Topsail Re has hired a new chief information officer and announced two internal promotions, the latest in a run of personnel moves by the Cayman Islands-domiciled reinsurance firm as it invests in both technology leadership and homegrown talent.
Jason Callaway (pictured above) joins as CIO and executive vice president, taking a seat on the executive team. He brings more than 20 years of experience in global reinsurance and P&C, with previous roles at Swiss Re, XL Group (later AXA XL), and Vantage Risk, where he led technology strategy, cloud and data initiatives, and digital product teams.
The hire comes at a time of heightened demand for technology leadership across the re/insurance sector. CIO.com reported in February that executive recruiters were optimistic about CIO hiring prospects heading into 2026, with regulated industries including financial services seeing particular demand.
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Within the sector, Brown & Brown and USAA have both named new CIOs in recent months, while Reinsurance Group of America's CIO resigned in March.
Sollers Consulting's Marcin Jaremko has noted that the reinsurance sector has historically lagged behind primary insurance in technology adoption, in part because submissions are fewer but more complex.
NTT Data's InsurTech Global Outlook found in 2025 that 74% of insurers ranked digital transformation and technology adoption as their top priority.
Separately, Mike Swartz has been promoted to senior vice president of underwriting after more than two and a half years with the company. Kimberly Ellick has been promoted to senior underwriting assistant after two years in which she contributed to several internal initiatives, including the ImageRight implementation, SICS reconciliation, and training support for new team members.
The promotions follow a broader pattern of internal investment at Topsail Re, which has made several senior external hires in recent months.
Founded in late 2018 by former JLT Re and Axiom Re executive David Johnson, Topsail Re is a closely held total return reinsurance firm with affiliated offices in Greensboro, North Carolina. The Insurer put its total assets at more than $825 million as of 2023.
The company was added to Mutual Re's ownership group effective January 1, 2026, joining Farm Bureau Mutual Insurance Company of Michigan, Motorists Mutual Insurance Company, and others in a combined group with more than $5 billion of policyholder surplus.
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