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.
The Skyward Specialty Insurance Group, Inc. (Nasdaq: SKWD) SEC filings page on Stock Titan provides access to the company’s regulatory disclosures as a specialty commercial property and casualty insurer. As a Nasdaq Global Select Market registrant, Skyward Specialty files current and periodic reports with the U.S. Securities and Exchange Commission that describe its financial condition, capital structure, governance, and material events.
Investors can review Form 8-K filings for information on material definitive agreements, credit facilities, acquisitions, and governance developments. For example, recent 8-K filings describe a new unsecured revolving credit agreement with specified covenants and an accordion feature, the termination of a prior credit agreement, and share purchase agreements related to the acquisition of Apollo Group Holdings Limited. Other 8-Ks report quarterly results and board changes, such as the election of a new independent director and planned Audit Committee leadership transitions.
Annual reports on Form 10-K and quarterly reports on Form 10-Q (accessible via this page when filed) provide more detailed information on Skyward Specialty’s underwriting divisions, specialty P&C operations, risk factors, and financial statements. These filings also discuss topics such as reinsurance arrangements, reserves, investment portfolios, and non-GAAP financial measures used by management.
Stock Titan enhances these documents with AI-powered summaries that highlight key points from lengthy filings, helping users quickly identify items such as changes in credit arrangements, acquisition terms, or underwriting performance metrics. The filings page is also a resource for tracking any future Forms 3, 4, or 5 related to insider transactions, as well as proxy statements that address board composition and executive-related matters, when such documents are filed with the SEC.
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.
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.