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 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.
Skyward Specialty Insurance Group, Inc. reported insider stock sales by its Head of Actuarial, an officer of the company, on 12/12/2025. The officer sold 1,486 shares of common stock at $50.03 per share and 1,200 shares at $50.01 per share, leaving 14,289 and then 13,089 shares beneficially owned directly after the respective transactions.
The sales were effected under a Rule 10b5-1 trading plan adopted on September 8, 2025. The reported share balance also reflects the acquisition of 231 shares on June 1, 2025 and 197 shares on December 1, 2025 through the Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan "ESPP" for purchase periods from December 1, 2024 to May 31, 2025 and from June 1, 2025 to November 30, 2025.
Skyward Specialty Insurance Group, Inc. entered into a new unsecured revolving credit facility with a maximum principal amount of $150.0 million, increasing to $250.0 million on the closing date of its acquisition of Apollo Group Holdings Limited. The facility permits up to $30.0 million in letters of credit, rising to $50.0 million at that closing, and includes an uncommitted accordion feature of up to $50.0 million. Borrowings will bear interest at term SOFR plus 150–190 basis points or a base rate plus 50–90 basis points, with a fee of 0.20%–0.35% on undrawn amounts, and availability runs through November 12, 2030.
The agreement includes customary covenants on additional indebtedness above $10.0 million, shareholder distributions and financial tests on net worth, leverage, ratings and liquidity. Skyward and its non-insurance wholly owned subsidiaries guarantee the obligations under a separate guaranty agreement. In connection with this new facility, the company terminated its prior March 28, 2023 credit agreement and fully repaid all outstanding amounts under that facility.
Skyward Specialty Insurance Group (SKWD) elected Christopher Peirce as a Class III director, effective February 1, 2026. The Board intends to appoint Mr. Peirce as Chair of the Audit Committee after the filing of the Company’s Form 10-K for the fiscal year ended December 31, 2025.
The Board determined Mr. Peirce is independent under Nasdaq and Sarbanes‑Oxley rules. He will receive standard non‑employee director compensation and enter the Company’s indemnification agreement. Robert Creager, currently a director, Audit Committee Chair, and Nominating and Corporate Governance Committee member, informed the Board he will not stand for re‑election as a Class I director in 2026. The Company announced these changes via press release on November 11, 2025.
Skyward Specialty Insurance Group (SKWD) filed its Q3 2025 report, showing higher revenue and earnings. Total revenues were $382,526 thousand, up from $300,888 thousand a year ago, driven by net earned premiums of $351,797 thousand.
Net income rose to $45,901 thousand, with diluted EPS of $1.10, compared with $36,668 thousand and $0.89 last year. For the nine-month period, revenues reached $1,030,956 thousand and net income was $126,798 thousand, or $3.03 diluted EPS. Operating cash flow was $356,308 thousand for the nine months. Stockholders’ equity increased to $961,423 thousand, supported by an improvement in accumulated other comprehensive income to $9,539.
Investments totaled $2,233,788 thousand, including $1,805,218 thousand of available-for-sale fixed maturities. As of October 31, 2025, common shares outstanding were 40,487,365.
Skyward Specialty Insurance Group, Inc. furnished a press release announcing results for the quarter and fiscal period ended September 30, 2025, via a Form 8-K.
The release is attached as Exhibit 99.1 and, under General Instruction B.2, the information is furnished and not deemed filed under the Exchange Act, nor incorporated by reference except as specifically stated. The filing also includes a forward-looking statements disclaimer.