Skyward Specialty Insurance Group, Inc. (SKWD)

Key figures

The last twelve months reported, with the latest price and balance sheet.

Revenue, last twelve months

$1.7B

Revenue growth

38.3%

Net income, last twelve months

$187.9M

Earnings per share

$4.29

Operating margin

13.9%

Net margin

10.8%

Return on equity

14.8%

Market value

$2.6B

Price to earnings

13.5x

Cash

$219.2M

Debt

$417.6M

Debt to equity

0.33

Shares outstanding

44.4M

Financial statements

Revenue, profit and cash flow by fiscal year, each year linked to its annual report.

By quarter

What the company said with its results

From the second quarter 2026 results, filed 4 August 2026.

• Diluted operating EPS up 46%. Diluted operating EPS was $1.30, against $0.89 a year earlier. Diluted EPS was $1.07, against $0.93. Six-month diluted operating EPS was $2.55, against $1.78.
• Annualized operating ROE 19.0%. Annualized operating ROE was 19.0% for the quarter, against 17.1%. Annualized ROE was 15.7%, against 17.7%. For the six months, operating ROE was 20.4%.
• Net income rose to $49.0 million. Net income was $49.0 million for the quarter, against $38.8 million a year earlier. Six-month net income was $98.8 million, against $80.9 million.
• Managed premiums up 17.5%. Managed premiums were $1,058.7 million, against $900.8 million in the prior-year period. Six-month managed premiums rose 18.5% to $2,026.4 million.
• Gross written premiums up 13.3%. Gross written premiums were $740.6 million, against $653.9 million. Six-month gross written premiums rose 12.8% to $1,408.3 million.
• Fee-generating premiums up 28.8%. Fee-generating gross written premiums were $318.1 million, against $247.0 million. Aligned Syndicates rose 13.4% to $217.2 million, and Partner Syndicates rose 82.0% to $100.9 million.
• Skyward Specialty premiums up 14.2%. Skyward Specialty segment gross written premiums were $667.8 million, against $584.9 million. Six-month segment premiums rose 11.5% to $1,249.6 million.
• Global Agriculture up 95.8%. Global Agriculture premiums were $111.9 million, against $57.2 million. Accident & Health rose 57.8% to $95.5 million, and Specialty Programs rose 29.7% to $111.4 million.
• Captives, energy and property fell. Captives premiums fell 16.6% to $64.3 million, Energy Solutions fell 16.2% to $62.7 million, and Global Property fell 15.3% to $71.1 million.
• Apollo segment premiums up 5.6%. Apollo segment gross written premiums were $72.8 million, against $68.9 million. Syndicate 1969 rose 7.7% to $59.4 million, and Syndicate 1971 fell 2.8% to $13.4 million.
• Combined ratio 89.5% in quarter. Combined ratio was 89.5%, against 89.4% a year earlier. Skyward Specialty was 86.9% and Apollo 97.6%. Ex-cat combined ratio was 87.6%, against 88.0%.
• Expense ratio improved 0.9 points. Expense ratio was 27.2% for the quarter, against 28.1% a year earlier. For the six months it was 27.8%, against 28.1%.
• Skyward Specialty expense ratio fell. The Skyward Specialty expense ratio improved 2.7 points for the quarter and 1.7 points for the six months. Management attributed this to business mix, operating efficiencies, and scale.
• Catastrophe losses 1.9 points. Catastrophe loss and LAE was 1.9 points of net earned premiums for the quarter, against 1.4 points a year earlier. Apollo carried 5.4 points and Skyward Specialty 1.3 points.

Company events

The newest 8-K filings of 36 held.

Every filing

The newest filings with the SEC of 113 held.

Insider trades

Form 4 trades by officers, directors and 10% owners, last 12 months.

Planned insider sales

Form 144 notices, filed when the sell order goes to the broker.

Large holders

Schedule 13D and 13G filings by holders of more than 5% of the voting shares.

Trades by members of the House

From each member's periodic transaction report.

Short interest

Shares sold short and not yet bought back, on each FINRA settlement date.

Funds that hold it

From each fund's latest Form 13F.

276 funds held it at 30 Jun 2026: 127 added and 89 trimmed in the quarter. The largest:

Peers

Companies in the same industry.

• Berkshire Hathaway Inc. (BRK.B): revenue $384.7B, market value $1.17T
• Chubb Ltd. (CB): revenue $61.8B, market value $136.0B
• Progressive Corp. (PGR): revenue $91.1B, market value $131.2B
• Travelers Companies, Inc. (TRV): revenue $48.9B, market value $80.7B
• Allstate Corp. (ALL): revenue $70.1B, market value $63.6B
• American International Group, Inc. (AIG): revenue $26.6B, market value $41.9B
• Arch Capital Group Ltd. (ACGL): revenue $19.2B, market value $35.0B
• Hartford Insurance Group, Inc. (HIG): revenue $29.0B, market value $34.8B
• Everest Group, Ltd. (EG): revenue $16.8B, market value $28.8B
• Cincinnati Financial Corp. (CINF): revenue $13.3B, market value $27.5B

What the company does

Skyward Specialty Insurance Group is an insurance holding company that sells commercial insurance, mostly in the United States, on both a non-admitted (also called E&S) and an admitted basis. It focuses on markets that it describes as underserved or dislocated, or where standard coverage does not meet business needs. The company works through nine underwriting divisions that write lines such as general liability, excess liability, professional liability, commercial auto, group accident and health, property, agriculture, credit, surety and workers' compensation.

How the business is organised

The company reports one segment. Each of its nine underwriting divisions has its own underwriting leadership and technical staff, and teams inside each division specialise further in particular niches. The company calls its approach "Rule Our Niche". For the year ended 31 December 2025, 41% of gross written premiums were written on an admitted basis and 59% on a non-admitted basis.

What it sells

- Accident & Health: medical stop loss for employers that self-insure employee benefits, including group and single-employer captives, written on an admitted basis. - Agriculture and Credit (Re)insurance: treaty reinsurance for agriculture, dairy and livestock revenue protection, mortgage and credit risks. - Captives: group captive programs for companies that want to self-insure, often run with third-party captive managers. - Construction & Energy Solutions: multi-line cover for high-severity exposures, including general liability, excess liability, commercial auto and workers' compensation. - Global Property: property insurance and reinsurance for commercial clients worldwide. - Professional Lines: management liability, professional liability (including cyber) and allied health (including life sciences). - Specialty Programs: business written with program administrators that have scale or proprietary technology in a niche. - Surety: contract, commercial and transactional bonds for small and medium sized businesses, written on an admitted basis. - Transactional E&S: property and general liability for hard-to-place risks without a catastrophe focus, such as start-ups and businesses with limited operating history.

Property insurance represented 34% of gross written premiums. The company also has lines it exited and placed into run-off, which it calls "exited business".

How it reaches customers

The company distributes through retail agents, wholesale brokers, select program administrators and captive managers, choosing the channel that suits each niche. Accident & Health sells mainly through retail and wholesale brokers. Surety sells through retail agents and brokers. Transactional E&S sells only through wholesale brokers.

Where it operates

Four insurance companies carry most of the business. Great Midwest Insurance Company is the largest and writes on an admitted basis in all 50 states and the District of Columbia. Houston Specialty Company writes on a surplus lines basis in 50 states, the District of Columbia and select foreign countries. Imperium Insurance Company writes on an admitted basis in all 50 states and the District of Columbia. Oklahoma Specialty Insurance Company is an approved surplus lines company in 49 states and the District of Columbia.

The company also owns Skyward Re, a captive reinsurer in the Cayman Islands, and three non-insurance companies. These are Skyward Underwriters Agency, Inc., Skyward Service Company and Skyward Specialty No. 1 Limited Company, a UK company that is an authorized Lloyd's corporate member.

The acquisition of Apollo Group Holdings Limited closed on 1 January 2026, and the price was paid in company stock and cash. Apollo is a specialty underwriting platform at Lloyd's of London. Through Syndicate 1969 it underwrites a multi-class specialty portfolio, and through Syndicate 1971 it offers a platform liability product for the digital and sharing economy. It also earns managing agency fees and profit commissions as managing agent to its own and third-party syndicates.

How it manages risk

Claims are mostly handled in-house, with third party administrators used for programs, captives, occupational accident, workers' compensation and run-off claims. For commercial auto, a "quick strike" program sends investigators to the scene of a reported accident, ideally within two hours. Claims handlers are organised by line of business.

The company buys quota share, excess of loss and facultative reinsurance. Its contracts are predominantly one year long and renew mainly in January and June. At 31 December 2025, 98% of its reinsurance recoverables were from reinsurers rated "A-" or better by A.M. Best, or were collateralized.

Its technology rests on SkyBI, an enterprise data repository and business intelligence platform, plus predictive analytics and core policy, billing and claims systems. Its investment portfolio is mainly cash and investment-grade fixed maturity securities, with fixed income at 75.6% of the portfolio.

Who it competes with

The company competes with other specialty and standard insurers and with program administrators. It names Markel Corporation, W.R. Berkley Corporation, American Financial Group, Tokio Marine Holdings, CNA Financial Corporation, Hiscox, RLI Corp., Intact Finance Corporation, Kinsale Capital Group, Arch Capital Group and AXIS Capital Holdings among its notable competitors. It says competition turns on pricing, reputation and perceived financial strength, broker relationships, policy terms, ratings, claims payment speed, and the experience of underwriting and claims teams. The company is regulated by state insurance regulators, and its main insurance companies are domiciled in Texas and Oklahoma.

*From Skyward Specialty's annual report on Form 10-K for the year ended 31 December 2025. [The filing](https://www.sec.gov/Archives/edgar/data/1519449/000151944926000015/skwd-20251231.htm)*

From the company's 10-K.