OAK Global is launching a new strategic business unit, OAK Enterprise, which will be focused on underwriting retrocession business with an appetite for property and specialty classes.
The newly formed Lloyd’s Syndicate 1440 has received in-principle approval to assume business incepting Jan. 1, 2026, targeting approximately $75 million GWP in its first year.
Roland Morse will head the strategic business unit and assume the role of chief underwriting officer, OAK Enterprise.
OAK Reinsurance, the flagship strategic business unit in the OAK Global group, will continue to focus on underwriting primary reinsurance through Lloyd’s Syndicate 2843, headed by James Irvine as chief underwriting officer, OAK Reinsurance.

Morse and Irvine report to Cathal Carr, OAK Global’s founder, chief executive officer and active underwriter for both syndicates.
Syndicate 1440 will be managed under a turnkey arrangement with Polo Managing Agency and will benefit from Bain Capital’s underwriting capital support.
“The reinsurance marketplace is evolving – secular trends driven by continued technology advancements and cyclical dynamics such as M&A are driving new opportunities for our business as clients and distribution partners move toward centralized coordination of risk management,” according to Carr in a statement.
“OAK Reinsurance was established to provide clients with holistic primary reinsurance solutions across property, specialty and credit horizontal risks,” Carr added.
“The creation of OAK Enterprise aims to address increasing demand and opportunity across the vertical risk spectrum, enabling us to provide partnership solutions to our clients with retrocession and enterprise risk management needs, supported by our market leading underwriting expertise,” he said.
“We are proud to receive in-principle approval to launch our second full syndicate at Lloyd’s, introduce OAK Enterprise as a strategic business unit and elevate our group identity to OAK Global. We are very grateful for our partnerships with clients, brokers, capital providers and Lloyd’s in 2025 and we look forward to continuing to create value for our stakeholders going forward,” Carr said.
Elena Lieskovska, a partner at Bain Capital, commented: “We are proud of our partnership with the OAK Global team, and we are pleased to support Syndicate 1440 as a key capital partner.”
“The creation of a retro-focused syndicate at Lloyd’s further evidences our capability to align evolving risk demand with technical underwriting expertise and innovative capital structuring,” said Deepon Sen Gupta, OAK Global’s head of Capital Partnerships. “Syndicate 1440 will offer clients highly rated capacity while providing investors the opportunity to access strong expected returns in an attractive retro market environment.”
Source: OAK Global
Topics Excess Surplus New Markets Lloyd's
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