Skyward Specialty Insurance Group, a US-based specialty insurer recognised for its innovative underwriting and workplace culture, has agreed to acquire Apollo Group Holdings Limited, a London-based specialist underwriting platform at Lloyd’s of London, in a deal valued at $555m.
The acquisition is designed to strengthen Skyward Specialty’s presence in the US specialty insurance market and broaden its reach in Lloyd’s, according to InsurTech Insights.
Of the total consideration, $184m will be issued in stock to employees and strategic investors, while $371m will be paid in cash. The deal, subject to regulatory approvals, is expected to close in the first quarter of 2026.
Skyward Specialty is a leading specialty insurance provider in the US, with recognition as one of the “Best Places to Work in Insurance” for three consecutive years.
The company emphasises niche underwriting and has built a reputation for delivering innovative solutions across various specialty lines.
Apollo, founded in 2010, operates through a capital-light, specialty-focused model at Lloyd’s of London.
The firm has maintained a compound annual growth rate of around 20% in gross written premium since inception.
Its Syndicate 1969 underwrites multi-class specialty insurance, while Syndicate 1971, also known as Apollo ibott, delivers liability products tailored to the digital and sharing economy. The company has also been recognised for advancing resilience and sustainability within Lloyd’s.
Skyward Specialty expects the acquisition to be accretive to adjusted operating earnings per share in the first full year and forecasts double-digit growth. It also anticipates adding more than $1.5bn in managed premium, enhancing its competitive edge and underwriting breadth.
Following the deal, Apollo CEO David Ibeson, who has led the company since 2012, and the management team will continue in their roles and join Skyward Specialty.
Apollo CEO David Ibeson said, “We have been building a relationship with Skyward Specialty for nearly two years, and during that time we have had a number of opportunities to collaborate. We very quickly understood that we had a common view of the future of the specialty market and a shared understanding of how to position our respective organisations to win.”
Skyward Specialty chairman and CEO Andrew Robinson said, “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 and fit with our strategy to ‘Rule Our Niche’.”
Robinson added that Apollo’s Syndicate 1969 will broaden access to specialist classes such as political violence, product recall and specialty disruption, while Syndicate 1971 will bring tailored solutions for the new economy to the combined business.
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