Every 8-K that Skyward Specialty Insurance Group, Inc. (SKWD) has filed with the SEC in the last 24 months is listed below, newest first, and each one links through to the document itself with the summary and the scores our analysis gives it.
A 8-K covers material events a company has to report between its quarterly reports, so if you follow SKWD and want that one kind of document rather than the whole filing history, this is the page to keep. The company's other filings, of every form, are on the full SKWD filings page.
Skyward Specialty Insurance Group, Inc. (SKWD) reported a planned CFO transition. Chief Financial Officer Mark Haushill has notified the company of his intention to retire effective March 31, 2027. From March 31, 2027 through December 31, 2027, he will serve as Senior Advisor under a Senior Advisor Letter Agreement, receiving an annualized base salary of $250,000 without eligibility for bonuses or new equity awards, while existing equity awards continue to vest under their ordinary terms. The company states his retirement decision did not result from any disagreement regarding operations, policies, or practices.
Taryn McHarg, currently Deputy Chief Financial Officer of the company and Chief Financial Officer of Apollo, will become CFO effective upon Haushill’s retirement and will also serve as Principal Financial Officer and Principal Accounting Officer. Under her existing employment terms, she receives an annual base salary of approximately $540,000 (£400,000), with a target bonus opportunity of 20% to 60% of base salary, and holds a $1,750,000 restricted stock unit award granted in connection with the Apollo acquisition, vesting in two tranches on the third and fourth anniversaries of closing. Her compensation as CFO is expected to be reviewed in the first quarter of 2027.
Skyward Specialty Insurance Group, Inc. reported strong second quarter 2026 results, with managed premiums of $1,058,675 (in thousands), up 17.5% from 2025, and gross written premiums of $740,554 (in thousands), up 13.3%. Net written premiums were $485,616 (in thousands). Net income was $49,038 (in thousands), and net operating income was $59,198 (in thousands). Diluted operating earnings per share were $1.30, which the company states increased 46% year over year.
The combined ratio was 89.5% and the ex‑catastrophe combined ratio was 87.6%, reflecting solid underwriting performance. For the six months ended June 30, 2026, annualized return on equity was 17.3% and annualized operating ROE was 20.4%. The company repurchased 223 thousand shares of common stock for $9.7 million and expanded its share repurchase authorization from $50 million to $100 million. Book value per share reached $28.55, a 14.6% increase compared to December 31, 2025, and stockholders’ equity was $1,267,537 (in thousands) at June 30, 2026.
Skyward Specialty Insurance Group, Inc. expanded its share repurchase authorization on July 15, 2026. The Board approved increasing the aggregate limit from US$50 million to up to US$100 million of outstanding common shares.
The company may buy back stock over time through open-market purchases, privately negotiated transactions, block trades or accelerated share repurchase agreements, including transactions conducted under Rule 10b-18 and Rule 10b5‑1. The program is discretionary, does not require any minimum repurchases, and may be modified, suspended or terminated at any time.
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 reported strong first quarter 2026 growth following its Apollo acquisition. Net income rose to $49.7 million, or $1.09 per diluted share, compared with $42.1 million, or $1.01, a year earlier. Operating income reached $56.8 million, or $1.25 per diluted share, up from $0.90.
Gross written premiums were $667.7 million, up 9.9%, while managed premiums grew 19.6% to $967.7 million. The consolidated combined ratio improved to 89.5%, with an ex‑cat combined ratio of 87.7%. Annualized return on equity was 17.8% and operating ROE 20.3% for the quarter.
Book value per share increased to $27.50, a 10% rise from December 31, 2025, while stockholders’ equity climbed to $1.22 billion, driven largely by stock issued for the Apollo acquisition. Net investment income grew to $27.1 million, supported by a larger, higher‑yielding portfolio.
Skyward Specialty Insurance Group, Inc. completed its acquisition of Apollo Group Holdings Limited on January 1, 2026 and is now filing an amended report to add detailed financial information for Apollo and the combined business.
The amendment includes audited Apollo consolidated financial statements for 2025 and 2024, prepared under United Kingdom GAAP with a qualitative reconciliation to U.S. GAAP. In 2025 Apollo reported gross written premium of $405,862 thousand, profit for the financial year of $49,709 thousand and total comprehensive income of $51,267 thousand. As of December 31, 2025 Apollo’s total assets were $1,156,880 thousand and net assets were $216,573 thousand.
The filing also provides unaudited pro forma combined financial information for Skyward Specialty and Apollo, including a pro forma combined balance sheet as of December 31, 2025 and pro forma combined statement of operations for the year then ended, giving investors a view of how the merged group would have looked on a full-year basis.
Skyward Specialty Insurance Group, Inc. approved a new form of executive employment agreement to be used with its executive officers. The agreement sets each executive’s annual base salary and target bonus, which the board or its committees will review and may adjust at least once a year.
The company entered into this agreement with Chairman and CEO Andrew Robinson and President, U.S. Property and Casualty, John Burkhart. Mr. Robinson’s agreement, effective April 1, 2026, provides for a base salary of at least $1,100,000, a target bonus of 150% of base salary, and an annual long-term equity award with a grant date fair value of at least $4,000,000, subject to board discretion.
Mr. Burkhart’s agreement, effective January 1, 2026, provides for a base salary of at least $600,000, a target bonus equal to 100% of base salary, and an annual long-term equity award with a grant date fair value of at least $1,000,000, also subject to board discretion. The agreements include severance benefits if employment ends without cause or for good reason, potential bonus and equity vesting, COBRA premium reimbursement for up to 12 months, and non‑competition and non‑solicitation restrictions after employment ends.
Skyward Specialty Insurance Group reported a very strong fourth quarter and full-year 2025. Q4 2025 net income rose to $43.2 million, or $1.03 per diluted share, from $14.4 million, or $0.35, in Q4 2024. Full-year 2025 net income reached $170.0 million, or $4.07 per diluted share, up from $118.8 million, or $2.87, in 2024.
Gross written premiums were $439.5 million in Q4 2025, a 13.2% increase, and $2.17 billion for 2025, up 24.3%, driven by accident & health, specialty programs, surety, and agriculture and credit (re)insurance. The Q4 combined ratio improved to 88.5%, with an ex-cat combined ratio of 87.7%, and the full-year combined ratio improved to 89.3%.
Adjusted operating income was $48.9 million in Q4 2025, or $1.17 per diluted share, versus $33.2 million, or $0.80, a year earlier. For 2025, adjusted operating income was $167.4 million, or $4.00 per diluted share. Return on equity for the year was 18.9%, and book value per share increased to $24.92 at December 31, 2025, up 26% from December 31, 2024.
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. 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, 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.
Skyward Specialty Insurance Group, Inc. agreed to acquire Apollo Group Holdings Limited for $556,000,000, buying approximately 87% of Apollo now and aiming to acquire 100% at closing. About 33% of the purchase price will be paid with common stock: the Company will issue 3,679,332 shares as consideration to certain sellers and pay the remainder in cash.
The cash portion is expected to be funded in part by a new $300 million term loan underwritten by Barclays. Completion is expected in the first quarter of 2026 but is subject to signing additional short-form agreements with minority sellers and receipt of regulatory approvals, including from the UK Prudential Regulation Authority, Lloyd's and the Bermuda Monetary Authority. If closing conditions are unmet by June 2, 2026, the majority SPAs terminate automatically.