Skyward Specialty Acquires Apollo Group for $555M, Expands Lloyd’s Market Presence

Skyward Specialty Insurance Group, a specialist in property and casualty insurance, has agreed to acquire Apollo Group Holdings Limited, a Lloyd's specialist underwriting platform, for $555 million. The acquisition includes $184 million in stock consideration for employees and strategic investors, and $371 million in cash financed through committed debt, with the transaction expected to close in early 2026 upon regulatory approval.

Apollo, which operates through Lloyd's Syndicates 1969 and 1971, has demonstrated strong growth with a compound annual growth rate of approximately 20% since 2010, using a capital-light business model and focusing on specialty lines including Political Violence, Product Recall, and digital economy liabilities.

This transaction will bolster Skyward Specialty's US specialty market presence by adding over $1.5 billion of managed premium and is projected to deliver double-digit adjusted operating EPS accretion in its first full year. The deal also marks Skyward Specialty's entry into the Lloyd's market, establishing a combined group premium exceeding $3 billion.

Key management from Apollo, including CEO David Ibeson, will join Skyward Specialty, ensuring continuity in leadership and strategic alignment. Financial advisory for the transaction involved Barclays, Evercore, and Howden Capital Markets & Advisory, with legal counsel provided by RPC and Willkie Farr & Gallagher LLP.