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 delivered strong first-quarter 2026 growth, driven by its acquisition of Apollo Group Holdings. Net earned premiums rose to $434.0M from $300.4M, and gross written premiums increased to $667.7M from $535.3M.
Net income improved to $49.7M versus $42.1M, with diluted EPS at $1.09 compared with $1.01. The combined ratio edged down to 89.5% from 90.5%, reflecting solid underwriting performance.
The Apollo segment contributed $80.1M of revenue and $22.2M of net income after its $559.1M purchase, which included $371.1M cash and share consideration. Total assets expanded to $6.55B, with operating cash flow of $116.5M supporting higher investment and debt levels used to fund the acquisition.
Skyward Specialty Insurance Group, Inc. executive Thomas N. Schmitt reported compensation-related equity activity tied to performance share units. On May 6, 2026, he exercised derivative awards to acquire 3,358 shares of common stock and settled 2,525 performance share units (PSUs), each convertible into one share.
To cover tax withholding obligations from the PSU vesting and settlement, 1,322 shares were automatically withheld and disposed of, a transaction the company describes as mandated rather than discretionary. Following these transactions, Schmitt directly held 18,559 shares of common stock, and the PSU award granted in February 2023 is now fully vested and settled.
Skyward Specialty Insurance Group, Inc. reports that Head of Actuarial Sandip A. Kapadia settled a 2023 LTIP Performance Share Unit award on May 6, 2026. He exercised 2,020 PSUs granted on February 27, 2023, receiving 2,686 shares of Common Stock after the award fully vested based on performance through December 31, 2025.
In connection with this vesting, 1,374 shares were automatically withheld at $43.6800 per share to satisfy tax withholding obligations, a disposition mandated by the issuer and not discretionary. After these transactions, he directly owns 18,353 shares of Skyward Specialty common stock.
Skyward Specialty Insurance Group, Inc. Chief Information Officer Dan PK Bodnar reported the settlement of performance-based equity awards. On May 6, 2026, he acquired 2,686 shares of common stock upon settlement of Performance Share Units (PSUs) granted under the 2023 long-term incentive plan, following achievement of specified performance criteria through December 31, 2025.
In connection with this vesting and settlement, 1,004 shares were withheld to cover tax withholding obligations at a value of $43.68 per share. The filing states this tax-withholding disposition was mandated by the issuer and was not a discretionary transaction by Bodnar. After these transactions, he directly holds 28,147 shares of common stock.
Skyward Specialty Insurance Group, Inc. executive John A. Burkhart III, President US P&C, settled 3,619 Performance Share Units into Common Stock. In connection with this vesting, 1,894 shares were withheld at $43.68 per share to cover tax obligations. Following these compensation-related transactions, he directly holds 37,736 shares of Common Stock.
Skyward Specialty Insurance Group CFO Mark W. Haushill reported compensation-related share movements tied to performance awards. He exercised performance share units into 5,036 shares of Common Stock, with 1,982 shares withheld to satisfy tax obligations as mandated by the issuer. These tax-withholding dispositions were not open-market sales or discretionary trades. After the transactions, he directly holds 139,466 shares of Skyward Specialty Insurance Group, Inc. common stock.
Skyward Specialty Insurance Group Chairman & CEO Andrew S. Robinson settled a performance-based share award and had shares withheld for taxes. On May 6, 2026, he exercised 15,151 Performance Share Units (PSUs), each delivering one share of common stock upon settlement. In connection with this vesting, 7,930 shares of common stock were withheld at a price of $43.68 per share to satisfy tax withholding obligations, a disposition mandated by the company rather than a discretionary sale. Following these transactions, he holds 179,894 shares of common stock directly. The PSUs were originally granted on February 27, 2023 and vested based on performance criteria measured from January 1, 2023 through December 31, 2025, with settlement occurring after certification by the Compensation Committee.
Skyward Specialty Insurance Group EVP Sean W. Duffy reported equity compensation activity tied to performance share awards. On May 6, 2026, 2,861 Performance Share Units (PSUs) granted on February 27, 2023, fully vested based on performance from January 1, 2023 through December 31, 2025 and were settled in an equal number of common shares.
To cover related tax withholding obligations, 1,671 common shares were withheld, a disposition that the company mandated and that was not a discretionary market transaction. After these transactions, Duffy directly held 20,097 shares of Skyward Specialty Insurance Group common stock.
Terry Katharine reported acquisition or exercise transactions in this Form 4 filing.
Skyward Specialty Insurance Group, Inc. director Terry Katharine reported a new equity award. On May 6, 2026, she received a grant of 3,334 restricted stock units (RSUs), each representing one share of common stock after vesting and settlement.
The award will fully vest on the date of the company’s 2027 Annual Meeting of Shareholders, subject to the award terms. Katharine has elected to defer settlement of this RSU award until her separation from the company under the Deferred Compensation Plan for Non-Employee Directors. Following the reported transactions, she directly holds 6,780 shares of common stock.
Peirce Christopher Locke reported acquisition or exercise transactions in this Form 4 filing.
Skyward Specialty Insurance Group, Inc. director Christopher Locke received a grant of 3,890 restricted stock units (RSUs). Each RSU represents the right to receive one share of the company’s common stock after vesting and settlement.
The award was granted on May 6, 2026 and is scheduled to fully vest on the date of the company’s 2027 Annual Meeting of Shareholders, subject to the terms of the award agreement. Following the reported transactions, Locke holds 3,200 shares of common stock directly and 3,890 RSUs tied to common stock.