Cayman Finance is continuing its outreach efforts to insurance risk managers, carriers and advisers across the United States and Canada, showcasing the Cayman Islands’ strengths in captive insurance and reinsurance.
Working alongside the Cayman Islands Government, Cayman Islands Monetary Authority (CIMA), Insurance Managers Association of Cayman (IMAC), the Cayman Islands Reinsurance Companies Association (CIRCA), and industry colleagues, Cayman Finance exhibited at multiple insurance events and participated in key regulatory meetings from August through to October.
At the National Association of Insurance Commissioners (NAIC) Summer National Meeting in August in Minneapolis, the Cayman delegation engaged with US state regulators and industry stakeholders on supervision and policy topics. As part of the week’s engagement, the Cayman delegation held meetings with regulators from 13 states and hosted a happy hour social. Cayman Finance plans to build on this effort significantly at the NAIC Fall Meeting in Hollywood, Florida, which starts on 8 Dec 2025.
Next, Cayman Finance exhibited at the Risk & Insurance Management Society (RIMS) Canada Conference 2025 in Calgary in September, where the Cayman delegation also included representatives from IMAC. The conference engaged corporate risk leaders and brokers on Cayman’s practical regulatory framework and specialist ecosystem. The discussions reinforced the value Cayman brings to Canadian businesses and showcased why Cayman continues to be the jurisdiction of choice for innovative captive insurance and reinsurance solutions.
At the end of September, Cayman Finance joined healthcare risk leaders at the American Society for Healthcare Risk Management (ASHRM) 2025 in Charlotte. “The US healthcare sector represents the largest line of business for captive insurance in the Cayman Islands,” said Cayman Finance Associate Director for Insurance Brittany MacVicar. “ASHRM is therefore a key conference for Cayman Finance to promote the jurisdiction and demonstrate how our captive insurance solutions can meet the evolving risk management needs of healthcare organisations.”
Across the exhibit floor, on a panel covering captive fundamentals, and in targeted meetings with US hospital and health-system stakeholders, MacVicar and Cayman member firms compared notes on emerging risk themes, ranging from workforce safety and claims severity to AI adoption and quality assurance trends.
The Charlotte discussions showed why healthcare remains Cayman’s largest captive line and why collaboration with US providers and brokers continues to deepen. Exhibiting at the conference also allowed Cayman Finance to speak with those unfamiliar with captives about how these structures can be effectively used in their own healthcare companies.
“It gives us the opportunity to reinforce Cayman’s role as the go-to jurisdiction for healthcare captives, demonstrating our industry’s expertise, regulatory soundness, and ability to adapt to the dynamic landscape of healthcare risk management,” MacVicar said.
The outreach continued in New York at The Cayman Islands Reinsurance Roundtable Breakfast in October at the Harvard Club of NYC, organised with CIRCA. This invitation-only forum brought together US and Cayman reinsurance leaders, institutional investors, regulators and advisers for a discussion on capital efficiency, regulatory clarity and growth opportunities. Highlights included a keynote by Cayman’s Premier André Ebanks, a US-Cayman regulatory panel featuring NAIC commissioners, and a session challenging common misconceptions about Cayman’s regime.
“These events are key opportunities for Cayman Finance to showcase the jurisdiction’s proven captive and reinsurance framework and demonstrate how we meet today’s evolving risk challenges,” MacVicar said. “Working alongside IMAC, CIRCA, CIMA, member firms and the Government ensures decision-makers hear a unified Cayman message and understand our industry’s expertise, regulatory soundness and our ability to adapt to the dynamic landscape of risk management.”
The international outreach occurs against the backdrop of Cayman’s expanding international insurance market. In the second quarter of 2025, the Cayman Islands Monetary Authority (CIMA) issued 16 new international insurance licences, bringing the total to 21 for the first six months of the year. The jurisdiction now counts 712 Class B, C, and D insurers, which write approximately US$41 billion in premiums and manage a total of US$152 billion in assets. With nine applications approved in principle and a further 14 under review, 2025 is tracking ahead of 2024’s total of new licences, showing sustained growth in the sector.
Building on this quarter’s activity, MacVicar will continue Cayman Finance’s insurance engagement through to the end of the year, including at the SIIA National Conference in Phoenix from 12 to 14 Oct, ITC Vegas in Las Vegas from 14 to 16 October, the National Workers’ Compensation Conference in Nashville from 11 to 12 Nov, and the NAIC Fall National Meeting in Hollywood, Florida from 8 to 11 Dec.
“Cayman’s status as a top destination for captive insurance companies is often attributed to its responsiveness to market needs and commitment to legislative innovation. Attending the range of conferences this year ensures that we can continue to build this reputation,” MacVicar said.
“By collaborating with Cayman Islands Government, CIMA, IMAC, and CIRCA at these events, we can give prospective clients a complete understanding of Cayman’s comprehensive offering and how we can meet their diverse financial needs,” she added.
Cayman Finance will maintain close collaboration with all key stakeholders including Cayman Islands Government, CIMA, IMAC, and CIRCA and our member firms at these events to present a consistent, client-centred Cayman proposition. The focus remains on regulatory strength, specialist expertise and efficient service as the foundations that continue to support growth in Cayman’s captive and reinsurance sectors.
