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 is asking shareholders to vote at its virtual 2026 annual meeting on three routine matters: electing two Class I directors, approving executive pay on an advisory basis, and ratifying Ernst & Young LLP as independent auditor for 2026.
The board has nominated incumbent director Gena Ashe and new nominee Peter C. Hearn, both described as independent and experienced insurance and governance leaders, for terms running to the 2029 meeting. The company reports 44,543,065 common shares outstanding as of March 6, 2026, with one vote per share and no cumulative voting.
The proxy outlines a majority-independent nine‑member board with separate audit, compensation, nominating and governance, risk, and investment committees, all largely composed of independent directors. It also describes a say‑on‑pay framework tying executive compensation to performance and notes that Ernst & Young billed $5.24 million in 2025 audit and related fees.
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 director Anthony J. Kuczinski bought additional common stock in open-market transactions. He purchased 2,000 shares at $46.8751 on February 27, 2,000 shares at $48.7911 on March 2, and 1,000 shares at $48.1321 on March 3, 2026, bringing his directly owned stake to 11,903 shares.
Skyward Specialty Insurance Group CFO Taryn Leonie McHarg reported buying a total of 200 shares of common stock of Skyward Specialty Insurance Group, Inc. in open-market transactions. The purchases occurred on February 27, 2026 at prices of $46.71 and $46.49 per share and are held indirectly as shares controlled by the reporting person as custodian. The filing also reports that McHarg directly owned 7,764 shares of common stock following these transactions.
Skyward Specialty Insurance Group director Peirce Christopher Locke bought 3,200 shares of common stock in an open-market purchase. The transaction took place on March 2, 2026 at a price of $47.30 per share. After this trade, he directly owns 3,200 shares.
Skyward Specialty Insurance Group describes itself as a growing U.S.-focused specialty insurer, writing admitted and non-admitted commercial lines across nine underwriting divisions, including accident & health, agriculture and credit (re)insurance, captives, construction and energy, global property, professional lines, specialty programs, surety and transactional E&S. The company emphasizes technical underwriting, advanced analytics and its SkyBI business intelligence platform to target complex, underserved niches and pursue what it calls its “Rule Our Niche” strategy.
The filing highlights the completed acquisition of Apollo Group Holdings Limited, a Lloyd’s-based specialty underwriting platform, on January 1, 2026, paid with a mix of company stock and cash. Apollo adds multi-class specialty business and digital-economy liability products through Lloyd’s syndicates, along with fee and profit-commission income from managing agency services. Skyward describes a diversified property and casualty portfolio, significant use of quota share and catastrophe reinsurance, a maximum property catastrophe program of $36.0 million in excess of $12.0 million, and an “A” (Excellent) financial strength rating from A.M. Best.
The company outlines extensive enterprise risk management, reserving and technology practices, while also listing numerous risk factors. These include potential mispricing of underwriting risk, intense competition, reliance on brokers and program administrators, dependence on third-party reinsurance, reserve uncertainty, economic and inflation pressures, regulatory constraints, cybersecurity threats, and integration risks associated with the Apollo acquisition.
Skyward Specialty Insurance Group Chairman and CEO Andrew S. Robinson reported open-market purchases of a total of 22,100 shares of common stock. The transactions were executed at weighted average prices of $46.57 and $46.94 per share across multiple trades within stated price ranges.
Following these purchases, Robinson directly owns 167,674 shares of Skyward Specialty Insurance Group common stock. Both transactions are classified as open-market purchases and increase his direct ownership stake.
McHarg Taryn Leonie reported acquisition or exercise transactions in this Form 4 filing.
Skyward Specialty Insurance Group, Inc. reported that executive Taryn Leonie McHarg received a grant of 37,854 Restricted Stock Units under the 2026 MIP. Each RSU represents one share of common stock upon settlement. According to the award terms, 50% of the RSUs vest on January 1, 2029 and the remaining 50% vest on January 1, 2030, contingent on continued service. The RSUs were granted at no cash cost per unit. Following this award, McHarg directly holds 7,764 shares of Skyward common stock.
Slaughter James Richard reported acquisition or exercise transactions in this Form 4 filing.
Skyward Specialty Insurance Group, Inc. reported that executive James Richard Slaughter, CUO - Apollo, received a grant of 108,154 Restricted Stock Units (RSUs) on February 25, 2026. Each RSU represents the right to receive one share of common stock upon settlement.
According to the award terms, 50% of these RSUs are scheduled to vest on January 1, 2029 and the remaining 50% on January 1, 2030, contingent on his continuous service. Following this filing, he reports direct ownership of 55,475 shares of common stock and indirect ownership of 12,724 shares through the Hillside Family Trust 2025, where he serves as trustee.
Ibeson David Christopher Ben reported acquisition or exercise transactions in this Form 4 filing.
Skyward Specialty Insurance Group, Inc. reported that Apollo division CEO David Christopher Ben Ibeson received a grant of 21,630 restricted stock units (RSUs) on February 25, 2026 under the 2026 MIP. Each RSU represents the right to receive one share of common stock upon settlement.
Subject to the award’s terms and his continued service, 50% of the RSUs are scheduled to vest on January 1, 2029 and the remaining 50% on January 1, 2030. Following this filing, he holds common stock directly and through The Ibeson Family Trust, where he serves as trustee.