Skyward Specialty to Acquire Apollo Group for $555m, Enhancing Footprint in US Specialty Insurance Sector.

Skyward Specialty Insurance Group has agreed to acquire Apollo Group Holdings for $555m, expanding its footprint in the US specialty insurance sector by adding over $1.5bn in managed premiums. The acquisition includes $184m in stock consideration and $371m in cash, backed by secured debt financing. Completion is expected in Q1 2026, contingent upon regulatory consents.

Skyward Specialty Insurance Group has agreed to acquire Apollo Group Holdings for $555 million, expanding its footprint in the U.S. specialty insurance sector by adding over $1.5 billion in managed premiums. The acquisition includes $184 million in stock consideration and $371 million in cash, backed by secured debt financing. Completion is expected in Q1 2026, contingent upon regulatory consents.

The acquisition aligns well with Skyward Specialty’s strategy, bringing new specialty niches and a distinctive new economy offering. Apollo Group Holdings has grown its gross written premium at a compound annual growth rate of approximately 20% since its formation in 2010. Through Syndicate 1969, Apollo underwrites a multi-class specialty insurance portfolio, while Syndicate 1971, known as Apollo ibott, delivers a unique platform liability product for the digital and sharing economy. The transaction is expected to deliver double-digit adjusted operating EPS accretion in the first full year post-acquisition.

Skyward Specialty Chairman and CEO Andrew Robinson commented, “We are delighted to reach an agreement to acquire Apollo. Their underwriting leadership and unique market positioning are exceptionally well-matched to Skyward Specialty’s strengths and vision. Apollo’s Syndicate 1969 will provide access to attractive and hard-to-reach specialty classes, while Syndicate 1971 will further enhance our portfolio with unique and innovative solutions designed for new economy industries.”

The acquisition is expected to add more than $1.5 billion of managed premium to Skyward Specialty, reinforcing its position as a leader in U.S. specialty markets. The transaction will also bring Apollo’s advanced technology capabilities to Skyward Specialty, accelerating innovation and growth.

Barclays acted as financial advisor to Skyward Specialty and provided committed financing for the transaction, while Evercore acted as lead financial advisor to Apollo. Willkie Farr & Gallagher LLP acted as legal counsel to Apollo.

References:
[1] https://www.ainvest.com/news/skyward-specialty-insurance-acquire-apollo-group-holdings-555-million-2509/
[2] https://investors.skywardinsurance.com/news-releases/news-release-details/skyward-specialty-insurance-group-acquire-apollo-group-holdings