Welcome to our dedicated page for Skyward Specialty Insurance Group SEC filings (Ticker: SKWD), a comprehensive resource for investors and traders seeking official regulatory documents including 10-K annual reports, 10-Q quarterly earnings, 8-K material events, and insider trading forms.
Skyward Specialty Insurance Group, Inc. filings document formal disclosures for a specialty property and casualty insurance issuer with U.S. Skyward Specialty operations and Apollo Lloyd's platform operations. Recent 8-K reports furnish operating results, segment presentation, acquisition-related financial statements and pro forma combined information, and credit arrangements used in the company's capital structure.
Proxy and governance filings cover annual meeting matters, director elections, board committee changes, executive compensation, equity awards, employment agreements, severance provisions, indemnification arrangements, and related corporate-governance disclosures.
Skyward Specialty Insurance Group, Inc. Head of Actuarial Sandip A. Kapadia reported multiple equity compensation moves. He acquired common shares through the settlement of performance share units and received new grants of restricted stock units and additional performance share units under long-term incentive plans.
The new awards include 2,884 RSUs vesting on January 1, 2029, 2,884 PSUs that can vest between 0% and 200% of target and fully vest on December 31, 2028, and 4,326 RSUs vesting 50% on January 1, 2029 and 50% on January 1, 2030. Separately, 847 common shares were withheld at $45.89 per share to cover tax obligations, a disposition mandated by the company rather than a discretionary sale, leaving him with 17,041 common shares held directly.
Skyward Specialty Insurance Group Chief Information Officer Dan PK Bodnar reported multiple equity compensation transactions. On February 25, he acquired 2,343 shares of common stock through the exercise and settlement of 2,020 performance share units and received new equity awards, including 1,261 RSUs, 1,261 PSUs, and 4,326 additional RSUs under long-term incentive plans.
Footnotes explain that the 2023 PSUs vested based on performance criteria through December 31, 2025, and that the new 2026 RSU and PSU awards vest between December 31, 2028 and January 1, 2030, subject to continued service and performance conditions. On February 26, 876 shares of common stock were disposed of at $45.89 per share to cover tax withholding obligations required by the company, rather than a discretionary market sale. After these transactions, Bodnar directly owned 26,465 shares of common stock.
Skyward Specialty Insurance Group CPO Thomas N. Schmitt reported multiple equity award events and related tax withholding. He acquired common stock through settlement of previously granted performance share units (PSUs), and received new 2026 long-term incentive awards in the form of restricted stock units (RSUs) and PSUs, each covering 1,442 units at a stated price of $0.00 per unit.
To cover tax obligations from the PSU vesting and settlement, 1,153 shares of common stock were withheld at $45.89 per share in a disposition mandated by the issuer and not a discretionary sale. After these transactions, Schmitt directly owned 16,523 shares of common stock.
Skyward Specialty Insurance Group EVP & CFO Mark W. Haushill reported multiple equity compensation moves. He acquired 3,787 common shares through settlement of previously granted performance share units (PSUs), then had 1,436 shares withheld at $45.89 per share to cover tax obligations, leaving him with 136,412 directly held common shares.
On February 25, 2026, he also received new long-term incentive awards: 4,326 restricted stock units (RSUs) that are scheduled to vest on January 1, 2029, plus two PSU grants of 4,326 units each that can vest between 0% and 200% based on performance through December 31, 2028. A prior 3,787-PSU award for the 2023–2025 period fully vested on December 31, 2025 and settled after Compensation Committee certification.
Skyward Specialty Insurance Group EVP & Chief Claims Officer Sean W. Duffy reported equity award activity and a related tax-withholding share disposition. On February 25, 2026, 2,861 performance share units granted in 2023 fully vested after meeting performance criteria and were settled into an equal number of common shares. On the same date, he received new equity awards: 1,442 RSUs vesting on January 1, 2029, 1,442 PSUs that can vest from 0% to 200% of target and fully vest on December 31, 2028, and 4,326 RSUs with 50% vesting on January 1, 2029 and 50% on January 1, 2030. A related Form 4 entry shows 1,391 common shares were disposed of at $45.89 per share on February 26, 2026 to satisfy tax withholding obligations mandated by the company, not as a discretionary trade, leaving him with 17,963 common shares held directly.
Skyward Specialty Insurance Group, Inc. Chairman and CEO Andrew S. Robinson reported several equity compensation events involving the company’s common stock and long-term incentive plan awards. These are primarily grants, vesting, and tax withholding transactions rather than open-market purchases or sales.
On February 25, 2026, 15,151 Performance Share Units (PSUs) granted in 2023 fully vested after achieving specified performance criteria and were settled in an equal number of common shares. On the same date, Robinson received a new award of 28,841 Restricted Stock Units (RSUs), which are scheduled to vest on January 1, 2029, subject to continuous service. He was also granted 28,841 new PSUs that can vest between 0% and 200% of this amount based on performance targets through December 31, 2028. Separately, on February 26, 2026, 6,916 shares of common stock were withheld at a price of $45.89 per share to satisfy tax obligations tied to the PSU vesting, a disposition mandated by the issuer and not a discretionary sale.
Skyward Specialty Insurance Group President, US P&C, John A. Burkhart III reported equity award activity and related tax withholding. He settled 3,619 Performance Share Units into Common Stock, with 1,652 shares withheld at $45.89 per share to cover tax obligations in a non‑discretionary transaction mandated by the company, leaving 34,817 Common shares held directly.
Burkhart also received new long-term incentives: a grant of 7,210 Restricted Stock Units that vest 100% on January 1, 2029, and two separate grants of 7,210 Performance Share Units each that fully vest on December 31, 2028. The PSUs can ultimately vest between 0% and 200% of the target amount based on specified performance criteria.
Skyward Specialty Insurance Group, Inc. approved a new form of executive employment agreement to be used with its executive officers. The agreement sets each executive’s annual base salary and target bonus, which the board or its committees will review and may adjust at least once a year.
The company entered into this agreement with Chairman and CEO Andrew Robinson and President, U.S. Property and Casualty, John Burkhart. Mr. Robinson’s agreement, effective April 1, 2026, provides for a base salary of at least $1,100,000, a target bonus of 150% of base salary, and an annual long-term equity award with a grant date fair value of at least $4,000,000, subject to board discretion.
Mr. Burkhart’s agreement, effective January 1, 2026, provides for a base salary of at least $600,000, a target bonus equal to 100% of base salary, and an annual long-term equity award with a grant date fair value of at least $1,000,000, also subject to board discretion. The agreements include severance benefits if employment ends without cause or for good reason, potential bonus and equity vesting, COBRA premium reimbursement for up to 12 months, and non‑competition and non‑solicitation restrictions after employment ends.
Skyward Specialty Insurance Group reported a very strong fourth quarter and full-year 2025. Q4 2025 net income rose to $43.2 million, or $1.03 per diluted share, from $14.4 million, or $0.35, in Q4 2024. Full-year 2025 net income reached $170.0 million, or $4.07 per diluted share, up from $118.8 million, or $2.87, in 2024.
Gross written premiums were $439.5 million in Q4 2025, a 13.2% increase, and $2.17 billion for 2025, up 24.3%, driven by accident & health, specialty programs, surety, and agriculture and credit (re)insurance. The Q4 combined ratio improved to 88.5%, with an ex-cat combined ratio of 87.7%, and the full-year combined ratio improved to 89.3%.
Adjusted operating income was $48.9 million in Q4 2025, or $1.17 per diluted share, versus $33.2 million, or $0.80, a year earlier. For 2025, adjusted operating income was $167.4 million, or $4.00 per diluted share. Return on equity for the year was 18.9%, and book value per share increased to $24.92 at December 31, 2025, up 26% from December 31, 2024.
Reinhart Partners, LLC has disclosed a significant ownership stake in Skyward Specialty Insurance Group, Inc. As of the event date of 12/31/2025, Reinhart reports beneficial ownership of 2,416,753 shares of Skyward’s common stock, representing 5.97% of the outstanding class.
The firm has sole voting power over 2,217,570 shares and sole dispositive power over 2,416,753 shares, with no shared voting or dispositive authority. Reinhart states the shares were acquired and are held in the ordinary course of business and not for the purpose of changing or influencing control of Skyward.