Brit Group Holdings has appointed James Winn (pictured) as chief underwriting officer and head of office at Brit Re in Bermuda. The subsidiary’s third-party written premiums reached US$150.6 million in the first half of 2026, a 69.8% increase on the prior-year period driven largely by casualty treaty growth, according to the group’s interim results filed in July 2026.
Winn, currently managing director of property treaty at Brit in London, will relocate to Bermuda towards the end of 2026, subject to regulatory approval. He takes over from Jonathan Stephenson in a transition expected to conclude in early 2027.
Stephenson, who joined in September 2024, built the subsidiary’s third-party premium to more than US$250 million since launch, according to Brit, with casualty treaty the primary growth driver. His tenure at Brit Re, which included a seat on the ABIR board of directors, gave the subsidiary a degree of market presence that goes beyond its size.
Winn brings more than 35 years of North American property treaty experience across both Lloyd’s and Bermuda. He began his career in 1990 at CT Bowring Reinsurance as a North American treaty broker, moving into underwriting at Venton Syndicate 376 in 1994. He subsequently spent nearly six years in Bermuda managing the North American property treaty account at Max Re, returning to the Lloyd’s market in July 2011. He joined Brit Global Specialty in February 2015.
That combination of Lloyd’s and Bermuda market experience maps directly to what Brit Re writes. Stephenson noted that the Bermuda operation sees proportional transactions that the London book does not, and Winn’s background across both markets positions him to pursue business that a purely Lloyd’s-based underwriting operation would not typically access.
Alongside Winn, Sam Lewis and Jolie Broomhead, both assistant vice presidents, will relocate from their London teams to support Brit Re’s growth in casualty treaty and D&F respectively. The moves reflect the specific lines the platform is expanding into. Brit Re launched property D&F in January 2026, focusing on complex US-based risks across industrial, manufacturing, and realty sectors. That line requires different origination relationships from treaty reinsurance and one that Broomhead’s move is intended to support on the ground.
Brit Re carries an A (Excellent) financial strength rating from AM Best, affirmed in January 2026 with a stable outlook. AM Best noted at the time, however, that rapid growth in third-party business combined with continued dividend payments to Brit Re’s intermediate parent could put pressure on risk-adjusted capitalization as the platform scales. That tension between growth ambition and capital discipline is one Winn will need to manage alongside expanding the product suite.
Group chief underwriting officer Jon Sullivan said Brit remains committed to building its Bermuda presence and credited Stephenson with creating the foundation for what comes next. Martin Thompson, group CEO, described Brit Re in the group’s 2025 results as giving Brit “access to business and talent outside of London while benefitting from the Brit brand and our deep underwriting expertise.” Winn’s appointment is the next step in that direction.
