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. filed an amendment on Form 144/A reporting previously issued common stock related to compensatory stock bonuses. The filing lists two compensatory issuances: 5,781 shares dated 03/05/2025 and 2,616 shares dated 01/01/2025. The broker contact shown is Merrill Lynch, 800 Capitol Street, Houston, TX.
Skyward Specialty Insurance Group, Inc. director Anthony J. Kuczinski reported open-market purchases of a total of 2,000 shares of common stock on May 21, 2026, at prices of $47.00 and $47.20 per share, bringing his direct holdings to 15,977 shares.
Capital International Investors reported beneficial ownership of 831,378 shares of Skyward Specialty Insurance Group, Inc., representing 1.9% of the 44,543,065 shares believed outstanding as of 03/31/2026. The filing is an Amendment No. 1 to a Schedule 13G, and CII states sole voting and dispositive power over the reported shares.
Skyward Specialty Insurance Group director Gena L. Ashe reported RSU vesting and related share sales. On May 11, 2026, 1,797 Restricted Stock Units from a 2025 award converted into an equal number of common shares. To cover taxes and fees from this vesting, Ashe sold 740 common shares in open-market transactions at $46.35 per share. Following these transactions, Ashe directly holds 4,570 shares of common stock, reflecting a net increase in ownership from the RSU award.
Skyward Specialty Insurance, Inc. filed an amendment to a Form 144 disclosing the proposed sale of 1,797 shares of Common Stock on 05/11/2026. The shares are identified as a 2025 BOD RSU Award and the transaction is described as a Compensatory Payment. The filing lists Merrill Lynch at 800 Capitol Street, Houston, TX, and shows the securities will trade on the NYSE.
Skyward Specialty Insurance Group, Inc. held its Annual Meeting of Shareholders on May 5, 2026. Shareholders elected directors Peter C. Hearn and Gena Ashe, with Hearn receiving 34,790,416 votes for and Ashe receiving 25,679,644 votes for, along with broker non-votes in each case.
In a non-binding advisory vote, shareholders approved the compensation of the company’s named executive officers, with 33,368,427 votes for and 2,308,030 against. Shareholders also ratified Ernst & Young LLP as independent auditors for the fiscal year ending December 31, 2026, by a vote of 37,739,694 for, 289,410 against, and 22,346 abstentions.
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 19,881 shares of common stock, and the PSU award granted in February 2023 is now fully vested and settled.