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. director reports no holdings. A Form 3 was filed for director Peirce Christopher Locke reporting initial beneficial ownership status as of 02/01/2026. The filing states that no securities of Skyward Specialty Insurance Group, Inc. are beneficially owned, and both non-derivative and derivative tables show no positions.
Skyward Specialty Insurance Group CPO Thomas N. Schmitt reported stock activity tied to previously granted restricted stock units. On January 12, 2026, 5,000 shares of common stock were issued upon settlement of a 2023 IPO 4-year RSU grant and another 5,000 shares were issued from a 2023 IPO 3-year RSU grant, both at an exercise price of $0. To satisfy tax withholding on these vestings, the issuer withheld 2,149 shares and 1,968 shares at a price of $46.10 per share, which the footnotes state was mandated by the company and not a discretionary sale by Schmitt. Following these transactions, Schmitt directly beneficially owned 17,363 shares of Skyward common stock, and 5,000 RSUs from the 4-year grant remain outstanding.
Skyward Specialty Insurance Group EVP & Chief Claims Officer Sean W. Duffy reported restricted stock unit vesting and related tax withholding transactions in company stock. On January 12, 2026, 5,000 shares of common stock were issued upon settlement of a 2023 IPO RSU grant and another 5,000 shares were issued from a separate 2023 IPO RSU grant, both at an exercise price of $0. To cover tax obligations tied to these RSU vestings, the issuer withheld 2,276 shares and 2,095 shares at a price of $46.10 per share, which the filing notes as mandated by the company rather than discretionary sales by Duffy. Following these transactions, Duffy directly beneficially owned 16,036 shares of Skyward Specialty Insurance Group common stock.
Skyward Specialty Insurance Group Head of Actuarial Sandip A. Kapadia reported equity award activity tied to restricted stock units. On January 12, 2026, 5,000 shares of common stock were issued upon settlement of a 2023 IPO 4-year RSU grant and another 5,000 shares were issued from a 2023 IPO 3-year RSU grant, with each RSU converting into one share of common stock at an exercise price of $0.
On the same date, the issuer withheld 1,985 shares and 1,808 shares of common stock, respectively, to satisfy tax withholding obligations, using a share value of $46.10 based on the closing price on the vesting date. After these transactions, Kapadia directly beneficially owned 15,545 shares of Skyward Specialty Insurance Group common stock. The filing states that the tax-related share withholding was mandated by the company and was not a discretionary sale.
Skyward Specialty Insurance Group, Inc. officer John A. Burkhart III, President, US P&C, reported equity transactions on January 12, 2026 related to restricted stock unit (RSU) awards. He settled a total of 13,330 RSUs into common stock, with 6,665 shares from a 4-year 2023 IPO RSU grant and 6,665 shares from a 3-year 2023 IPO RSU grant, each RSU converting into one share at an exercise price of $0. To cover tax withholding obligations on these vestings, the issuer withheld 2,798 shares and 2,623 shares of common stock at a price of $46.1 per share, as mandated under the company’s long-term incentive plan. After these transactions, Burkhart directly beneficially owned 32,271 shares of common stock.
Skyward Specialty Insurance Group Chairman and CEO Andrew S. Robinson reported the vesting and settlement of restricted stock units into common stock. On January 12, 2026, 100,000 RSUs from two 2023 IPO grants converted into 100,000 shares of common stock at an exercise price of $0. In connection with this vesting, a total of 39,532 shares were withheld by the company to cover tax obligations, using a share value of $46.10 on the vesting date. After these transactions, Robinson directly beneficially owned 134,915 shares of common stock. The 4-year IPO RSU grant shows 50,000 derivative RSUs remaining outstanding, while the 3-year IPO RSU grant is now fully settled.
Skyward Specialty Insurance Group’s reporting person, a director and Chairman & CEO, filed an amended insider trading report. The amendment explains that a prior Form 4 incorrectly showed the reported transactions as being made under a Rule 10b5-1 trading plan because that box was checked by mistake. The company states that all other details from that original filing remain correct. Following the reported transactions, the reporting person beneficially owns 74,447 shares of common stock directly.
Skyward Specialty Insurance Group Chief Information Officer Dan PK Bodnar reported vesting and settlement of restricted stock units and related tax withholding in company shares. On January 12, 2026, 5,000 common shares were issued upon settlement of a 2023 IPO 4-year RSU grant and another 5,000 shares were issued from a 2023 IPO 3-year RSU grant, each at an exercise price of $0. To satisfy tax obligations mandated by the company, 2,049 shares and 1,868 shares of common stock were withheld at a value of $46.10 per share based on the closing price on the vesting date. After these transactions, Bodnar directly held 24,998 shares of Skyward Specialty common stock. The RSU awards each originally covered 10,000 units, with vesting schedules tied to service through January 2025, 2026 and 2027.
Skyward Specialty Insurance Group EVP & CFO Mark W. Haushill reported the vesting and settlement of previously granted restricted stock units (RSUs) into common stock. On January 12, 2026, 6,665 shares were issued upon settlement of a 2023 IPO four-year RSU grant and another 6,665 shares were issued from a 2023 IPO three-year RSU grant, both at an exercise price of $0 per share. To cover tax withholding obligations tied to these vestings, the issuer withheld 2,797 shares and 2,623 shares at a price of $46.1 per share, transactions that were mandated by the company and not discretionary. Following these transactions, Haushill directly owned 133,456 shares of Skyward Specialty common stock.
Skyward Specialty Insurance Group, Inc. completed its acquisition of Apollo Group Holdings Limited, buying 100% of Apollo’s shares for approximately $555.0 million. The price included $371.0 million in cash and the issuance of 3,679,332 shares of Skyward common stock.
To help fund the cash portion and related costs, Skyward entered into an unsecured term loan credit agreement providing two delayed-draw facilities totaling $300.0 million, split equally between Tranche A and Tranche B. These loans bear interest at either term SOFR plus 150–190 basis points or a base rate plus 50–90 basis points, depending on the company’s debt-to-capitalization ratio, and mature in 2028 and 2029, respectively.
The facilities include customary covenants on additional indebtedness, capital returns, and financial metrics, and are guaranteed by certain non-insurance subsidiaries. Skyward also amended an existing credit agreement to allow pre-funding of revolving loans in connection with the Apollo acquisition, with detailed terms available in the referenced exhibits.