The Insurance Managers Association of Cayman (IMAC) is once again proud to celebrate four Cayman-based professionals named in the Captive Review Power 50 for 2026. With nearly 2,000 nominations, this prestigious ranking of the 50 most influential individuals in the global captive insurance industry reflect the depth, expertise and leadership within the sector.
Cayman’s 2026 Power 50 Honourees are:
#22 – Paul Macey
President, USA Risk Group (Cayman)
Paul continues to play a central role in shaping USA Risk Group’s growing captive insurance platform, having joined them in 2005. Under his leadership, USA Risk has expanded into one of the largest captive managers in the Cayman Islands, overseeing 65 international insurance companies as of the end of 2025. The firm’s growth has also been reflected in industry recognition, with Paul being named Captive Manager of the Year at the 2025 Captive Review Cayman Awards, and USA Risk being highly commended.
#25 – Kara Ebanks
Head of the Insurance Supervision Division, Cayman Islands Monetary Authority (CIMA)
When it comes to industry regulation, Kara has played a key role in Cayman’s growing reputation as a leading captive insurance domicile. Much of this strength is attributed to the quality of regulation, which she and her team at the CIMA have helped to accomplish. She has spent 19 years at CIMA and has held her current role since 2023. Over that time, she has helped shape a regulatory environment that is widely regarded as accessible and closely aligned with the needs of the captive insurance industry.
#30 – Jenny Pooley
Managing Director and CEO, Strategic Risk Solutions Cayman
Jenny stepped into her leadership role at SRS Cayman in 2023, after joining in 2010, and has helped to establish the firm as the largest captive manager in Cayman by number of international insurance companies managed. SRS Cayman established three more entities in 2025, bringing its total to 121 at the end of that year. Under her leadership, the SRS Cayman team successfully established the first Cayman-domiciled captive for a Japanese Fortune 500 firm in 2026, marking a significant milestone for Cayman’s captive insurance sector.
#33 – Alanna Trundle
President, Global Captive Management
Alanna is a leading figure in Cayman’s captive insurance industry, a strong advocate for raising awareness of the sector, and is instrumental in driving sustained growth at GCM. By the end of 2025, the firm managed 65 international insurance companies, solidifying its position as one of the largest captive managers in Cayman. Under her leadership, GCM was also named Captive Manager Firm of the Year at the recent 2025 Captive Review Cayman Awards, while she received individual industry recognition for her contributions.
These recognitions highlight the exceptional accomplishments of Paul, Kara, Jenny and Alanna, as well as the continued strength and reputation of the Cayman Islands as a leading international domicile for captive insurance. IMAC extends its congratulations to all honourees for their valuable contributions to the industry and wider community.
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