DEF 14A of Skyward Specialty Insurance Group, Inc., Apr 1, 2024

DEF 14A of Skyward Specialty Insurance Group, Inc.

Filed Apr 1, 2024 · FY20230001519449-24-000015

Open on EDGAR

  1. Nominees for Director

    Nominees for Director 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. ("The Hanover"), an insurance company, where he rose to President of Specialty Insurance, Executive Vice President of Corporate Development and Chief Risk Officer. While at The 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 The 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, and PLNAR, an insurance technology company. Mr. Robinson previously served on the board of directors of Chaucer Plc, a Lloyd's of London managing agency. 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 since November 2022. Ms. Terry cofounded Surround Group, Inc. in June 2018 and serves as Chief Executive Officer. Surround is a national digital insurance agency that combines technology, design, and personalized advice for younger adults looking for a modern insurance experience. Ms. Terry also founded Kate Terry & Company, a management consulting firm focused on insurance product innovation. Prior to that, 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. Michael Morrissey has served on our Board 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.

  2. Continuing Directors

    Continuing Directors Gena Ashe has served on our Board 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 GXO Logistics (NYSE: GXO), a publicly traded, global logistics/supply chain outsourcing technology company, Cold Bore Capital Management Co., ALP LLC, a national commercial exterior services provider, and the Executive Leadership Council, a non-profit committed to opening channels of opportunity for Black executives to positively impact business and communities. Previously, Ms. Ashe served as a member of the Board of Directors of XPO Logistics (NYSE: XPO), a publicly traded, global supply chain solution provider, and as Vice Chairman of the Board of XPO Logistics, Europe SA (Euronext: XPO), a France based publicly traded transportation/logistics service provider. 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. Robert Creager has served on our Board since October 2012. From 2012 to 2022, Mr. Creager served as a Director and Chair of the Audit Committee of USA Truck, Inc., a public trucking and logistics company, which was acquired by DB Schenker in 2022. Previously he served as a Director and Chaired the Audit Committee of Mattress Firm, Inc., a mattress retailer, and GeoMet, Inc. (OTC: GMET), an energy company. From 1982 until 2009, Mr. Creager was an Assurance Partner with PricewaterhouseCoopers LLP. and was the leader of the Houston audit practice from 2001 to 2007. Mr. Creager holds a Bachelor of Science degree in Accounting from the University of Maryland. From 2010 to 2019, Mr. Creager was a board member of the National Association of Corporate Directors Texas TriCities Chapter, served as the Treasurer, and was a Governance Fellow. He has served on the boards of public, private, and not-for-profit companies. Mr. Creager is a senior financial professional with many years of public accounting experience, corporate governance experience as a director, and industry expertise. We believe Mr. Creager 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 his experience serving on Audit Committees. Marcia Dall has served on our Board since November 2022. Since October 2015, 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. 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. James Hays has served on our Board since April 2020. Since October 2018, Mr. Hays has served as Vice Chair and member of the Board of Directors of Brown & Brown, Inc., a public insurance brokerage company. Since August 1994, he served as the Founder and Chief Executive Officer of Hays Companies, an insurance broker that was acquired by Brown & Brown, Inc. in October 2018. At Hays Companies, Mr. Hays developed the organization into a nationwide leader in risk management, P&C, employee benefits, and personal lines insurance. As Chief Executive Officer of Hays Companies, Mr. Hays has overseen more than 25 years of growth, starting from a seven-person operation to a large-scale firm with more than 700 teammates in 30 offices. In addition to his leadership responsibilities, Mr. Hays maintains relationships with key accounts, helping customers understand their risk profile and developing robust insurance solutions. Mr. Hays holds a Bachelor of Science and a Master of Business Administration from the University of Minnesota. He currently serves on the boards of JS Held, LLC, a consulting firm, and Mid Country Acquisition Corp, a savings and loan holding company. We believe Mr. Hays is qualified to serve as a member of our Board based on his experience, qualifications, attributes, and skills including his extensive experience in multiple sectors of the insurance industry. Anthony J. Kuczinski has served on our Board since August 2023 and as Lead Independent Director since December 2023. 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 25 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.

  3. Director Compensation

    Director Compensation Non-independent directors do not receive compensation for their service on the Board. Independent directors, or their designees, received an annual retainer in the amount of $50,000 during 2023 for their service on the Board. The Chair of the Audit Committee receives an additional annual retainer of $20,000. The Chair of the Compensation Committee receives an additional annual retainer of $15,000. Effective February 2023, the Chair of the Nominating and Corporate Governance Committee receives an additional annual retainer of $10,000. Our independent directors, or their designees, are also eligible to receive grants of our common stock under the 2022 Plan that fully vest after the first anniversary of the grant date. The Board believes that it is important for independent directors of the Company to have a financial stake in the Company, such that the independent directors' interests align with those of the Company's shareholders. To meet this objective, the Board has established stock ownership guidelines for independent directors requiring a minimum equity holding of five times (5x) their annual base cash retainer. Independent directors will have five years to satisfy these guidelines after the date of adoption of these guidelines or the date of being designated as an independent director, whichever is later. We also have reimbursed our directors for expenses associated with attending meetings of our Board and its committees. The following table sets forth information regarding compensation earned by our non-employee directors during the year ended December 31, 2023.

  4. Director Compensation

    | Name | Fees Earned or Paid in Cash ($)(1) | Stock Awards ($)(2) | All Other Compensation ($) | Total ($) | | Gena Ashe(3) | $15,000(4) | $41,667(5) | — | $56,667 | | Robert Creager | $75,000(6) | $100,000 | — | $175,000 | | Marcia Dall | $53,750(7) | $100,000 | — | $153,750 | | James Hays | $50,000 | $100,000 | — | $150,000 | | Robert Kittel(8) | — | — | — | — | | Anthony J. Kuczinski(9) | $25,000(10) | $41,677(5) | — | $66,677 | | J. Cameron MacDonald(8) | — | — | — | — | | Michael Morrissey(11) | — | $25,000(5) | — | $25,000 | | Katharine Terry | $50,000 | $100,000 | — | $150,000 |

  5. Director Compensation

    ________________________ (1)Reflects the aggregate dollar amount of fees earned or paid in cash for services rendered for independent directors, including fees for service as a committee chair. (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 — Stock-Based Compensation" to our audited consolidated financial statements included in our annual report on Form 10-K filed with the SEC. (3)Ms. Ashe was appointed to the Board during the August 2023 Board meeting, taking effect immediately thereafter. (4)Amount reflects annual retainer of $50,000 paid pro-rata for 2023 Board service and an additional annual retainer of $10,000 paid pro-rata for acting as Chair of the Nominating and Corporate Governance Committee during August to December of 2023. (5)Amount reflects the pro-rata value of an annual Restricted Stock Award granted to independent directors for Board service during 2023 in accordance with our independent director compensation policy, and pursuant to the terms and conditions set forth in the Company’s 2022 Long-Term Incentive Plan. (6)Amount reflects annual retainer of $50,000, an additional $20,000 for acting as Chair of the Audit Committee and $5,000 for acting as Chair of the Nominating and Corporate Governance Committee from February to August, 2023. (7)Amount reflects annual retainer of $50,000 and an additional $3,750 for acting as Chair of the Compensation Committee from August to December, 2023. (8)Mr. Kittel and Mr. MacDonald resigned from the Board in November 2023. As non-independent directors, they did not receive any compensation for their board service. (9)Mr. Kuczinski was appointed to the Board just prior to the August 2023 Board meeting, and was appointed Lead Independent Director, effective December 2023. (10)Amount reflects annual retainer of $50,000 paid pro-rata for 2023 Board service during August to December of 2023. (11)Mr. Morrissey was appointed to the Board effective December 2023. PROPOSAL NO. 1:

  6. ELECTION OF CLASS II DIRECTORS

    ELECTION OF CLASS II 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 eight 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, three Class II directors will be elected for three-year terms. Based upon the recommendation of our Nominating and Corporate Governance Committee, our Board has nominated each of the director nominees set forth below to stand for election by our stockholders, in each case for a three-year term expiring at our 2027 annual meeting of stockholders or until his or her successor is duly elected and qualified.

  7. Nominees for Director

    Nominees for Director Our Nominating and Corporate Governance Committee has recommended, and our Board has approved, Andrew Robinson, Katharine Terry and Michael Morrissey as nominees for election as Class II directors at the Annual Meeting. If elected, Mr. Robinson, Ms. Terry and Mr. Morrissey will serve as Class II directors until the 2027 annual meeting of stockholders or until their 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 stockholder 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. Robinson, Ms. Terry and Mr. Morrissey. We expect that Mr. Robinson, Ms. Terry and Mr. Morrissey will accept such nomination; 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.

  8. 2023 Summary Compensation Table

    2023 Summary Compensation Table The following table sets forth the compensation received by our named executive officers for services rendered to us in such capacity for the years ended December 31, 2023 and 2022.

  9. 2023 Summary Compensation Table

    | Name and Principal Position | Year | Salary ($) | Stock Awards ($)(1) | Non-Equity Incentive Plan Compensation ($) | All other Compensation ($) | Total ($) | | Andrew Robinson Chief Executive Officer | 2023 | $800,000 | $900,000(2) | $2,132,000(3) | $16,500(4) | $3,848,500 | | | 2022 | $800,000 | $600,000(5) | $1,340,000(6) | $15,250(7) | $2,755,250 | | Mark Haushill Chief Financial Officer and Executive Vice President | 2023 | $450,000 | $225,000(8) | $444,000(9) | $16,500(4) | $1,135,500 | | | 2022 | $450,000 | $150,000(10) | $275,000(11) | $15,250(7) | $890,250 | | John Burkhart Executive Vice President and President of Specialty Lines | 2023 | $425,000 | $215,001(12) | $450,000(13) | $37,500(14) | $1,127,501 | | | 2022 | $400,000 | $133,334(15) | $356,667(16) | $15,250(7) | $905,251 | | Kirby Hill Executive Vice President and President of Industry Solutions, Captives and Programs | 2023 | $425,000 | $215,001(12) | $272,000(17) | $39,500(18) | $951,501 | | | 2022 | $425,000 | $143,334(19) | $231,667(20) | $15,250(7) | $815,251 |

  10. 2023 Summary Compensation Table

    ________________________ (1)Grant date fair value computed in accordance with the stock-based compensation accounting rules set forth in ASC 718. For performance awards linked to market performance 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 1, "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. (2)Consists of the aggregate value of Long-Term Awards under the 2022 Long Term Incentive Plan granted during fiscal year ended December 31, 2023. The value of the Restricted Stock Units ("RSUs") equals $300,000 and upon vesting each unit is equivalent to one share of the Company's common stock. This award fully vests on January 1, 2026. The value of two separate Performance Stock Unit ("PSU") awards, totaling $600,000, with vesting terms subject to obtaining specified performance criteria from January 1, 2023 through December 31, 2025. Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under each PSU award can range from 0% to 150% of the target amount, so that the grant date value of these PSUs assuming attainment of the maximum performance levels totals $900,000. These awards fully vest on January 1, 2026. (3)Consists of the performance bonus earned and paid to Mr. Robinson for the fiscal year ended December 31, 2023 in the amount of $1,600,000, and a cash payment in the amount of $532,000, pursuant to the vesting of Performance Cash Units ("PCUs") awarded to Mr. Robinson during 2021 for the 2021–2023 performance period. (4)Consists of $16,500 of Company matched 401(k) contributions. (5)Consists of the aggregate value of Long-Term Awards under the 2020 Long Term Incentive Plan granted during fiscal year ended December 31, 2022. The value of the Restricted Stock Award equals $300,000 and each share is equivalent to one share of the Company's common stock. This award fully vests on January 1, 2025. The value of the PSU award equals $300,000 with vesting terms subject to obtaining specified performance criteria from January 1, 2022 through December 31, 2024. Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the target amount, so that the grant date value of the PSU award assuming attainment of the maximum performance levels totals $450,000. This award fully vests on January 1, 2025. (6)Consists of the performance bonus earned and paid to Mr. Robinson for the fiscal year ended December 31, 2022 totaling $1,040,000, and the value of the PCUs awarded to Mr. Robinson during 2022. The value of the PCU award equals $300,000. Each PCU is equivalent to $100 upon settlement based on the target level of achievement. The number of units subject to vest under this award can range from 0% to 150% of the target amount, so that the grant date value of the PCU award assuming attainment of the maximum performance levels totals $450,000. This award fully vests on January 1, 2025. (7)Consists of $15,250 of Company matched 401(k) contributions. (8)Consists of the aggregate value of Long-Term Awards under the 2022 Long Term Incentive Plan granted during fiscal year ended December 31, 2023. The value of the RSUs equals $75,000 and upon vesting each unit is equivalent to one share of the Company's common stock. This award fully vests on January 1, 2026. The value of two separate PSU awards, totaling $150,000, with vesting terms subject to obtaining specified performance criteria from January 1, 2023 through December 31, 2025. Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under each award can range from 0% to 150% of the target amount, so that the grant date value of the PSU awards assuming attainment of the maximum performance levels totals $225,000. These awards fully vest on January 1, 2026. (9)Consists of the performance bonus earned and paid to Mr. Haushill for the fiscal year ended December 31, 2023 in the amount of $360,000, and a cash payment in the amount of $84,000, pursuant to the vesting of Performance Cash Units awarded to Mr. Haushill during 2021 for the 2021–2023 performance period. (10)Consists of the aggregate value of Long-Term Awards granted under the 2020 Long Term Incentive Plan during fiscal year ended December 31, 2022. The value of the Restricted Stock Award equals $75,000 and each share is equivalent to one share of the Company's common stock. This award fully vests on January 1, 2025. The value of the PSU award equals $75,000 with vesting terms subject to obtaining specified performance criteria from January 1, 2022 through December 31, 2024. Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the target amount, so that the grant date value of the PSU award assuming attainment of the maximum performance level totals $112,500. This award fully vests on January 1, 2025. (11)Consists of the performance bonus earned and paid to Mr. Haushill for the fiscal year ended December 31, 2022 totaling $200,000, and the value of the PCUs awarded to Mr. Haushill during 2022. The value of the PCU award equals $75,000. Each PCU is equivalent to $100 upon settlement based on the target level of achievement. The number of units subject to vest under this award can range from 0% to 150% of the target amount, so that the grant date value of the PCU award assuming attainment of the maximum performance level totals $112,500. This award fully vests on January 1, 2025. (12)Consists of the aggregate value of Long-Term Awards under the 2022 Long Term Incentive Plan granted during fiscal year ended December 31, 2023. The value of the RSUs equals $71,667 and upon vesting each unit is equivalent to one share of the Company's common stock. This award fully vests on January 1, 2026. The value of two separate PSU awards, totaling $143,334, with vesting terms subject to obtaining specified performance criteria from January 1, 2023 through December 31, 2025. Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under each award can range from 0% to 150% of the target amounts, so that the grant date value of the PSU awards assuming attainment of the maximum performance level totals $215,001. These awards fully vest on January 1, 2026. (13)Consists of the performance bonus earned and paid to Mr. Burkhart for the fiscal year ended December 31, 2023 in the amount of $350,000 and a cash payment in the amount of $100,000, pursuant to the Long-Term Cash award granted to Mr. Burkhart in 2021. (14)Consists of $16,500 of Company matched 401(k) contributions, and a one-time discretionary cash payment adjustment approved by the Compensation Committee of the Board, in the amount of $21,000 paid to Mr. Burkhart for the 2021-2023 performance period. (15)Consists of the aggregate value of Long-Term Awards granted under the 2020 Long Term Incentive Plan during fiscal year ended December 31, 2022. The value of the Restricted Stock Award equals $66,667 and each share is equivalent to one share of the Company's common stock. This award fully vests on January 1, 2025. The value of the PSU award equals $66,667 with vesting terms subject to obtaining specified performance criteria from January 1, 2022 through December 31, 2024. Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the target amount, so that the grant date value of the PSU award assuming attainment of the maximum performance level totals $100,001. This award fully vests on January 1, 2025.

  11. 2023 Summary Compensation Table

    (16)Consists of the performance bonus earned and paid to Mr. Burkhart for the fiscal year ended December 31, 2022 totaling $290,000, and the value of the PCUs awarded to Mr. Burkhart during 2022. The value of the PCU award equals $66,667. Each PCU is equivalent to $100 upon settlement based on the target level of achievement. The number of units subject to vest under this award can range from 0% to 150% of the target amount, so that the grant date value of the PCU award assuming attainment of the maximum performance level totals $100,001. This award fully vests on January 1, 2025. (17)Consists of the performance bonus earned and paid to Mr. Hill for the fiscal year ended December 31, 2023 in the amount of $200,000 and a cash payment in the amount of $72,000, pursuant to the Long-Term Cash award granted to Mr. Hill in 2021. (18)Consists of $16,500 of Company matched 401(k) contributions, and a one-time discretionary cash payment adjustment approved by the Compensation Committee of the Board, in the amount of $23,000 paid to Mr. Hill for the 2021-2023 performance period. (19)Consists of the aggregate value of Long-Term Awards granted under the 2020 Long Term Incentive Plan during fiscal year ended December 31, 2022. The value of the Restricted Stock Award equals $71,667 and each share is equivalent to one share of the Company's common stock. This award fully vests on January 1, 2025. The value of the PSU award equals $71,667 with vesting terms subject to obtaining specified performance criteria from January 1, 2022 through December 31, 2024. Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the target amount, so that the grant date value of the PSU award assuming attainment of the maximum performance level totals $107,501. This award fully vests on January 1, 2025. (20)Consists of the performance bonus earned and paid to Mr. Hill for the fiscal year ended December 31, 2022 totaling $160,000, and the value of the PCUs awarded to Mr. Hill during 2022. The value of the PCU award equals $71,667. Each PCU is equivalent to $100 upon settlement based on the target level of achievement. The number of units subject to vest under this award can range from 0% to 150% of the target amount, so that the grant date value of the PCU award assuming attainment of the maximum performance level totals $107,501. This award fully vests on January 1, 2025.

  12. Outstanding Equity Awards at December 31, 2023

    Outstanding Equity Awards at December 31, 2023 The following table sets forth information regarding outstanding equity awards held by our named executive officers as of December 31, 2023(1).

  13. Outstanding Equity Awards at December 31, 2023

    | Name and Principal Position | Grant Date(2)(3) | Number of Shares or Units of Stock That Have Not Vested (#) | Market Value of Shares or Units of Stock That Have Not Vested (#) (4) | 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 | | Andrew Robinson Chief Executive Officer | 02/27/2023 | 15,151(5) | $513,316 | — | — | | | 02/27/2023 | — | — | 30,302(6) | $1,026,632 | | | 01/12/2023 | 100,000(7) | $3,388,000 | — | — | | | 01/12/2023 | 100,000(8) | $3,388,000 | — | — | | | 01/12/2023 | — | — | 400,000(9) | $13,552,000 | | | 01/01/2022 | 22,796(10) | $772,328 | — | — | | | 01/01/2022 | — | — | 22,796(11) | $772,328 | | Mark Haushill Chief Financial Officer and Executive Vice President | 02/27/2023 | 3,787(5) | $128,304 | — | — | | | 02/27/2023 | — | — | 7,574(6) | $256,607 | | | 01/12/2023 | 13,330(7) | $451,620 | — | — | | | 01/12/2023 | 13,330(8) | $451,620 | — | — | | | 01/12/2023 | — | — | 53,330(9) | $1,806,820 | | | 01/01/2022 | 5,699(10) | $193,082 | — | — | | | 01/01/2022 | — | — | 5,699(11) | $193,082 | | John Burkhart Executive Vice President and President of Specialty Lines | 02/27/2023 | 3,619(5) | $122,612 | — | — | | | 02/27/2023 | — | — | 7,238(6) | $245,223 | | | 01/12/2023 | 13,330(7) | $451,620 | — | — | | | 01/12/2023 | 13,330(8) | $451,620 | — | — | | | 01/12/2023 | — | — | 53,330(9) | $1,806,820 | | | 01/01/2022 | 5,065(10) | $171,602 | — | — | | | 01/01/2022 | — | — | 5,065(11) | $171,602 | | Kirby Hill Executive Vice President and President of Industry Solutions, Captives and Programs | 02/27/2023 | 3,619(5) | $122,612 | — | — | | | 02/27/2023 | — | — | 7,238(6) | $245,223 | | | 01/12/2023 | 13,330(7) | $451,620 | — | — | | | 01/12/2023 | 13,330(8) | $451,620 | — | — | | | 01/12/2023 | — | — | 53,330(9) | $1,806,820 | | | 01/01/2022 | 5,445(10) | $184,477 | — | — | | | 01/01/2022 | — | — | 5,445(11) | $184,477 |

  14. Outstanding Equity Awards at December 31, 2023

    ________________________ (1)Amounts reflected in the table above do not include Restricted Stock Units ("RSUs") and Performance Stock Units ("PSUs") granted to our executive officers on January 1, 2021, that fully vested on January 1, 2024 and converted to shares of the Company's common stock since they were based on performance periods which ended on December 31, 2023. These awards are included in the executive officers' holdings reflected in the "Beneficial Ownership of Securities of Principal Stockholders and Management" section of this proxy statement. (2)All January 2022 awards were granted pursuant to the 2020 Skyward Specialty Long-Term Incentive Plan. (3)All other awards were granted pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long-Term Incentive Plan. (4)Market value is calculated using the closing price of our common stock as reported on the Nasdaq Global Select Market of $33.88 per share, on the last business day of 2023. (5)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 will fully vest on January 1, 2026. (6)Amounts shown represent two separate PSU awards granted to our executives on February 27, 2023. Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under each award can range from 0% to 150% of the amount shown based on the satisfaction of specific performance target metrics during the requisite service period. These awards fully vest on January 1, 2026. (7)Amounts shown are RSUs granted on January 12, 2023. Upon vesting each unit is equivalent to one share of the Company’s common stock. Subject to continued service through the vesting date, 50% of the RSUs shall vest on January 12, 2025 and the remaining 50% will vest on January 12, 2026. (8)Amounts shown are RSUs granted on January 12, 2023. Upon vesting each unit is equivalent to one share of the Company’s common stock. Subject to continued service through the vesting date, 50% of the RSUs shall vest on January 12, 2026 and the remaining 50% will vest on January 12, 2027. (9)Amounts shown are Non-Qualified Stock Options (Right-to-Buy) granted on January 12, 2023. Subject to continued service through the vesting date, 50% of the options shall vest on January 12, 2026 and the remaining 50% will vest on January 12, 2027. (10) Amounts shown are Restricted Stock Awards granted on January 1, 2022. Each share is equivalent to one share of the Company's common stock. These awards will fully vest on January 1, 2025. (11)Amounts shown are PSUs granted on January 1, 2022. Each PSU is equivalent to one share of the Company's common stock. The number of units subject to vest under this award can range from 0% to 150% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on January 1, 2025.