Cayman reinsurance: if you build it, they will come

The Cayman reinsurance industry is growing fast – and there’s more to come, according to a panel discussion on the first day of the Cayman Captive Forum 2025.

Moderated by Brittany MacVicar, associate director, Cayman Finance, the panel featured Isaac Espinoza, chief executive of Kettle; Ghislain Ghyoot, director at Aon Insurance Managers; and Joy Domingo, director, WTW. Together, they provided a candid and detailed account of where the market has come from, why Cayman has become a preferred domicile, and what lies ahead.

MacVicar opened by situating reinsurance within Cayman’s broader financial ecosystem. She emphasised that the jurisdiction’s rise as a reinsurance hub follows the same formula that propelled its global leadership in hedge funds: political stability, high-quality regulation, access to deep financial expertise and responsiveness to global market needs.

As of Q3 2025, Cayman’s international insurance sector comprises 719 licensees, $51 billion in premiums and $174 billion in assets. While reinsurers represent only 16% of licence holders, they now account for more than 70% of total premium written, an indicator of the sector’s outsized influence and its rapid transformation from niche to global relevance.

Ghyoot traced the origins of this growth back nearly a decade. Cayman’s regulatory regime, particularly the proportional, flexible Class B(iii) model, which has proved especially attractive to start-ups, MGAs, collateralised reinsurers and Insurtechs seeking an efficient, cost-effective domicile without the heavy infrastructure requirements of larger jurisdictions. Momentum grew in the late 2010s as peers exchanged success stories, creating a network effect that drew new entrants into the market.

The hardening US property market, driven by catastrophic losses and shifting climate patterns, accelerated this trend. Regional carriers and MGAs sought alternative capacity, and Cayman structures provided a ready solution. Life and annuity players followed, leveraging Cayman’s proximity to fund managers and private capital.

Domingo added that Cayman’s reinsurance managers, each themselves licensed and regulated by CIMA, play a pivotal role in this process. From pre-formation planning to licencing, operations and strategic transactions, they guide clients through regulatory expectations, help select appropriate service providers, and ensure the evolving regulatory landscape is clearly navigated. The depth of Cayman’s professional services—actuaries, auditors, lawyers and administrators—has become a competitive advantage in itself.

Espinoza drew on his experience with both Root Insurance and Kettle to highlight why InsurTech companies, in particular, have gravitated to Cayman. Many lack legacy carrier infrastructure yet are well capitalised by venture capital or private equity. Cayman’s ability to licence entities quickly, work seamlessly with remote management teams and accommodate innovative underwriting models made it an obvious solution.

He likened the trend to the “Field of Dreams” effect, named after the film of that name: once early adopters like Root and Lemonade demonstrated the model worked, others followed rapidly. The result is a maturing ecosystem where MGAs and Insurtechs increasingly use Cayman reinsurers to demonstrate alignment, take risk on their own programmes and scale more efficiently than through a full carrier structure.

The panel also emphasised the importance of the Cayman International Reinsurance Companies Association (CIRCA). Formed as the industry expanded, CIRCA works closely with CIMA, the Ministry of Financial Services and associations like Cayman Finance and IMAC to promote the jurisdiction, advocate for regulatory consistency and tackle misconceptions.

MacVicar noted that part of the advocacy effort involves “myth-debunking”—countering outdated or misinformed perceptions often recycled in international media. Ghyoot underscored that Cayman maintains stringent standards on AML, KYC and governance, sometimes more rigorous than expectations faced onshore. As he put it, large corporations are often surprised to discover just how thorough Cayman’s due diligence requirements are.

Asked what lies ahead, Espinoza highlighted one development with potentially transformative impact: Cayman’s pursuit of Qualified Jurisdiction status under the US NAIC framework. Without it, reinsurers must often post substantial collateral, sometimes at levels well beyond the risk-based amount. Achieving this designation would significantly reduce redundant collateral, free up capital and accelerate new formations.

The panel also pointed to continued growth in MGA-backed reinsurers, life and annuity structures, crypto-enabled capital entering the risk market, and an expanding pool of local talent. Events such as ReConnect and Cayman Reinsurance New York have helped further establish Cayman on the global stage.

Espinoza closed by noting that the reinsurance boom has direct benefits for the captive industry. As more reinsurers establish themselves locally across an increasingly diverse set of lines—life, property, healthcare, workers’ compensation, general liability, motor, and more—captives gain faster access to capacity, surplus relief solutions and counterparties within the same jurisdiction. This creates a more efficient marketplace and strengthens Cayman’s reputation as a centre for sophisticated risk management.

The panel made clear that Cayman’s reinsurance sector is not an overnight success but the culmination of deliberate regulatory design, strong professional infrastructure and a reputation for responsiveness. With continued innovation, deepening collaboration among stakeholders and the prospect of achieving Qualified Jurisdiction status, Cayman appears well positioned to redefine the road ahead—not just for reinsurance, but for global risk finance more broadly.

Did you get value from this story?  Sign up to our free daily newsletters and get stories like this sent straight to your inbox.