Skyward Insurance (SKWD) Chief Executive Andrew Robinson told attendees at the KBW Insurance Conference on September 10 that certain areas of the insurance market are softening faster than anything he has witnessed in his 35-year career, even as the company pointed to strong financial metrics and a transformative acquisition completed earlier in 2026.
Shares of Skyward traded around $56 in morning action on Thursday, down 0.39% from the prior close, within a 52-week range of $40.60 to $65.69. Robinson cited a regression analysis suggesting the stock could reach $80 within 12 months, noting the company's P/E ratio of 13.5 and PEG ratio of 0.37, along with 14 consecutive quarterly earnings beats since its January 2023 IPO at $15 per share — the first company to go public globally after the SPAC desert.
The firm completed its acquisition of Apollo at the start of 2026, adding a Lloyd's platform, the ibott digital-economy platform, and two specialty syndicates (1969 and 1971). Apollo also brought Uber as its sole autonomous-vehicle insurance partner and a partnership with DoorDash that generates terabytes of proprietary usage-based data. Robinson said the data moat created by such partnerships is "virtually unassailable" because insurers have no incentive to share proprietary information broadly.
On the Middle East front, Apollo reduced its total insured value exposure to approximately $500 million or less. Last quarter's losses in the region were limited to $2.5 million to $3 million, primarily from a single vertical loss, according to Tarrant.
Revenue growth over the last twelve months was reported at 38%, with a return on equity of 17%. Compound annual growth since the IPO has been in the high-teens, and returns on capital have consistently ranged from the high-teens to the low-20s. Controlled premium stands at roughly $4.5 billion, of which about $3 billion is reported gross written premium; approximately half of that portfolio sits in non-cyclical or less cycle-exposed lines. Catastrophe loss contribution is guided at a combined ratio impact of 2.5%.
The accident and health segment is growing more than 25% annually with high-20s returns on capital, concentrating on medical stop-loss products for employers with 500 or fewer employees. Medical cost inflation is running in the high-teens. Skyward ranks fourth among the top 50 insurers by loss ratio, according to National Association of Insurance Commissioners data.
The surety business has expanded from $3 million when Robinson joined six years ago to approximately $200 million, making it the 14th-largest surety writer in the United States. The agriculture unit includes global government-subsidized crop insurance and a U.S. dairy and livestock program launched in 2019.
Voluntary employee attrition is 4%, well below the industry average of about 10%. The company has been named a Business Journal best place to work for four consecutive years and listed by Newsweek as one of America's top companies.
