Skyward Specialty Insurance Group, Inc.

What they do

Skyward writes commercial insurance products on a non-admitted (E&S) and admitted basis, primarily in the United States, targeting underserved or dislocated markets that need customized underwriting and claims. Its lines include general and excess liability, professional liability (including cyber and media), commercial auto, group accident and health, property, agriculture, credit, surety and workers' compensation, plus some specialty reinsurance in property, agriculture and credit. In January 2026 it acquired Apollo, a Lloyd's of London specialty platform operating Syndicates 1969 and 1971, and both now sit under the Skyward Group holding brand.

Revenue drivers

• Gross written premiums across underwriting divisions — Second quarter 2026 gross written premiums were $740.6 million, up 13.3% year over year. Divisions include Accident Health ($95.5 million in Q2 2026, up 57.8%), Global Agriculture ($111.9 million, up 95.8%), Captives ($64.3 million, down 16.6%), Credit Surety ($63.8 million, up 15.6%), Energy Solutions ($62.7 million, down 16.2%), Global Property ($71.1 million, down 15.3%) and Professional Lines ($35.0 million, down 6.9%).
• Fee generating gross written premiums — Fee generating gross written premiums were $318.1 million in Q2 2026, up 29% year over year, versus $247.0 million in Q2 2025. These are premiums on which the company earns commission and fee income rather than bearing the full underwriting risk.
• Net written premiums — Net written premiums were $485.6 million in Q2 2026, compared with $339.2 million in Q2 2025. Net written premiums are gross written premiums less ceded written premiums, reflecting reinsurance retention decisions.
• Managed premiums — Managed premiums, which include premiums managed through Apollo's Lloyd's syndicates, were $1,058.7 million in Q2 2026, up 17.5% versus 2025 on a pro forma basis. Fee and commission income is earned on this managed and fee-generating premium base.

Recent performance

For the three months ended June 30, 2026, Skyward reported net income of $49.0 million and net operating income of $59.2 million, with basic earnings per share of $1.10 and diluted operating earnings per share of $1.30, up 46% year over year. Gross written premiums rose 13.3% to $740.6 million and managed premiums rose 17.5% to $1,058.7 million. The combined ratio was 89.5%, including 1.9 points of catastrophe losses, and the ex-cat combined ratio was 87.6%. For the six months ended June 30, 2026, net income was $98.8 million and annualized operating return on equity was 20.4%. Reported annual net income has grown from $38.3 million in 2021 to $170.0 million in 2025, with diluted EPS of $4.07 in 2025.

Strategy

Management describes its approach as a "Rule Our Niche" strategy, focused on underserved and dislocated specialty markets where it can build customized products and claims capabilities. The January 1, 2026 Apollo acquisition for $559.1 million ($371.1 million in cash and 3,679,332 shares) added Lloyd's-based specialty underwriting, including a syndicate focused on digital economy, autonomy and platform-based risks, and a capital-light model. Skyward says the U.S. and U.K. businesses continue to operate as distinct market-facing brands under the Skyward Group brand to preserve both franchises while pursuing unified strategy. The company repurchased 223 thousand shares for $9.7 million in the quarter and expanded its share repurchase authorization from $50 million to $100 million. It aims to generate underwriting profitability and book value per share growth across P&C market cycles.

Risks

• Underwriting risk assessment — The company states its financial condition and results could be materially adversely affected if it does not accurately assess its underwriting risk.
• Distribution channel reliance — Its business depends on insurance retail agents and brokers, wholesalers and program administrators, and risks arising from that reliance could adversely affect results.
• Reinsurance availability and recoverability — It may be unable to purchase third-party reinsurance on commercially acceptable terms, and its reinsurers may not reimburse claims on a timely basis or at all.
• Reserve adequacy — Its losses and loss expense reserves may prove inadequate to cover actual losses, which could materially affect financial condition, results and cash flows.

Outlook

Management said it believes the company is "exceptionally well positioned to continue to deliver top quartile results and long-term value for shareholders," citing Q2 2026 diluted operating EPS of $1.30, up 46% year over year, and 20.4% annualized operating ROE for the first half of 2026. CEO Andrew Robinson pointed to gross written premium growth of 13% and fee generating premium growth of 29% to $318 million in the quarter. Book value per share rose to $28.55, up 14.6% from December 31, 2025. The 10-Q notes results for the six months ended June 30, 2026 are not necessarily indicative of the full year.