Captive Review talks to Kevin Poole, general manager of IMAC, about Cayman’s progress over what has been a positive year.
“10,000+ members are participating in group captive programmes in Cayman. That just blew my mind.”
The Cayman Islands captive insurance sector has entered 2025 with a renewed sense of momentum, reflected not only in the volume of new formations but also in strengthening asset bases, rising premiums and increased international visibility.
Speaking with Captive Review, Kevin Poole, general manager of IMAC, laid out a picture of a jurisdiction experiencing both organic and strategic growth, supported by a deepening bench of managers, widening market awareness in the US and a concerted push to elevate Cayman’s presence within global reinsurance circles.
Cayman’s new captive formation numbers indicate a market moving firmly in the right direction. By the end of the third quarter, the jurisdiction had recorded 32 new licensees: 16 Class B(i)s – typically single-parent captives – 15 Class B(iii)s, which tend to be more aligned with reinsurance activity and one Class C, the special purpose vehicle licence.
These figures alone compare favourably with recent years, but the real story lies in the pipeline. “CIMA advised they had 19 applications under review and another five already approved in principle,” Poole explained. Approved-in-principle licences represent structures that are ready to launch as soon as capital is fully paid in. “If all of those came to fruition, we’d be past 50. I’m not necessarily expecting that number, but we should at least pass the 42 from last year,” he adds. In an industry where year-on-year stability is often considered a victory, this trajectory stands out.
The growth is not confined to new formations. Cayman has witnessed significant increases in premiums written and assets under management across the sector. At the close of the third quarter of 2025, premiums rose from $42 billion the previous year to $51 billion, while assets increased from $154 billion to $173 billion.
The distribution of this expansion is particularly revealing. Pure captives added a couple of billion dollars in assets; group captives grew by around $6 billion; reinsurance structures by $8 billion and SPCs by another $6 billion. These parallel streams demonstrate that Cayman’s growth is both broad-based and diversified, rather than reliant on any single licence class.
Group captives: a booming American pipeline
One of the most striking developments has been the expansion of group captive activity, driven largely by mid-market US businesses. When IMAC conducted a review earlier in the year, the results surprised even Poole: “There were at least over 10,000 members participating in group captive programmes in Cayman. That just blew my mind.”
These members come from industries such as transportation, construction, manufacturing and other sectors that have historically gravitated towards group captive solutions. Specialised structures – such as medical stop-loss captives – have also contributed to this increase. Existing participants in trucking or logistics programmes are now joining stop-loss arrangements, providing cross-programme momentum.
There has even been growth from new areas: “Last-mile delivery groups have set up captives – we have the Amazon delivery drivers, for example.” The presence of established group captive providers such as Captive Resources Insurance and their local insurance manager Kensington Insurance Group, Artex, Cottingham & Butler and Holmes Murphy, through Innovative Captive Strategies who work with Global Captive Management locally, ensures Cayman remains a natural home for this market.
US dominance is absolute; nearly all group captive participants are American, with only a handful from Canada. The explanation, Poole says, is not so much driven by hard statistics as by behavioural trends: greater awareness, peer influence and strong producer engagement. “It snowballs. Once one company in a town is in a captive, they talk to their friend and they want to get into it as well. Even though they might compete, they look out for each other from an insurance perspective.”
Smaller brokers have also benefited, particularly those working with group captive providers that allow members to join with their existing intermediaries. This has helped broaden access to captive solutions among clients who might not otherwise have had them presented.
Growth in SPCs and managers
Cayman’s segregated portfolio structures also continue to evolve, with CIMA’s third-quarter statistics now reflecting individual cells. As at September, Cayman had 621 segregated portfolios, alongside 63 PICs (portfolio insurance companies). These numbers have risen even as the total number of SPCs has decreased slightly – from a peak of 154 at the end of 2023 to 139 at the close of Q3 2024 – likely reflecting the winding down of inactive companies.
The management sector has shown similar dynamism. While 2025 has not yet produced a wave of new entrants, several applications are pending and Poole anticipates as many as three new managers by year-end or early 2026. Recent new arrivals include Blue Ocean (reinsurance-focused), Nascent Insurance Management (associated with the Andre Perez group) and Apex Group, which is expanding from fund and asset servicing to captives.
Marketing momentum and international outreach
IMAC has been significantly more active in global outreach, with Poole noting that his travel schedule has been extensive. Cayman has had a presence at numerous key industry events for 2025, including World Captive Forum, CICA, the US Captive Summit, ASHRM, SIIA, ReFocus, the ITC conference in Las Vegas and National Comp. The jurisdiction also returned to RIMS Canada for the first time in years.
While conference ROI is notoriously difficult to quantify, the early signs are positive. At least one reinsurer chose Cayman after discussions at the US Captive Summit, and several new IMAC members and conference attendees trace their engagement back to these events.
Partnerships with Cayman International Reinsurance Companies Association (CIRCA), the jurisdiction’s reinsurance association, have also strengthened, with coordinated appearances at ITC, ReFocus and CIRCA’s flagship ReConnect event in Cayman. IMAC’s partnership with Cayman Finance at joint overseas events also supports a unified Team Cayman approach, maximising the jurisdiction’s visibility.
Cayman’s reinsurance ambitions
Interest in Cayman’s reinsurance sector has grown substantially, with the second ReConnect conference in 2025 seeing marked increases in attendance compared to its inaugural year. In October, CIRCA in partnership with IMAC and Cayman Finance hosted a Reinsurance Roundtable Breakfast in New York featuring Cayman’s Premier André Ebanks, underscoring the government’s commitment to the sector.
A key long-term goal is achieving NAIC “qualified jurisdiction” status. Although no application has yet been submitted, the process is an industry priority. “Everyone is working in the right direction,” Poole says, noting coordinated Cayman representation at NAIC meetings.
Cayman’s Class B(iii) licence continues to serve as an attractive entry point for reinsurers, functioning as an incubator for companies considering a full Class D presence on island. Major managers such as Marsh, Aon, Artex, WTW and more recently, Blue Ocean, are all expanding in this space.
Legislative evolution and regulatory priorities
While Cayman’s insurance law is expected to be updated – including potential new licence classes for reinsurance brokers and MGAs – the timeline is influenced by the jurisdiction’s focus on the FATF’s fifth round of mutual evaluations in December 2027. As a result, enhancements to AML and CFT frameworks remain the near-term priority.
Nonetheless, discussions about refining or adding captive and reinsurance licence categories continue in the background, reflecting the market’s diversification into life and annuity business, affiliated versus unaffiliated structures and other emerging segments.
Beyond regulatory and market developments, Poole highlights IMAC’s continued commitment to education through its scholarship fund, supported largely by the annual Cayman Captive Forum. “This year we awarded around $483,000 in scholarships to 17 students,” he notes. Importantly, the scholarships are open to a wide range of disciplines – not just financial services – which amplifies their impact across the Cayman community.
Across captives, reinsurance, SPCs, management growth and global promotion, Cayman’s industry bodies and government appear more aligned than ever. As Poole puts it, multiple building blocks are now firmly in place, all supporting a single objective: maintaining Cayman’s position as one of the world’s most innovative, adaptive and resilient captive insurance domiciles.
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