensation Consultant. The Committee has the sole authority to retain and replace compensation consultants to provide it with independent advice, and the Committee believes that independent advice is essential in developing the Company’s executive compensation programs. The Committee engaged FW Cook during fiscal year 2025 as its independent consultant to advise on matters related to the Company’s executive compensation program and the compensation for our non-employee directors. FW Cook provides support at the Committee’s direction, including with respect to regulatory developments, marketplace trends and best practices for executive compensation, and competitive pay levels. Our compensation consultant reports directly to the Committee. The Committee assesses our compensation consultant’s independence annually in accordance with SEC and Nasdaq rules and confirmed that FW Cook’s work did not raise any conflicts of interest and that FW Cook is independent under applicable rules. Compensation Reference Group. In fiscal year 2024, based on advice provided by FW Cook, the Committee considered executive compensation data that included data from the following companies, with whom we compete for talent, which provided market context for the Committee’s decisions related to our 2025 executive compensation levels and program design: AMERISAFE, Employers Holdings, Hamilton Insurance, James River Group, Kinsale Capital Group, Palomar Holdings, ProAssurance, RLI, Safety Insurance Group, SiriusPoint, Tiptee, Trisura, United Fire Group, and Universal Insurance. Argo Group International and Global Indemnity were removed from the reference group following Argo Group’s acquisition by Brookfield Reinsurance and due to Global Indemnity’s ownership structure. Hamilton Insurance was added to the compensation reference group due to its comparable size and having recently become a publicly traded company similar to Skyward Specialty. This list includes companies that exhibit similar business characteristics that influence executive pay and provide context to the market value of the executive role. At the time the comparative analysis was prepared, we were positioned near the median of the reference group data for gross written premiums and market capitalization. The Committee considers the compensation reference group data as one of several reference points to inform its decisions about overall compensation opportunities and specific compensation elements. We also supplement this data with published compensation surveys where appropriate. The Committee does not benchmark specific compensation elements or total compensation to any specific percentile and compensation decisions are made on a case-by-case basis. We believe the use of compensation reference group information enables the Committee to create better alignment between pay and performance and helps attract and retain executive leaders.

  14. COMPONENTS OF OUR EXECUTIVE COMPENSATION PROGRAM

    COMPONENTS OF OUR EXECUTIVE COMPENSATION PROGRAM Direct compensation for our NEOs primarily consists of base salary, annual cash incentive bonus opportunities, and long-term incentives. Base Salary. In February 2025, the Committee reviewed the base salaries of our NEOs and evaluated whether to increase base salaries after taking into account market conditions, performance, and the Company’s compensation philosophy. The Committee determined to increase the base salaries of Messrs. Robinson and Kapadia by the amounts reflected in the chart below in order for their base salaries to be reflective of market levels. Mr. Haushill’s and Mr. Burkhart’s base salaries were benchmarked against the market, and after such analysis the Committee determined they remained appropriate; therefore, no changes were made to their base salaries for fiscal year 2025. Base salaries are reviewed annually, typically in connection with the annual performance review process, and may be further adjusted from time to time on account of promotion or otherwise deemed appropriate by the Committee. The base salaries for the NEOs depicted below generally became effective April 1, 2025. Mr. Kapadia’s base salary was first increased from $400,000 to $425,000, effective April 1, 2025 and then further increased from $425,000 to $450,000 effective August 1, 2025, in connection with his promotion to President, Reinsurance and Head of Actuarial on August 1, 2025. Ms. Ryan was hired on March 10, 2025 and appointed General Counsel and Corporate Secretary effective April 1, 2025 at which time her salary was set at $375,000 in order to be competitive relative to market for such position.

  15. COMPONENTS OF OUR EXECUTIVE COMPENSATION PROGRAM

    Annual Cash Incentive. The Committee believes that performance-based cash bonuses are an appropriate component in the overall compensation program, and that such incentive opportunities motivate executives to achieve our short-term financial and operational objectives. Each NEO has a target annual cash bonus opportunity, expressed as a percentage of base salary. The Committee assesses and determines whether to modify the target amounts annually, using the factors that are applied for the determination of executive officer compensation, as described above. After careful review, the Committee determined to increase certain of the NEO bonus targets as a percentage of base salary for 2025, based on several factors, including market conditions, performance, and the Company’s compensation philosophy, so that a greater percentage of our NEOs cash compensation would be performance incentive compensation. Ms. Ryan was hired on March 10, 2025 and appointed General Counsel and Corporate Secretary effective April 1, 2025 at which time her target annual cash bonus opportunity was set at 50% of base salary, which was determined to be competitive relative to market for such position. With respect to our NEOs, the targets were increased as reflected in the chart below:

  16. COMPONENTS OF OUR EXECUTIVE COMPENSATION PROGRAM

    | Named Executive Officer | 2025 Bonus Target (% of Base Salary) | Bonus Target ($) | 2024 Bonus Target (% of Base Salary) | | Andrew Robinson | 150 | 1,500,000 | 125 | | Mark Haushill | 80 | 400,000 | 60 | | John Burkhart | 80 | 400,000 | 60 | | Sandip Kapadia | 65 | 292,500 | 40 | | Patricia Ryan | 50 | 187,500 | -- |

  17. COMPONENTS OF OUR EXECUTIVE COMPENSATION PROGRAM

    In addition to the Company’s primary focus on profitable growth, the 2025 STIP performance goals also included as performance goals the Company’s achievement of its OKRs (our top down set of strategic and operational Objectives and Key Results). The Committee first evaluates performance relative to the operating performance and growth matrix to determine the corresponding performance score. The Committee may adjust the NEO award amount based upon under-or over-achievement of the OKRs and other factors as determined in the Committee's sole discretion. For 2025, we delivered exceptional performance against our OKRs, including delivering strong underwriting results and premium growth; strengthening financial processes and controls with no material weaknesses and a clear plan to address process enhancements; leveraging data and technology to improve risk selection fidelity, pricing efficacy, claims outcomes and operational efficiency; continuing our portfolio development into less cycle-exposed lines of business and reducing liability durations, launching compelling new niche market offerings; executing on our succession next level readiness, hiring plan and early-career talent programs. While these specified performance goals and guidelines serve as the primary starting point for the Committee's determination of the applicable STIP award for our NEOs, the Committee ultimately determines the applicable STIP award amount in its discretion and after considering other factors, including our overall performance and the NEO's individual performance. The Committee retains discretion to approve STIP awards that are above or below the performance achievement level referenced in the guidelines, including the discretion to award no STIP bonus amount to any NEO for any fiscal year. In January 2026, the Committee determined that our 2025 performance goals were significantly exceeded resulting in a performance factor of 150% of target based upon 24.2% growth in GWP and internal CR of 89.6%, along with the exceptional achievement of our OKRs as noted above. The Board approved the CEO’s STIP payment amount, and the Committee determined the STIP payment amounts for our other NEOs after considering the CEO's recommendations for those NEOs other than himself, and after considering our level of achievement of the OKRs and the NEO's individual performance. The approved target bonus payout percentages and actual amounts paid to our NEOs for performance in 2025 are set forth in the following table:

  18. COMPONENTS OF OUR EXECUTIVE COMPENSATION PROGRAM

    | Named Executive Officer | Actual Annual Bonus (% of Target) | Actual Annual Bonus ($) | | Andrew Robinson | 175 | 2,625,000 | | Mark Haushill | 150 | 600,000 | | John Burkhart | 187 | 750,000 | | Sandip Kapadia | 137 | 400,000 | | Patricia Ryan | 267 | 500,000 |

  19. COMPONENTS OF OUR EXECUTIVE COMPENSATION PROGRAM

    Under the terms of the Short-Term Incentive Plan, the Committee retains discretion to approve annual cash awards above the Company’s overall performance factor in order to recognize extraordinary individual performance. For 2025, the Committee approved annual bonus payouts of $2,625,000 to Mr. Robinson and $500,000 to Ms. Ryan to recognize their exceptional performance in connection with the Apollo transaction and related integration efforts. Mr. Burkhart received an annual bonus payout of $750,000 in recognition of his role in leading Skyward Specialty to our best year on record. The Committee or Board may, from time to time, approve other discretionary or formulaic annual cash awards based on performance, for new hires, promotions or retention, or as otherwise determined appropriate. In March 2025, in connection with Ms. Ryan joining the Company, she received a one-time cash sign-on bonus in the amount of $150,000, which replaced the value of the unvested equity awards that Ms. Ryan forfeited when she left her previous employer. Long-Term Equity Incentives. We believe equity grants are an integral part of our executive compensation program, as they provide a strong link to long-term performance, create retention incentives and a culture of ownership, and also align the interests of executive officers with those of our shareholders. Our general practice is to award annual grants as part of the regular program in February of each year. The size and value of annual equity awards are based on considerations included in the process for determining executive compensation, as described in more detail above. We may also grant equity awards at other times of the year in the Committee’s discretion, for example at the time of hire, promotion, or for other special circumstances. Ms. Ryan was granted a new hire equity award on May 7, 2025, at the first Compensation Committee meeting following her date of hire, in order to give her a meaningful equity stake that would provide a retention incentive and set her equity compensation at levels competitive with our peers. For fiscal year 2025, our Committee determined to grant the NEOs equity awards consisting of a mix of approximately 67% PSUs, where equal amounts are eligible to vest based on our level of GBVPS and internal CR attainment over the applicable three-year performance periods, and 33% time-based vesting RSUs. 2025 RSUs. The RSUs granted to our NEOs in fiscal year 2025 are eligible to vest on January 1, 2028, subject to continued employment (except in the case of certain qualified terminations of employment, pursuant to the terms and conditions of the individual award agreements, as further described below under “Potential Payments Upon Termination or Change in Control”). We grant time-based RSUs to support retention and align interests of executives with shareholders as the underlying value of the awards increases with increases in our stock price. 2025 PSUs. The PSUs granted to our NEOs in fiscal year 2025 are eligible to vest, subject to continued employment through December 31, 2027 and meeting certain predetermined performance goals for the three-year performance period ending December 31, 2027. In certain cases, the awards are also eligible to vest earlier upon a qualifying termination of employment, as described in more detail below. The maximum number of PSUs that may vest is capped at 150% of the target number of PSUs. Half of the 2025 PSUs (or approximately 33% of the target value of the aggregate long-term equity grants to the NEOs) are subject to a three-year internal CR performance goal, with the number of units eligible to vest determined based on performance results. The remaining half of the PSUs are subject to our GBVPS performance goal as determined based on the level of performance reported in our Company’s year-end GAAP financial statements, as determined by the Committee, and relative to that of a peer group of comparison companies. The relative GBVPS performance level will be determined as a straight-line average of the GBVPS at each year-end of the three-year performance period, as further illustrated in the tables below.

  20. COMPONENTS OF OUR EXECUTIVE COMPENSATION PROGRAM

    After careful consideration of market data and the various factors described earlier in this CD&A regarding the determination of executive compensation, for the 2025 equity grants, the Committee approved to increase the target annual equity value for certain of our executives as compared to the prior year. The Committee determined that these increases were appropriate to help position the executives closer to the market median for their total and performance incentive compensation, while also strengthening the alignment of our executive’s economic interests with our shareholders. There was no increase to the target annual equity value for Mr. Robinson as it was determined that his long-term incentive target value remained competitive to market. Ms. Ryan was hired on March 10, 2025, and appointed General Counsel and Corporate Secretary effective April 1, 2025 at which time her target annual equity value was set at $175,000, which was determined to be competitive to market for such position. A summary of the target grant value of the 2025 equity awards for our NEOs is as follows:

  21. COMPONENTS OF OUR EXECUTIVE COMPENSATION PROGRAM

    | Named Executive Officer | 2025 Target Long-Term Incentive Target Value ($) | 2024 Target Long-Term Incentive Target Value ($) | Percentage Increase (%) | | Andrew Robinson | 1,500,000 | 1,500,000 | 0 | | Mark Haushill | 400,000 | 350,000 | 14 | | John Burkhart | 400,000 | 350,000 | 14 | | Sandip Kapadia | 225,000 | 175,000 | 29 | | Patricia Ryan | 175,000 | -- | -- |

  22. Vesting of 2023-2025 Long-Term Incentive Awards

    Vesting of 2023-2025 Long-Term Incentive Awards In 2023, we granted performance-based equity awards (“the 2023-2025 PSUs”) based on either relative GBVPS or internal CR, in each case measured over a three-year performance period ending December 31, 2025.

  23. Performance Vesting Results for 2023 PSU Grants

    Performance Vesting Results for 2023 PSU Grants

  24. 2023-2025 CR PSUs

    2023-2025 CR PSUs 2023-2025 PSUs have a performance scale linked to achieved internal CR for a three-year performance period ending December 31, 2025. These PSUs were eligible to vest subject to the applicable level of attainment of the CR performance goal and the NEO's continued services with us through the date the Compensation Committee certifies results (which occurred in 2026). For the 2023-2025 CR PSU awards, the target internal CR achievement level to receive at payout at 100% of the target award amount was a 92.5 internal CR. The achieved internal CR for each of the three fiscal years (“Measurement Periods”) that comprise the three-year performance period, are averaged and a performance factor is determined with respect to the performance scale, which can vary from 0% to 150% of the target number of PSUs. For the 2023-2025 PSU awards, the average internal CR achieved for the 2023-2025 performance period was 90.9% and the corresponding vesting level of the PSUs was at 116% of the target number of PSUs. Accordingly, our NEOs vested in the applicable number of 2023-2025 PSUs as set forth in the chart below:

  25. 2023-2025 CR PSUs

    | Named Executive Officer | Target PSUs (#) | Earned PSUs (#) | | Andrew Robinson | 15,151 | 17,575 | | Mark Haushill | 3,787 | 4,392 | | John Burkhart | 3,619 | 4,198 | | Sandip Kapadia | 2,020 | 2,343 |

  26. 2023-2025 Relative GBVPS PSUs

    2023-2025 Relative GBVPS PSUs Four of our NEOs received relative 2023-2025 PSUs with respect to the target and maximum number of PSUs set forth in the chart below. These PSUs are eligible to vest subject to the Committee’s determination of the applicable level of attainment of the relative GBVPS performance goal and the NEO’s continued services with the Company through December 31, 2025, which was satisfied. The average performance factor for the three annual measurement periods of the 2023-2025 PSUs based on relative GBVPS during the three-year performance period ending December 31, 2025, cannot be calculated until all of the applicable peer book value per share data for fiscal year 2025 is publicly available, which is anticipated to occur sometime in May 2026.

  27. 2023-2025 Relative GBVPS PSUs

    | Named Executive Officer | Target PSUs (#) | Maximum PSUs (#) | | Andrew Robinson | 15,151 | 22,726 | | Mark Haushill | 3,787 | 5,680 | | John Burkhart | 3,619 | 5,428 | | Sandip Kapadia | 2,020 | 3,030 |

  28. 2023-2025 Relative GBVPS PSUs

    The three-year performance period for the relative GBVPS 2023-2025 PSUs includes three annual measurement periods, the performance of which is averaged for purposes of determining the applicable performance and vesting level. For the 2023 measurement period, Alleghany, Argo, Hallmark Financial, and Trean were removed from the peer group due to them no longer being publicly traded companies and were replaced with Employers Insurance Group, Palomar, and SiriusPoint. For each annual measurement period, we assess our relative peer position and apply that position against a performance scale which can vary from 0% to 150%, with target performance corresponding to the 50th percentile, to determine the corresponding performance factor and applicable vesting level.

  29. 2025 SUMMARY COMPENSATION TABLE

    2025 SUMMARY COMPENSATION TABLE The following table shows for the years ended December 31, 2025, 2024 and 2023, compensation awarded to or paid to, or earned by, the NEOs, which consist of our Chief Executive Officer, Chief Financial Officer and our three other most highly compensated executive officers at December 31, 2025.

  30. 2025 SUMMARY COMPENSATION TABLE

    | Name and Principal Position(1) | | Fiscal Year | Salary ($) | Bonus ($) | Stock Awards ($)(2) | Option Awards ($)(3)(4) | Non-Equity Incentive Plan Compensation ($) | All Other Compensation ($)(5) | Total ($) | | Andrew Robinson | | 2025 | 975,000 | — | 1,563,117(6) | — | 2,973,000(7) | 21,000 | 5,532,117 | | | Chairman and CEO, Skyward Group | 2024 | 900,000 | — | 1,634,869(8) | — | 2,107,000(9) | — | 4,641,869 | | | | 2023 | 800,000 | — | 3,877,243(10) | 2,328,000 | 1,600,000(11) | 16,500 | 8,621,743 | | Mark Haushill | | 2025 | 500,000 | — | 416,811(12) | — | 687,000(13) | 30,333 | 1,634,144 | | | CFO, Skyward Group | 2024 | 487,500 | — | 381,422(14) | — | 534,000(15) | 3,750 | 1,406,672 | | | | 2023 | 450,000 | — | 619,168(16) | 310,381 | 360,000(11) | 16,500 | 1,756,049 | | John Burkhart | | 2025 | 500,000 | — | 416,811(17) | — | 827,333(18) | 31,208 | 1,775,352 | | | President, U.S. Property and Casualty, Skyward Specialty | 2024 | 464,584 | — | 381,422(19) | — | 450,000(20) | 3,542 | 1,299,548 | | | | 2023 | 418,750 | 21,000(21) | 609,440(22) | 310,381 | 450,000(23) | 16,500 | 1,826,071 | | Patricia Ryan (24) | | 2025 | 304,688 | 150,000(25) | 185,056(26) | — | 500,000(27) | 14,063 | 1,153,807 | | | Chief Legal Officer and Corporate Secretary, Skyward Group | | — | — | — | — | — | — | — | | Sandip Kapadia (28) | | 2025 | 429,167 | — | 234,475(29) | — | 438,667(30) | 28,459 | 1,130,768 | | | President, Reinsurance and Head of Actuarial, Skyward Specialty | 2024 | 400,000 | — | 190,711(31) | — | 262,520(32) | 6,291 | 859,522 |

  31. 2025 SUMMARY COMPENSATION TABLE

    (1) This column reflects each NEO’s principal position as of the date of this proxy statement. (2) Grant date fair value of stock awards in the form of restricted stock awards, RSUs and PSUs computed in accordance with the stock-based compensation accounting rules set forth in ASC 718. For performance awards linked to performance vesting criteria, the grant date fair value was calculated based on the probable outcome of the performance condition as of the grant date. Further details can be found in Note 18, "Summary of Significant Accounting Policies — Stock-Based Compensation" in our audited consolidated financial statements included in our Annual Report on Form 10-K filed with the SEC for the applicable year. The values reported for our NEOs 2023 stock awards have been updated to reflect the grant date fair value in accordance with ASC 718. (3) Grant date fair value of stock options computed in accordance with the stock-based compensation accounting rules set forth in ASC 718. Further details can be found in Note 18, "Summary of Significant Accounting Policies — Stock-Based Compensation" in our audited consolidated financial statements included in our Annual Report on Form 10-K filed with the SEC for the applicable year. (4) Consists of the grant date value of stock options under the 2022 Long-Term Incentive Plan granted during fiscal year ended December 31, 2023. (5) Consists of Company matching 401(k) contributions and 401(k) true-up for 2024 but paid in 2025 in the following amounts: $17,250 for Mr. Robinson, $13,500 for Mr. Haushill, $13,708 for Mr. Burkhart, and $10,959 for Mr. Kapadia. (6) Consists of the aggregate grant date value of RSU and PSU awards under the 2022 Long-Term Incentive Plan granted during fiscal year ended December 31, 2025 consisting of RSUs with a grant date value of $521,039 and PSU awards with a target grant date value totaling $1,042,078. The grant date value of these PSUs assuming attainment of the maximum performance levels totals $1,563,117. (7) Consists of the performance bonus earned by Mr. Robinson for the fiscal year ended December 31, 2025 in the amount of $2,625,000, and paid in March 2026, and a cash payment in the amount of $348,000, pursuant to the 2025 vesting of PCUs awarded to Mr. Robinson for the 2022–2024 performance period. (8) Consists of the aggregate grant date value of RSU and PSU awards under the 2022 Long-Term Incentive Plan granted during fiscal year ended December 31, 2024 consisting of RSUs with a grant date value of $544,956 and PSU awards with a target grant date value totaling $1,089,913. The grant date value of these PSUs assuming attainment of the maximum performance levels totals $1,634,833. (9) Consists of the performance bonus earned by Mr. Robinson for the fiscal year ended December 31, 2024 in the amount of $1,575,000, and paid in March 2025, and a cash payment in the amount of $532,000, pursuant to the 2024 vesting of PCUs awarded to Mr. Robinson for the 2021–2023 performance period. (10) Consists of the aggregate grant date value of RSU and PSU awards under the 2022 Long-Term Incentive Plan granted during fiscal year ended December 31, 2023 consisting of RSUs with a grant date value of $3,292,414 and PSU awards with a target grant date value totaling $584,829. The grant date value of these PSUs assuming attainment of the maximum performance levels totals $877,262. (11) Consists of the performance bonus earned for the fiscal year ended December 31, 2023 that was paid in March 2024. (12) Consists of the aggregate grant date value of RSU and PSU awards under the 2022 Long-Term Incentive Plan granted during fiscal year ended December 31, 2025 consisting of RSUs with a grant date value of $138,937, and PSU awards with a target grant date value totaling $277,874. The grant date value of these PSUs assuming attainment of the maximum performance levels totals $416,811. (13) Consists of the performance bonus earned by Mr. Haushill for the fiscal year ended December 31, 2025 in the amount of $600,000 and paid in March 2026 and a cash payment in the amount of $87,000, pursuant to the 2025 vesting of PCUs awarded to Mr. Haushill for the 2022–2024 performance period. (14) Consists of the aggregate grant date value of RSU and PSU awards under the 2022 Long-Term Incentive Plan granted during fiscal year ended December 31, 2024 consisting of RSUs with a grant date value of $127,141, and PSU awards with a target grant date value totaling $254,281. The grant date value of these PSUs assuming attainment of the maximum performance levels totals $381,422. (15) Consists of the performance bonus earned by Mr. Haushill for the fiscal year ended December 31, 2024 in the amount of $450,000 and paid in March 2025 and a cash payment in the amount of $84,000, pursuant to the 2024 vesting of PCUs awarded to Mr. Haushill for the 2021–2023 performance period. (16) Consists of the aggregate grant date value of RSU and PSU awards under the 2022 Long-Term Incentive Plan granted during fiscal year ended December 31, 2023 consisting of RSUs with a grant date value of $472,989 and PSU awards with a target grant date value totaling $146,179. The grant date value of these PSUs assuming attainment of the maximum performance levels totals $219,287. (17) Consists of the aggregate grant date value of RSU and PSU awards under the 2022 Long-Term Incentive Plan granted during fiscal year ended December 31, 2025 consisting of RSUs with a grant date value of $138,937, and PSU awards with a target grant date value totaling $277,874. The grant date value of these PSUs assuming attainment of the maximum performance levels totals $416,811. (18) Consists of the performance bonus earned by Mr. Burkhart for the fiscal year ended December 31, 2025 in the amount of $750,000 and paid in March 2026 and a cash payment in the amount of $77,333, pursuant to the 2025 vesting of PCUs awarded to Mr. Burkhart for the 2022–2024 performance period. (19) Consists of the aggregate grant date value of RSU and PSU awards under the 2022 Long-Term Incentive Plan granted during fiscal year ended December 31, 2024 consisting of RSUs with a grant date value of $127,141, and PSU awards with a target grant date value totaling $254,281. The grant date value of these PSUs assuming attainment of the maximum performance levels totals $381,422. (20) Consists of the performance bonus earned for the fiscal year ended December 31, 2024 paid in March 2025. (21) Consists of a one-time discretionary cash bonus of $21,000 paid to Mr. Burkhart to make him economically whole for the number of PSUs for the 2021-2023 performance period which were not eligible to vest due to an LPT charge, as the Committee determined that the NEOs should not be penalized for the LPT charge. (22) Consists of the aggregate grant date value of RSU and PSU awards under the 2022 Long-Term Incentive Plan granted during fiscal year ended December 31, 2023 consisting of RSUs with a grant date value of $469,747 and PSU awards with a target grant date value totaling $139,693. The grant date value of these PSUs assuming attainment of the maximum performance levels totals $209,559. (23) Consists of the performance bonus earned by Mr. Burkhart for the fiscal year ended December 31, 2023 in the amount of $350,000 and paid in March 2024, and a cash payment in the amount of $100,000, earned pursuant to the 2024 vesting of Long-Term Cash awarded to Mr. Burkhart during 2022 for the 2022-2024 performance period. (24) Ms. Ryan became an NEO in 2025. (25) Consists of a one-time discretionary sign-on bonus that was paid in March of 2025 when Ms. Ryan joined the Company.

  32. 2025 SUMMARY COMPENSATION TABLE

    (26) Consists of the aggregate grant date value of RSU and PSU awards under the 2022 Long-Term Incentive Plan granted during fiscal year ended December 31, 2025 consisting of RSUs with a grant date value of $61,685, and PSU awards with a target grant date value totaling $123,371. The grant date value of these PSUs assuming attainment of the maximum performance levels totals $185,056. (27) Consists of the performance bonus earned by Ms. Ryan for the fiscal year ended December 31, 2025 that was paid in March 2026. (28) Mr. Kapadia became an NEO in 2024. (29) Consists of the aggregate grant date value of RSU and PSU awards under the 2022 Long-Term Incentive Plan granted during fiscal year ended December 31, 2025 consisting of RSUs with a grant date value of $78,158, and PSU awards with a target grant date value totaling $156,317. The grant date value of these PSUs assuming attainment of the maximum performance levels totals $234,475. (30) Consists of the performance bonus earned by Mr. Kapadia for the fiscal year ended December 31, 2025 in the amount of $400,000 and paid in March 2026 and a cash payment in the amount of $38,667, pursuant to the 2025 vesting of PCUs awarded to Mr. Kapadia for the 2022–2024 performance period. (31) Consists of the aggregate grant date value of RSU and PSU awards consisting of RSUs with a grant date value of $63,570, and PSU awards with a target grant date value totaling $127,141. The grant date value of these PSUs assuming attainment of the maximum performance levels totals $190,675. (32) Consists of the performance bonus earned for the fiscal year ended December 31, 2024 in the amount of $225,000 and a cash payment in the amount of $37,520, earned pursuant to the 2024 vesting of PCUs awarded to Mr. Kapadia for the 2021–2023 performance period.

  33. GRANTS OF PLAN-BASED AWARDS FOR FISCAL YEAR ENDED DECEMBER 31, 2025

    GRANTS OF PLAN-BASED AWARDS FOR FISCAL YEAR ENDED DECEMBER 31, 2025 The following table presents information concerning grants of annual incentive compensation and equity awards to each of the NEOs during 2025. See the “Compensation Discussion and Analysis” section for detailed information regarding our STIP and RSU and PSU awards set forth in the table below.

  34. GRANTS OF PLAN-BASED AWARDS FOR FISCAL YEAR ENDED DECEMBER 31, 2025

    | | | | Estimated Future Payouts Under Non-Equity Incentive Plan Awards(1) | | | Estimated Future Payouts Under Equity Incentive Plan Awards(2) | | | All Other Stock Awards: Number of Shares of Stock or Units (#)(3) | Grant Date Fair Value of Stock and Option Awards ($)(4) | | Name | Award Type | Grant Date | Threshold ($) | Target ($) | Maximum ($) | Threshold (#) | Target (#) | Maximum (#) | | | | Andrew Robinson | STIP | | — | 1,500,000 | 2,250,000 | | | | | | | | RSU | 2/25/2025 | | | | | | | 10,133 | 521,039 | | | PSU | 2/25/2025 | | | | 5,067 | 20,266 | 30,398 | | 1,042,078 | | Mark Haushill | STIP | | — | 400,000 | 600,000 | | | | | | | | RSU | 2/25/2025 | | | | | | | 2,702 | 138,937 | | | PSU | 2/25/2025 | | | | 1,351 | 5,404 | 8,106 | | 277,874 | | John Burkhart | STIP | | — | 400,000 | 600,000 | | | | | | | | RSU | 2/25/2025 | | | | | | | 2,702 | 138,937 | | | PSU | 2/25/2025 | | | | 1,351 | 5,404 | 8,106 | | 277,874 | | Patricia Ryan | STIP | | — | 187,500 | 281,250 | | | | | | | | RSU | 5/7/2025 | | | | | | | 1,048 | 61,685 | | | PSU | 5/7/2025 | | | | 524 | 2,096 | 3,144 | | 123,371 | | Sandip Kapadia | STIP | | — | 292,500 | 438,750 | | | | | | | | RSU | 2/25/2025 | | | | | | | 1,520 | 78,158 | | | PSU | 2/25/2025 | | | | 760 | 3,040 | 4,560 | | 156,317 |

  35. GRANTS OF PLAN-BASED AWARDS FOR FISCAL YEAR ENDED DECEMBER 31, 2025

    (1) Represents annual incentive bonus opportunities under the STIP for each of the NEOs. See “Components of Our Executive Compensation Program" beginning on page 39. Actual bonus payments for 2025 are listed under Non-Equity Incentive Plan Compensation in the 2025 Summary Compensation Table on page 46. The target amounts reflect the dollar amount that would be payable if each performance goal is achieved at the target goal (i.e., 100 % of target) level. The Company STIP performance factor is capped at 150% of targeted awards with NEOs generally receiving 0% to 150%; the Compensation Committee retains discretion to recognize extraordinary achievement. There is no threshold level for STIP awards. (2) Represents the PSUs granted under the LTIP to each of the NEOs, which vest based on the Company’s performance with respect to the internal CR and a GBVPS metric (measured over the 2025-2027 performance period). The PSUs are eligible to vest on December 31, 2027, subject to continued service through such date and meeting certain predetermined performance goals. The maximum number of PSUs that may vest is capped at 150% of the target number of PSUs. If the threshold performance rule is not met, no PSUs are eligible to vest. Half of the 2025 PSUs are eligible to vest subject to the level of attainment of a three-year internal CR performance goal, with the number of PSUs eligible to vest determined based on our level of attainment of our internal CR performance goal during the three-year performance period ending December 31, 2027. The remaining half of the PSUs are eligible to vest subject to the level of attainment of our GBVPS performance goal as determined based on the level of performance reported in our Company’s year-end GAAP financial statements, as determined by the Committee, and relative to that of a peer group of comparison companies during the three-year performance period ending December 31, 2027. In certain cases, the PSU awards are also eligible to vest earlier upon a qualifying termination of employment, as described in more detail below. (3) Represents RSUs granted under the LTIP to each of the NEOs, which are scheduled to vest on January 1, 2028, subject to the NEO’s continued employment through the applicable vesting date. (4) Grant date fair value of stock awards in the form of RSUs and PSUs computed in accordance with the stock-based compensation accounting rules set forth in ASC 718. For performance awards linked to performance vesting criteria, the grant date fair value was calculated based on the probable outcome of the performance condition as of the grant date. Further details can be found in Note 18, "Stock Based Compensation" in our audited consolidated financial statements included in our Annual Report on Form 10-K filed with the SEC for the year ended December 31, 2025.

  36. OUTSTANDING EQUITY AWARDS AT FISCAL YEAR-END FOR FISCAL YEAR ENDED DECEMBER 31, 2025

    OUTSTANDING EQUITY AWARDS AT FISCAL YEAR-END FOR FISCAL YEAR ENDED DECEMBER 31, 2025 The following table summarizes the number of shares of our Common Stock underlying outstanding equity incentive plan awards for each of the NEOs as of December 31, 2025.

  37. OUTSTANDING EQUITY AWARDS AT FISCAL YEAR-END FOR FISCAL YEAR ENDED DECEMBER 31, 2025

    | | | Stock Options | | | Stock Awards | | | | | Name and Principal Position(1) | Grant Date(2) | Number of Securities Underlying Unexercised Options Unexercisable (#) | Option Exercise Price ($) | Option Expiration Date | Number of Shares or Units of Stock That Have Not Vested (#) | Market Value of Shares or Units of Stock That Have Not Vested ($)(3) | Equity Incentive Plan Awards: Number of Unearned Shares, Units or Other Rights That Have Not Vested (#) | Equity Incentive Plan Awards: Market or Payout Value of Unearned Shares, Units or Other Rights That Have Not Vested ($)(3) | | Andrew Robinson Chairman and Chief Executive Officer, Skyward Group | 02/25/2025 | | | | 10,133(4) | 517,898 | | | | | 02/25/2025 | | | | | | 20,266(5) | 1,035,795 | | | 02/27/2024 | | | | 14,959(6) | 764,554 | | | | | 02/27/2024 | | | | | | 29,918(7) | 1,529,109 | | | 02/27/2023 | | | | 15,151(8) | 774,368 | | | | | 02/27/2023 | | | | 17,575(9) | 898,258 | 15,151(10) | 774,368 | | | 01/12/2023 | | | | 50,000(11) | 2,555,500 | | | | | 01/12/2023 | | | | 100,000(12) | 5,111,000 | | | | | 01/12/2023 | 400,000(13) | 15.00 | 1/12/2033 | | | | | | Mark Haushill Chief Financial Officer, Skyward Group | 02/25/2025 | | | | 2,702(4) | 138,099 | | | | | 02/25/2025 | | | | | | 5,404(5) | 276,198 | | | 02/27/2024 | | | | 3,490(6) | 178,374 | | | | | 02/27/2024 | | | | | | 6,980(7) | 356,748 | | | 02/27/2023 | | | | 3,787(8) | 193,554 | | | | | 02/27/2023 | | | | 4,392(9) | 224,475 | 3,787(10) | 193,554 | | | 01/12/2023 | | | | 6,665(11) | 340,648 | | | | | 01/12/2023 | | | | 13,330(12) | 681,296 | | | | | 01/12/2023 | 53,330(13) | 15.00 | 1/12/2033 | | | | | | John Burkhart President, U.S. Property and Casualty, Skyward Specialty | 02/25/2025 | | | | 2,702(4) | 138,099 | | | | | 02/25/2025 | | | | | | 5,404(5) | 276,198 | | | 02/27/2024 | | | | 3,490(6) | 178,374 | | | | | 02/27/2024 | | | | | | 6,980(7) | 356,748 | | | 02/27/2023 | | | | 3,619(8) | 184,967 | | | | | 02/27/2023 | | | | 4,198(9) | | 3,619(10) | 184,967 | | | 01/12/2023 | | | | 6,665(11) | 340,648 | | | | | 01/12/2023 | | | | 13,330(12) | 681,296 | | | | | 01/12/2023 | 53,330(13) | 15.00 | 1/12/2033 | | | | |

  38. OUTSTANDING EQUITY AWARDS AT FISCAL YEAR-END FOR FISCAL YEAR ENDED DECEMBER 31, 2025

    | | | Stock Options | | | Stock Awards | | | | | Name and Principal Position(1) | Grant Date(2) | Number of Securities Underlying Unexercised Options Unexercisable (#) | Option Exercise Price ($) | Option Expiration Date | Number of Shares or Units of Stock That Have Not Vested (#) | Market Value of Shares or Units of Stock That Have Not Vested ($)(3) | Equity Incentive Plan Awards: Number of Unearned Shares, Units or Other Rights That Have Not Vested (#) | Equity Incentive Plan Awards: Market or Payout Value of Unearned Shares, Units or Other Rights That Have Not Vested ($)(3) | | Patricia Ryan Chief Legal Officer and Corporate Secretary, Skyward Group | 05/07/2025 | | | | 1,048(14) | 53,563 | | | | | 05/07/2025 | | | | | | 2,096(15) | 107,127 | | Sandip Kapadia President, Reinsurance and Head of Actuarial, Skyward Specialty | 02/25/2025 | | | | 1,520(4) | 77,687 | | | | | 02/25/2025 | | | | | | 3,040(5) | 155,374 | | | 02/27/2024 | | | | 1,745(6) | 89,187 | | | | | 02/27/2024 | | | | | | 3,490(7) | 178,374 | | | 02/27/2023 | | | | 2,020(8) | 103,242 | | | | | 02/27/2023 | | | | 2,343(9) | 119,751 | 2,020(10) | 103,242 | | | 01/12/2023 | | | | 5,000(11) | 255,550 | | | | | 01/12/2023 | | | | 10,000(12) | 511,100 | | | | | 01/12/2023 | 40,000(13) | 15.00 | 1/12/2033 | | | | |

  39. OUTSTANDING EQUITY AWARDS AT FISCAL YEAR-END FOR FISCAL YEAR ENDED DECEMBER 31, 2025

    (1)This column reflects each NEO’s principal position as of the date of this proxy statement. (2)All awards were granted pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long-Term Incentive Plan. (3)Market value is calculated using the closing price of our Common Stock as reported on the Nasdaq Global Select Market of $51.11 per share, on the last business day of 2025. (4)Amounts shown are RSUs granted on February 25, 2025. Upon vesting each unit is equivalent to one share of the Company’s Common Stock. These awards will fully vest on January 1, 2028, subject to continued services through such date. (5)Amounts shown represent the target award level for two separate PSU awards granted to our executives on February 25, 2025. Each PSU is equivalent to one share of the Company's Common Stock. The number of units eligible to vest under each award can range from 0% to 150% of the target award amount based on the satisfaction of specific performance target metrics during the requisite service period. These awards are eligible to vest subject to continued services through January 1, 2028 and the applicable level of attainment of the performance goals as determined by the Compensation Committee. These awards will fully vest on January 1, 2028. (6)Amounts shown are RSUs granted on February 27, 2024. Upon vesting each unit is equivalent to one share of the Company’s Common Stock. These awards will fully vest on January 1, 2027, subject to continued services through the vesting date. (7)Amounts shown represent the target award level for two separate PSU awards granted to our executives on February 27, 2024. Each PSU is equivalent to one share of the Company's Common Stock. The number of units eligible to vest under each award can range from 0% to 150% of the target award amount based on the satisfaction of specific performance target metrics during the requisite service period. These awards are eligible to vest subject to continued services through January 1, 2027 and the applicable level of attainment of the performance goals as determined by the Compensation Committee. These awards fully vest on January 1, 2027. (8)Amounts shown are RSUs granted on February 27, 2023. Upon vesting each unit is equivalent to one share of the Company’s Common Stock. These awards fully vested on January 1, 2026. (9)Amounts shown are PSUs granted on February 27, 2023 that settled at 116% of the target award levels with an internal CR of 90.9% for the three-year performance period ending December 31, 2025. These PSUs vested subject to continued service through the vesting date of December 31, 2025 and settled upon certification of the performance factor by the Compensation Committee which occurred on February 24, 2026. (10)Amounts shown are PSUs granted on February 27, 2023. Each PSU is equivalent to one share of the Company's Common Stock. The number of units eligible to vest under this award can range from 0% to 150% of the target award amount based on the level of satisfaction of performance condition targets during the requisite service period which is the three-year period ending on December 31, 2025. The actual performance level during the three-year performance period ending December 31, 2025 cannot be calculated until all the applicable peer publicly available Book Value per Share data for our peer group for 2025 is made publicly available, which is anticipated to occur sometime in May, 2026. After which, these awards will settle upon certification of the performance factor by the Compensation Committee. (11)Amounts shown are IPO RSUs granted on January 12, 2023. Upon vesting each unit is equivalent to one share of the Company’s Common Stock. Half of the RSUs vested on January 12, 2025 and the remaining 50% vested on January 12, 2026. (12)Amounts shown are IPO RSUs granted on January 12, 2023. Upon vesting each unit is equivalent to one share of the Company’s Common Stock. Half of the RSUs vested on January 12, 2026 and the remaining 50% will vest on January 12, 2027, subject to continued services through the vesting date. (13)Amounts shown are Non-Qualified Stock Options granted on January 12, 2023. Half of the options fully vested on January 12, 2026, and subject to continued service through the vesting date, the remaining 50% of the options will vest on January 12, 2027. (14)Amounts shown are RSUs granted on May 7, 2025. Upon vesting each unit is equivalent to one share of the Company’s Common Stock. This award will fully vest on January 1, 2028, subject to continued service through the vesting date. (15)Amounts shown represent the target award level for two separate PSU awards granted to the executive on May 7, 2025. Each PSU is equivalent to one share of the Company's Common Stock. The number of units eligible to vest under each award can range from 0% to 150% of the target award amount based on the satisfaction of specific performance target metrics during the requisite service period. These awards are eligible to vest subject to continued services through January 1, 2028 and the applicable level of attainment of the performance goals as determined by the Compensation Committee. These awards fully vest on January 1, 2028.

  40. OPTION EXERCISES AND STOCK VESTED FOR FISCAL YEAR ENDED DECEMBER 31, 2025

    OPTION EXERCISES AND STOCK VESTED FOR FISCAL YEAR ENDED DECEMBER 31, 2025 The following table sets forth certain information regarding stock vested during the year ended December 31, 2025 with respect to each of our NEOs. None of our NEOs exercised any options during 2025.

  41. OPTION EXERCISES AND STOCK VESTED FOR FISCAL YEAR ENDED DECEMBER 31, 2025

    | | | Stock Awards | | | | | Number of Shares Acquired on Vesting (#) | Value Realized on Vesting(1) ($) | | Andrew Robinson | 1/1/2025(2) | 22,796 | 1,152,110 | | | 3/6/2025(3) | 50,000 | 2,604,500 | | | 5/7/2025(4) | 33,282 | 1,958,979 | | Mark Haushill | 1/1/2025(2) | 5,699 | 288,027 | | | 3/6/2025(3) | 6,665 | 347,180 | | | 5/7/2025(4) | 8,320 | 489,715 | | John Burkhart | 1/1/2025(2) | 5,065 | 255,985 | | | 3/6/2025(3) | 6,665 | 347,180 | | | 3/6/2025(5) | 5,875 | 306,029 | | Patricia Ryan | — | — | — | | | — | — | — | | | — | — | — | | Sandip Kapadia | 1/1/2025(2) | 2,532 | 127,967 | | | 3/6/2025(3) | 5,000 | 260,450 | | | 3/6/2025(5) | 2,937 | 152,988 |

  42. OPTION EXERCISES AND STOCK VESTED FOR FISCAL YEAR ENDED DECEMBER 31, 2025

    (1) The value realized on vesting was calculated by multiplying the number of shares of SKWD Common Stock underlying awards that vested in 2025 by the closing price on the vesting date (or the previous trading day's closing price if the vesting date fell on a non-trading day) pursuant to the 2022 Long-Term Incentive Plan. (2) The closing price was $50.54 for the 2022 RSUs that vested for each of our NEOs on January 1, 2025 calculated using the previous trading day's closing price of SKWD stock for December 31, 2024. (3) The first tranche of the 2023 IPO RSUs vested and settled upon the closing price of the Company’s Common Stock on March 6, 2025 ($52.09 per share). (4) Messrs. Robinson and Haushill's 2022 PSU awards vested and settled upon the closing price of the Company’s Common Stock on May 7, 2025 ($58.86 per share) after certification by the Compensation Committee. (5) Messrs. Burkhart and Kapadia's 2022 PSU awards vested and settled upon the closing price of the Company’s Common Stock on March 6, 2025 ($52.09 per share) after certification by the Compensation Committee.

  43. POTENTIAL PAYMENTS UPON TERMINATION OR CHANGE IN CONTROL

    POTENTIAL PAYMENTS UPON TERMINATION OR CHANGE IN CONTROL We provide our NEOs with certain payments and benefits upon qualifying terminations of employment, provided specified requirements are met. For our Chief Executive Officer, these benefits are documented in his employment agreement, referred to as the Robinson agreement, and for our other executives, in their severance agreements and their individual equity award grants. We do not provide for any automatic single trigger vesting upon a change in control in our equity awards. The Robinson Agreement contains a 280G “best net” provision and overall we do not provide for any 280G excise tax gross-up payments to any of our executive officers. The Robinson Agreement, severance agreements with our other NEOs, and equity awards require the execution and non-revocation of a release of claims in order to receive severance benefits. The Employee Confidentiality and Non-Solicitation Agreement must be signed and agreed to as a condition of receiving an equity award(s) and the executive must continue to abide by the confidentiality and non-solicitation provisions agreed to therein. NEO Severance Agreements. Each of our executive officers has entered into an agreement with the Company that provides for certain payments and benefits upon such executive being terminated by the Company without “cause” or for “good reason” by the executive (as further described in the agreements), except for Mr. Robinson, whose potential severance is set forth in his employment agreement. The severance agreements provide a payment of twelve months of base salary and payment of COBRA premiums on behalf of the terminated executive for twelve months. Employment Agreement with Mr. Robinson. Pursuant to the Robinson Agreement, in the event that Mr. Robinson's employment with us is terminated by us without cause or if Mr. Robinson resigns for good reason, Mr. Robinson will be eligible to receive: •lump sum cash payment in an amount equal to his annual base salary as of the date of termination; •continued payment of group health benefit plan premiums for up to one year; •prorated target annual bonus for the year in which the termination occurs; •payment of any earned and accrued bonus for the calendar year proceeding the calendar year in which his employment is terminated; and •acceleration of any time-based vesting annual equity awards. If Mr. Robinson is terminated by us without cause or resigns for good reason within 12 months of a change in control he will receive the above payments, as well as accelerated vesting of any performance-based equity awards at not less than the target level, based on the valuation of the Board in good faith. Upon a termination due to death or disability, Mr. Robinson (or his beneficiary, as applicable) is entitled to a prorated target bonus for year of termination, any earned but unpaid bonus for the previously completed year, and acceleration of any time-based vesting equity awards. Pursuant to Mr. Robinson's employment agreement, “cause” generally means: •an act of dishonesty, fraud, theft, or embezzlement; •malfeasance or gross negligence in the performance of duties; •commission or conviction of or entry of a plea of guilty or nolo contendere with respect to any felony, or conviction of or entry of a plea of guilty or nolo contendere regarding any misdemeanor involving theft, defalcation, dishonesty or violence, or conviction related to any crime of moral turpitude; •willfully refusing or failure to perform duties and responsibilities, or failure to adhere to the directions of the Board or our or any of our subsidiaries' corporate codes, policies, or procedures; •the material breach of any of the covenants contained in the employment agreement; or •violation of any statutory, material contractual, or common law duty or obligation to us or any of our affiliates, including, without limitation, Mr. Robinson’s duty of loyalty; And “good reason” generally means the occurrence of any of the following events: •material diminution in salary, bonus opportunity, or annual equity opportunity; •material diminution in authority, duties, title, or responsibilities; •the involuntary relocation of principal place of employment that is not to a mutually-agreed location; •a material breach by us of any material provision of the employment agreement; or •removal of Mr. Robinson from the Board without cause pursuant to the Amended and Restated Shareholders' Agreement by and among the Shareholders party thereto and the Company dated as of March 12, 2014. Under his employment agreement, Mr. Robinson is subject to a 12 month non-compete provision, which is reduced to six months if his termination occurs within 12 months following a change in control or is due to disability; a non-solicitation of employees and customers covenant for one year, to run from the date of his termination; and standard ongoing confidentiality covenants. Termination Treatment Under Our Long-Term Incentive and Equity Awards. The long-term incentive and equity awards held by our NEOs provide for certain vesting treatment upon a termination of employment due to death, disability, a qualifying retirement, or a termination without cause or for good reason in connection with a change in control. The tables below reflect the grants made in 2023, 2024 and 2025 in accordance with disclosure rules. Specifically, the equity award agreements granted to the NEOs in 2023, 2024, and 2025 provide for full vesting upon a termination due to death or disability, with performance vesting awards eligible to vest based on actual performance for any completed annual measurement periods as of the date of termination and deemed attainment of the target performance levels for the then-ongoing measurement period. The 2023 restricted shares vested on January 1, 2026, and the 2023 performance-based awards vest upon certification of the performance results; all such awards are included as unvested and outstanding as of December 31, 2025 in accordance with the disclosure rules. In addition, the 2023, 2024, and 2025 equity awards are subject to pro-rated accelerated vesting (based on length of service) upon a qualifying retirement, as long as the retirement date is at least one year from the start of the performance or vesting period (or two years in the case of the 2023 awards granted in connection with our IPO). For performance-based awards, performance achievement is based on actual performance for any completed annual measurement periods as of the date of termination and the actual performance of the then-ongoing period, calculated at the conclusion of such annual measurement period. Generally, in order to be eligible for qualifying retirement treatment, our NEOs must meet the following criteria: (1) age 55 and five years of service; (2) provide advance written notice of at least 12 months; (3) assist the Company in succession planning and the transitioning of responsibilities through the scheduled retirement date; and (4) timely execute a waiver and release of claims. All of the equity and long-term incentive awards held by our NEOs include a double trigger, such that they will vest upon a qualifying termination of employment (generally without “cause,” for “good reason,” or due to “constructive termination,” each such term as defined in the award agreements) that occurs during a specified protection period related to a change in control (“CIC”) of the Company. The protection periods are as follows: •2023 stock options, 2023, 2024 and 2025 RSUs: immediately before and contingent upon or within 12 months following a CIC •2023 PSUs: immediately before and contingent upon a CIC, with payout based on actual performance for any completed measurement periods as of the termination date and target for the measurement period in which the CIC occurs

  44. POTENTIAL PAYMENTS UPON TERMINATION OR CHANGE IN CONTROL

    •2024 PSUs: after the commencement of a potential CIC and within the nine-month period immediately preceding the closing of such CIC, with payout based on actual performance •2025 PSUs: within 6 months immediately before and contingent upon or within 12 months following a CIC, with payout based on average actual performance for any completed measurement periods as of the termination date and target for any measurement periods that is not completed prior to the termination date

  45. Calculation of Potential Payments

    Calculation of Potential Payments For each NEO, the following table sets forth quantitative estimates of the payments and benefits that would have become payable if such executive’s employment had been terminated for the designated reason on December 31, 2025. The value of equity compensation awards is based on the closing price of our stock on Nasdaq on December 31, 2025, the last trading day of 2025. The amounts below reflect potential payments pursuant to the employment or severance agreements for such NEOs as described above and their outstanding equity awards. As of December 31, 2025, only Messrs. Robinson and Haushill were eligible to terminate employment due to a qualifying retirement.

  46. Calculation of Potential Payments

    | Name | Type of Payment | Involuntary or Good Reason Termination Prior to CIC ($) | Involuntary or Good Reason Termination in Connection with CIC (S) | Retirement ($) | Death or Disability ($) | | Andrew Robinson | Cash Severance | 1,000,000 | 1,000,000 | — | — | | | Pro-Rated Target Bonus | 1,500,000 | 1,500,000 | — | 1,500,000(1) | | | Equity Awards Acceleration(2) | 2,056,820(3) | 28,782,271(4) | 4,219,780(5) | 28,782,271(4) | | | Health and Welfare Benefits | 26,845 | 26,845 | — | — | | | Total | 4,583,665 | 31,309,116 | 4,219,780 | 30,282,271 | | Mark Haushill | Cash Severance | 500,000 | 500,000 | — | — | | | Pro-Rated Target Bonus | — | — | — | — | | | Equity Awards Acceleration(2) | — | 4,605,075(4) | 1,029,514(5) | 4,605,075(4) | | | Health and Welfare Benefits | 26,845 | 26,845 | — | — | | | Total | 526,845 | 5,131,920 | 1,029,514 | 4,605,075 | | John Burkhart | Cash Severance | 500,000 | 500,000 | — | — | | | Pro-Rated Target Bonus | — | — | — | — | | | Equity Awards Acceleration(2) | — | 4,575,085(4) | — | 4,575,085(4) | | | Health and Welfare Benefits | 26,845 | 26,845 | — | — | | | Total | 526,845 | 5,101,930 | — | 4,575,085 | | Patricia Ryan | Cash Severance | 375,000 | 375,000 | — | — | | | Pro-Rated Target Bonus | — | — | — | — | | | Equity Awards Acceleration(2) | — | 173,081(4) | — | 173,081(4) | | | Health and Welfare Benefits | 11,728 | 11,728 | — | — | | | Total | 386,728 | 559,809 | — | 173,081 |

  47. Calculation of Potential Payments

    | Name | Type of Payment | Involuntary or Good Reason Termination Prior to CIC ($) | Involuntary or Good Reason Termination in Connection with CIC (S) | Retirement ($) | Death or Disability ($) | | Name | Type of Payment | Involuntary or Good Reason Termination Prior to CIC ($) | Involuntary or Good Reason Termination in Connection with CIC (S) | Retirement ($) | Death or Disability ($) | | Sandip Kapadia | Cash Severance | 450,000 | 450,000 | — | — | | | Pro-Rated Target Bonus | — | — | — | — | | | Equity Awards Acceleration(2) | — | 3,090,235(4) | — | 3,090,235(4) | | | Health and Welfare Benefits | 35,989 | 35,989 | — | — | | | Total | 485,989 | 3,576,224 | — | 3,090,235 |

  48. Calculation of Potential Payments

    (1) Represents the pro rata bonus for the year of death or disability based on the target bonus the executive was eligible to receive for that year. (2) Represents the market value as of December 31, 2025 of stock awards accelerated or continued in each scenario. For purposes of this disclosure, market value is determined using the December 31, 2025 closing price of SKWD of $51.11 per share. (3) Represents accelerated vesting of one hundred percent (100%) of all unvested time-based annual awards as of the termination date. (4) Represents accelerated vesting of one hundred percent (100%) of all stock option, RSU, and PSU awards, reflecting actual performance for completed performance periods and target performance for incomplete performance periods for the 2023-2025 awards and 2025-2027 awards and target performance for the 2024-2026 awards, as provided for in the individual award agreements. (5) Represents prorated vesting of 2023-2025 and 2024-2026 RSUs and PSU awards.

  49. CEO PAY RATIO

    CEO PAY RATIO SEC rules under the Dodd-Frank Act require disclosure of the ratio of our CEO’s annual total compensation to the annual total compensation of our median team member. We calculated this ratio in accordance with Item 402(u) of Regulation S-K. To identify the median team member for 2025, we evaluated all team members employed as of December 31, 2025, excluding the CEO. The population included full-time and part-time team members who were active on the measurement date. Team members were ranked using a consistently applied compensation measure based on payroll records that included base pay, overtime, compensation for paid absences, taxable bonuses or incentive compensation, and vested equity. Base pay for team members hired during the year was annualized based on their compensation rate as of the measurement date, while variable compensation was included only if actually paid during the year. For 2025, the annual compensation of our median team member was $135,000. We then calculated the median team member’s annual total compensation using the same methodology used to determine CEO compensation for the Summary Compensation Table. Our CEO’s 2025 compensation was $5,532,117, representing the total compensation reported for Mr. Robinson in the “2025 Summary Compensation Table.” Based on these amounts, the ratio of the annual total compensation of Mr. Robinson to the annual compensation of our median team member was 41 to 1. The assumptions and methodologies used in the calculation of our estimated pay ratio are specific to our Company and our team member population; therefore, our pay ratio may not be comparable to the pay ratios reported by other companies.

  50. PAY VERSUS PERFORMANCE

    PAY VERSUS PERFORMANCE In this section, we are including the required disclosure for pay versus performance as defined by the SEC for our principal executive officer ("PEO") and Non-PEO NEOs and Company performance for the fiscal years listed below.

  51. PAY VERSUS PERFORMANCE

    | Fiscal Year(1) | Summary Compensation Table Total for PEO Robinson, Andrew(2) | Compensation Actually Paid to PEO Robinson, Andrew(3)(4) | Average Summary Compensation Table Total for non-PEO NEOs(2) | Average Compensation Actually Paid to non-PEO NEOs(5)(6) | SKWD Total Shareholder Return(7) | Peer Group Total Shareholder Return(7) | Net Income ($M) | Internal Combined Ratio(8) | | 2025 | $5,532,117 | $6,101,366 | $1,423,518 | $1,512,514 | $267.59 | $127.60 | $170.03 | 89.6% | | 2024 | $4,641,869 | $17,050,183 | $1,107,150 | $2,842,640 | $264.61 | $128.30 | $118.83 | 91.6% | | 2023 | $8,621,743 | $23,150,543 | $1,746,147 | $3,838,066 | $177.38 | $103.37 | $85.98 | 91.6% |

  52. PAY VERSUS PERFORMANCE

    (1) Mr. Robinson was our PEO for each fiscal year included in the table. The following officers are included in the Non-PEO NEO group for the following fiscal years: Year Non-PEO NEOs 2025 Mark Haushill, John Burkhart, Patricia Ryan, and Sandip Kapadia 2024 Mark Haushill, John Burkhart, Kirby Hill, and Sandip Kapadia 2023 Mark Haushill, John Burkhart, and Kirby Hill (2) Reflects compensation amounts reported in the “Total” column of the Summary Compensation Table (“SCT”) for the CEO and the average of the compensation amounts reported in the "Total" column of the SCT for the Non-PEO NEOs. (3) Amounts reflect the amounts reported in the “Summary Compensation Table Total for PEO” column adjusted as set forth in the table below, as determined in accordance with SEC rules. Amounts do not reflect the actual amount of compensation earned by or paid to our PEO during the applicable year. For information regarding the decisions made by the Compensation Committee with respect to the PEO’s compensation for fiscal year 2025, please see the Compensation Discussion and Analysis sections of this Proxy Statement. The PEO Summary Compensation Table to CAP reconciliation is summarized in the following table:

  53. PAY VERSUS PERFORMANCE

    | | PEO: Robinson, Andrew | | Prior FYE | 12/31/2024 | | Current FYE | 12/31/2025 | | Fiscal Year | 2025 | | SCT Total | $5,532,117 | | - Grant Date Fair Value of Option Awards and Stock Awards Granted in Fiscal Year | ($1,563,117) | | + Fair Value at Fiscal Year-End of Outstanding and Unvested Option Awards and Stock Awards Granted in Fiscal Year | $1,740,136 | | + Change in Fair Value of Outstanding and Unvested Option Awards and Stock Awards Granted in Prior Fiscal Years | $516,831 | | + Fair Value at Vesting of Option Awards and Stock Awards Granted in Fiscal Year That Vested During Fiscal Year | $0 | | + Change in Fair Value as of Vesting Date of Option Awards and Stock Awards Granted in Prior Fiscal Years For Which Applicable Vesting Conditions Were Satisfied During Fiscal Year | ($124,602) | | - Fair Value as of Prior Fiscal Year-End of Option Awards and Stock Awards Granted in Prior Fiscal Years That Failed to Meet Applicable Vesting Conditions During Fiscal Year | $0 | | Compensation Actually Paid | $6,101,366 |

  54. PAY VERSUS PERFORMANCE

    (4) For the PEO in the table above, the foregoing amounts were added and deducted to the Summary Compensation Table (“SCT”) amount to determine the compensation actually paid (“CAP”) as determined in accordance with SEC regulations. “Compensation actually paid” does not necessarily represent cash, and/or equity value transferred to the PEO without restriction, but rather is a value calculated under applicable SEC rules. Fair values set forth in the table below are computed in accordance with ASC 718 as of the end of the respective fiscal year, other than fair values of the awards that vest in the covered year, which are valued as of the applicable vesting date. The valuation methods and underlying assumptions did not materially differ from those disclosed at the time of grant date of the equity awards. (5) Amounts reflect the amounts reported in the “Average Summary Compensation Table Total for Non-PEO NEOs” column adjusted as set forth in the table below, as determined in accordance with SEC rules. Amounts do not reflect the actual amount of compensation earned by or paid to our Non-PEO NEOs during the applicable year. For information regarding the decisions made by the Compensation Committee in regards to the Non-PEO NEOs compensation for fiscal year 2025, please see the Compensation Discussion and Analysis sections of this Proxy Statement.

  55. PAY VERSUS PERFORMANCE

    | Prior FYE | 12/31/2024 | | Current FYE | 12/31/2025 | | Fiscal Year | 2025 | | SCT Total | $1,423,518 | | - Grant Date Fair Value of Option Awards and Stock Awards Granted in Fiscal Year | ($313,288) | | + Fair Value at Fiscal Year-End of Outstanding and Unvested Option Awards and Stock Awards Granted in Fiscal Year | $342,257 | | + Change in Fair Value of Outstanding and Unvested Option Awards and Stock Awards Granted in Prior Fiscal Years | $79,526 | | + Fair Value at Vesting of Option Awards and Stock Awards Granted in Fiscal Year That Vested During Fiscal Year | $0 | | + Change in Fair Value as of Vesting Date of Option Awards and Stock Awards Granted in Prior Fiscal Years For Which Applicable Vesting Conditions Were Satisfied During Fiscal Year | ($19,499) | | - Fair Value as of Prior Fiscal Year-End of Option Awards and Stock Awards Granted in Prior Fiscal Years That Failed to Meet Applicable Vesting Conditions During Fiscal Year | $0 | | Compensation Actually Paid | $1,512,514 |

  56. PAY VERSUS PERFORMANCE

    (6) For each of the NEOs in the table above, the foregoing amounts were added and deducted to the Summary Compensation Table (“SCT”) amount to determine the compensation actually paid (“CAP”) as determined in accordance with SEC regulations. “Compensation actually paid” does not necessarily represent cash, and/or equity value transferred to the applicable NEO without restriction, but rather is a value calculated under applicable SEC rules. Fair values set forth in the table below are computed in accordance with ASC 718 as of the end of the respective fiscal year, other than fair values of the awards that vest in the covered year, which are valued as of the applicable vesting date. The valuation methods and underlying assumptions did not materially differ from those disclosed at the time of grant date of the equity awards. (7) Total Shareholder Return ("TSR") is determined based on the value of an initial fixed investment of $100 made on January 13, 2023 (IPO Date). The TSR peer group consists of the NASDAQ Insurance Index TSR, which is used for our Stock Performance presentation set forth in the Company’s Annual Report on Form 10-K for the year ended December 31, 2025. (8) Our Company-Selected Measure, which is the measure that we believe represents the most important financial performance measure not otherwise presented in the table above that we use to link CAP to our NEOs for fiscal 2025 to our company’s performance is Internal Combined Ratio, which is consistent with the metric used for both our Short-Term incentive Plan and PSUs under our annual Long Term Incentive Program. See Appendix A - Non-GAAP Reconciliations on page A-1 at the end of this Proxy Statement for further information.

  57. Narrative to Pay Versus Performance Table

    Narrative to Pay Versus Performance Table For the fiscal year ending December 31, 2025, there are four important performance measures used to link compensation actually paid to our NEOs to company performance which are listed below in no particular order:

  58. Narrative to Pay Versus Performance Table

    | Measure | | Internal Combined Ratio | | Gross Written Premiums | | Growth in Book Value Per Share | | Absolute Stock Price |

  59. Analysis of the Information Presented in the Pay Versus Performance Table

    Analysis of the Information Presented in the Pay Versus Performance Table The following graph compares the compensation actually paid to our PEO, the average of the compensation actually paid to our remaining NEOs and the TSR performance of our stock price. The following graph compares the compensation actually paid to our PEO and the average of the compensation actually paid to our remaining NEOs with Net Income. The following graph compares the compensation actually paid to our PEO and the average of the compensation actually paid to our remaining NEOs as a result of our Internal Combined Ratio performance.

  60. DIRECTOR COMPENSATION

    DIRECTOR COMPENSATION

  61. 2025 Non-Employee Director Compensation Structure

    2025 Non-Employee Director Compensation Structure For fiscal year 2025, our non-employee directors were paid annual cash retainers for their Board service, as well as additional cash retainers for service as a committee chair. We also provide our non-employee directors with an annual equity grant of RSUs based on a fixed dollar value under the Company’s 2022 Long-Term Incentive Plan (the “2022 Plan”) that fully vests upon the first anniversary of the grant date. A summary of the 2025 non-employee director compensation is set forth below:

  62. 2025 Non-Employee Director Compensation Structure

    | Fiscal Year 2025 Director Compensation Program | | | Board Member Retainer | $75,000 | | Restricted Stock Unit Award(1) | $100,000 | | Leadership Retainers | | | –Lead Director | $25,000 | | –Audit Committee Chair | $20,000 | | –Compensation Committee Chair | $15,000 | | –Investment Committee Chair | $10,000 | | –Nominating and Corporate Governance Committee Chair | $10,000 | | –Risk Committee Chair | $10,000 |

  63. 2025 Non-Employee Director Compensation Structure

    (1) Our independent directors received an RSU award on May 7, 2025, with the number of units awarded calculated by dividing $100,000 by the grant price which was determined using the average closing price of SKWD Common Stock for each of the 5 trading days preceding the day of the Compensation Committee meeting. As such, the value reported in this table differs from the value reflected in the table below as below is calculated in accordance with SEC rules requiring grant date fair value to be determined pursuant to the accounting rules in ASC 718. Annual cash retainers are paid in quarterly installments in arrears and are prorated for any changes to committee service that occur during the year. Starting with the 2025 calendar year, directors may elect to defer the settlement of their RSU grants until one of three time periods – five years from the grant date, ten years from the grant date or until separation of Board service, provided the director informed the Company of their election to defer settlement of their 2025 award during fiscal year 2024. The deferred equity will automatically settle upon any separation of Board service or if there is a change of control (if earlier than the preselected settlement date), as further set out in the governing plan document. In the event a dividend is declared, dividend equivalent units will be added to a participant’s account, subject to the same vesting, forfeiture and settlement provisions as the underlying restricted stock units. Because these grants are for a fixed dollar amount, the number of shares of RSUs awarded annually to non-employee directors will vary, based on the price of our Common Stock on the grant date. New directors receive prorated grants at the time they join the Board. Any prorated grants will vest on the one-year anniversary of the director joining the Board. The short vesting time-frame mitigates director entrenchment, while the use of equity aligns the directors’ interests with those of our shareholders. We reimburse non-employee directors for out-of-pocket expenses incurred in connection with attending Board and committee meetings. We do not pay meeting attendance fees. The 2022 Plan provides that the sum of any cash compensation and the annual aggregate grant date fair value (computed as of the date of grant in accordance with applicable financial accounting rules) of all awards granted to any non-employee director during any single calendar year (for services as a director) may not exceed $750,000, subject to exceptions in extraordinary circumstances, provided that any director receiving any additional compensation may not participate in the decision regarding his or her compensation. Based on F.W. Cook’s review of market and benchmarking data for the Company’s 2025 director compensation program, the Board approved recommended updates to director compensation for fiscal year 2026, effective as of the 2026 Annual Meeting. The changes include increases to the annual cash and annual equity grant retainers, higher stipends for committee chairs, and an increase to the annual fee paid to the lead independent director. These updates are intended to better align total director compensation with the peer group median and to reflect the Company’s increased scope and scale following the Apollo acquisition.

  64. Director Compensation Table

    Director Compensation Table The following table sets forth information regarding the compensation of each of our non-employee directors who served during fiscal year 2025:

  65. Director Compensation Table

    | Director | Fees Earned or Paid in Cash(1) | Stock Awards(2) | All Other Compensation | Total | | Gena Ashe | $85,000(3) | $105,771 | — | $190,771 | | Robert Creager | $95,000(4) | $105,771 | — | $200,771 | | Marcia Dall | $90,000(5) | $105,771 | — | $195,771 | | James Hays | $75,000 | $105,771 | — | $180,771 | | Anthony J. Kuczinski | $107,500(6) | $105,771 | — | $205,771 | | Michael Morrissey | $82,500(7) | $105,771 | — | $190,771 | | Katharine Terry | $75,000 | $105,771 | — | $180,771 |

  66. Director Compensation Table

    (1) Reflects the aggregate dollar amount received for roles served during 2025 paid in quarterly installments on an annualized basis: (2) Grant date fair value computed in accordance with the stock-based compensation accounting rules set forth in ASC 718. For a more detailed description see Note 1 titled "Summary of Significant Accounting Policies — Earnings (loss) per share" to our audited consolidated financial statements included in our annual report on Form 10-K filed with the SEC. (3) Amount reflects annual retainer of $75,000 and an additional $10,000 for acting as Chair of the Nominating and Corporate Governance Committee. (4) Amount reflects annual retainer of $75,000 and an additional $20,000 for acting as Chair of the Audit Committee. (5) Amount reflects annual retainer of $75,000 and an additional $15,000 for acting as Chair of the Compensation Committee. (6) Amount reflects annual retainer of $75,000, an additional $25,000 for acting as Lead Independent Director, and an additional $7,500 for acting as Chair of the Risk Committee. (7) Amount reflects annual retainer of $75,000 and an additional $7,500 for acting as Chair of the Investment Committee.