Skyward Specialty Insurance Group, an innovative specialty P&C insurance company, locked down the regulatory and shareholder signoffs it needed for its $555 mn takeover of Apollo Group Holdings, and the company now expects to wrap the deal in the first quarter of 2026.
Minority Apollo shareholders backed the transaction, which doesn’t surprise anyone following the chatter because Skyward has pitched Apollo as a steady-growth, low-volatility play that fits neatly with its specialty strategy.
Apollo runs two Lloyd’s syndicates. Syndicate 1969 writes a multiclass specialty book with a clear lean toward disciplined underwriting, while Syndicate 1971 (Apollo ibott) builds platform liability products for digital and sharing-economy players.
The setup gives Skyward a broader London footprint and a way to scale without taking wild swings, according to Beinsure analysts.
Andrew Robinson, Skyward’s chairman and CEO, said approvals from the UK’s Prudential Regulation Authority and Lloyd’s are now in hand. With that hurdle cleared, the firm shifts to closing mechanics.
The original September announcement put the purchase price at $555 mn, split into $184 mn in stock for employees and strategic backers, plus $371 mn in cash funded with committed debt.
Skyward claims the deal will deliver double-digit adjusted operating EPS accretion in year one and tack more than $1.5 bn in managed premium onto the platform. Maybe ambitious, maybe not, but the company sounds confident.
Skyward also pushed out pro forma guidance for 2026 that bakes in Apollo’s impact. Gross written premiums land between $2.65 bn and $2.8 bn, with net retention around 65%.
The combined ratio sits in the 90.5-91.5 range, including 2-2.5 points of cat losses – a realistic number for this slice of the market.
Net investment income runs $115-120 mn, syndicate management fees $30-35 mn, and commission and fee income $5-8mn.
Net income hits $207-216 mn. It’s a chunky forecast, and honestly, the integration will decide how close they get, but Skyward clearly wants investors thinking bigger heading into 2026.
The Company operates through nine underwriting divisions – Accident & Health, Agriculture and Credit (Re)insurance, Captives, Industry Solutions, Global Property, Professional Lines, Specialty Programs, Surety and Transactional E&S.
Skyward Specialty’s subsidiary insurance companies consist of Great Midwest Insurance Company, Houston Specialty Insurance Company, Imperium Insurance Company, and Oklahoma Specialty Insurance Company.
In November, Skyward announced the promotion of John Burkhart to President, U.S. Property & Casualty, Skyward Specialty Insurance.
This promotion is a key step in aligning talent and operational leadership to support the growth and strategic development of the Company’s U.S.-based business.
In this expanded role, Burkhart will assume oversight of the Company’s Captives & Specialty Programs divisions in addition to his current responsibilities for Professional Lines, Industry Solutions, Surety, Accident & Health, and Transactional E&S. Additionally, Claims, Technology Solution Services (TSS) and Pricing Actuarial will now report to him.
Since joining in 2021, John has been instrumental to Skyward’s growth and a central figure in our success. He has overseen several of our most successful developments and business expansions. His depth of experience, operational prowess, leadership, and the followership he inspires across the organization truly stand out.
” said Andrew Robinson, Skyward Specialty Chairman and CEO
“As we prepare for the next phase of growth, having the right leaders in place is critical to our continued success. I have complete confidence in John’s ability to lead us forward with the same discipline, focus and commitment to our ‘Rule Our Niche’ strategy that has served us so well over the past five years,” said Andrew Robinson.
