Skyward Specialty business insurance

Overview

Skyward Specialty is a specialty insurer based in Houston, Texas, that writes the risks standard carriers decline or price poorly. Its business includes surplus lines general liability and property for wholesale brokers, contract and commercial surety, D&O and E&O, energy and mining risks, programs run by MGAs, captives and medical stop-loss for self-funded employers. Its slogan is "Rule Our Niche."

The NAIC's SKYWARD SPECIALTY INS GRP INC GRP ranked No. 60 among U.S. business insurers by 2025 commercial lines direct premiums written, with $1.41 billion, based on NAIC market share data. That is about 0.29% of the national commercial market. It is not among the 10 largest writers of any single commercial line nationally. The largest lines are:

• other liability, which includes general liability and excess ($511.5 million);
• commercial auto ($315.7 million);
• surety ($168.4 million);
• inland marine ($108.8 million).

The U.S. group has four insurers: Houston Specialty Insurance Company, Imperium Insurance Company, Great Midwest Insurance Company and Oklahoma Specialty Insurance Company. Together they write on both an admitted and a non-admitted (excess and surplus lines) basis. Skyward sells only through agents, brokers and program partners.

The parent, Skyward Specialty Insurance Group, Inc., has traded on Nasdaq (SKWD) since January 2023. On January 1, 2026, it closed its purchase of Apollo, a specialty underwriting platform at Lloyd's of London. Since January 5, 2026, the holding company has used the name Skyward Group. Skyward Specialty and Apollo remain the brands brokers deal with. Andrew Robinson is chairman and CEO.

History

• 2007: Stephen L. Way, founder and former CEO of HCC Insurance Holdings, starts a specialty insurance company in Houston.
• 2010: Way's startup merges with a specialty insurer owned by private equity investors to form Houston International Insurance Group (HIIG).
• 2014: A partnership led by Westaim invests $141.1 million in HIIG. Affiliates of Everest Re and Catlin and Way himself also put in money.
• May 2020: Andrew Robinson, formerly president of specialty insurance at The Hanover and global COO of Crawford & Company, succeeds Way as CEO. HIIG raises $100 million of capital that year.
• November 2020: HIIG renames itself Skyward Specialty Insurance Group.
• January 2021: Skyward buys Aegis Surety from K2 Insurance Services and sells its XPro pest control business to K2. Skyward stays the insurer on XPro, with K2 as MGA.
• January 2023: The IPO prices at $15 a share. Shares are listed on the Nasdaq Global Select Market.
• August 2024: AM Best upgrades the insurers to A (Excellent) from A-.
• June 2025: Skyward buys the assets of Acceleration Aviation Underwriters and launches an aviation unit.
• September 2, 2025: Skyward agrees to buy Apollo Group Holdings for $555 million: $371 million in cash and $184 million in stock. Apollo manages Lloyd's Syndicate 1969, a multi-class specialty book, and Syndicate 1971 (Apollo ibott), which insures digital and sharing-economy platforms. Skyward said the deal would add more than $1.5 billion of managed premium.
• January 1, 2026: The Apollo deal closes on the agreed terms. Apollo's CEO, David Ibeson, continues to run the business.

Business insurance products

Skyward organizes the U.S. business into underwriting divisions. Its second-quarter 2026 gross written premium by division shows the shape of the book:

The E&S unit says it takes companies with loss histories, new ventures and high-hazard operations. A crane and rigging captive and coverage for renewable energy contractors serve parts of the construction market. In September 2026, Skyward hired three people to build out its inland marine unit.

Who it insures

Skyward is not a small business carrier. It does not sell a business owner's policy online. Its customers are mostly mid-sized and harder-to-place companies:

• contractors and energy firms needing bonds or high-hazard liability;
• companies with difficult loss histories that end up in the surplus lines market;
• private and public companies buying D&O;
• healthcare providers and allied health professionals buying malpractice-type coverage;
• employers that self-fund health benefits and need stop-loss.

Cannabis operators can buy D&O and E&O from Skyward, and a cannabis program runs on its paper (see Cannabis business insurance).

Skyward has pulled back where pricing weakened. Second-quarter 2026 premiums fell in global property, captives and energy, and the company blamed competition and lower property rates. Gross written premium still grew 13.3% overall.

How to buy

Your path depends on the product:

1. For E&S liability and property, a retail agent places the account through a wholesale broker with Skyward's E&S underwriters. A licensed surplus lines broker must handle the placement.
2. For surety, admitted lines and professional lines, appointed agents and brokers deal with Skyward's underwriters directly. The surety unit has an e-surety portal for agents.
3. For programs and captives, you buy from the MGA or program administrator that runs the program, with Skyward as the insurer.

There is no online quoting for business owners. See wholesale brokers and surplus lines placement: how hard risks get insured and program business: niche insurance through program administrators for how these channels work.

Claims

Skyward's claims page lists separate routes by line:

• Auto, general liability and professional liability: 888-321-0714. The auto claims line is also the number for accidents with serious injury or death, which Skyward asks you to report immediately.
• All lines by email: [email protected]; fax 888-957-6437.
• Workers' compensation: Gallagher Bassett handles reporting through its PC365 nurse triage line, 833-798-0032.
• Surety: email [email protected].
• Medical stop-loss: use the division's notification and reimbursement forms on the claims page.
• Loss runs: email [email protected]. Unless the request comes through your own agency, put it on company letterhead signed by an owner or officer.

Claims on programs may be handled by the program's administrator; check your policy. Skyward says its adjusters specialize by niche.

Financial strength and ratings

On August 14, 2025, AM Best affirmed the A (Excellent) financial strength rating of all four U.S. insurers, with a stable outlook. In an action reported on September 1, 2026, it affirmed the rating again. It kept A (Excellent) and raised the outlook on the long-term issuer credit ratings ("a") to positive. AM Best cited a sustained run of underwriting profit and consistent investment income. It said the Apollo acquisition raised leverage but kept it within the range expected for the rating. The insurers were rated A- before the August 2024 upgrade. No S&P, Moody's or Fitch ratings appear in Skyward's releases.

Results from the company's August 4, 2026 release:

• Second-quarter gross written premium was $740.6 million, up 13.3% on a pro forma basis.
• The combined ratio was 89.5%.
• Net income was $49.0 million.
• First-half 2026 annualized operating return on equity was 20.4%.
• Book value per share was $28.55 on June 30, 2026, up 14.6% from year-end.

Strengths and weaknesses

For a buyer, Skyward is a specialist market: deep in a few niches and absent from small business products. Its ratings and results have improved steadily since the 2020 turnaround, and the Apollo purchase adds Lloyd's capacity.

• Strengths: It is rated A (Excellent), and AM Best's outlook on the issuer rating turned positive in 2026. Its range is wide in hard-to-place classes, from E&S casualty and surety to energy, mining and aviation. It writes admitted and surplus lines paper in the U.S., and Lloyd's capacity through Apollo since 2026. Claims routes are clear by line, with nurse triage for workers' comp injuries.
• Weaknesses: There is no direct buying or online quoting, so you need an agent or wholesaler. It doesn't write standard small business packages. It has trimmed property, captives and energy as rates softened, so appetite can change from year to year. Integrating Apollo is new, and the acquisition added debt.

How to contact Skyward Specialty