The inaugural Cayman NextGen Insurance Forum, hosted by the Insurance Managers Association of Cayman (IMAC) in partnership with the Cayman International Reinsurance Companies Association (CIRCA) and the Cayman Islands Insurance Association (CIIA), took place on May 28, 2026 at the Grand Cayman Marriott Resort. The three organisations united with a shared focus on developing local talent and strengthening awareness of career opportunities across the insurance and reinsurance sector, bringing together more than 130 registered students and early-career Caymanians for a full day focused on future careers in the industry.
Opening remarks from Hon. Michael Myles, MP, Minister for Caymanian Employment & Immigration, set the tone, underscoring the importance of expanding access for Caymanians. Industry leaders Troy Matarazzo (IMAC), Simranjit Singh (CIRCA), and Evelyn Tibbetts-Farrar (CIIA) reinforced a shared commitment to building a stronger talent pipeline through collaboration.
“As the inaugural Forum, the event marks the beginning of deeper, sustained engagement for IMAC with young Caymanians and the future workforce of the insurance sector,” said Troy Matarazzo. “This Forum reflects our commitment to connecting young Caymanians with real opportunities across the sector and highlights the range of pathways available from an early stage.”
A Young Professionals Panel added a practical, career-focused dimension. Moderated by Brittany MacVicar of Cayman Finance, the panel included Lauren Anderton (Cayman Finance), Chad Bodden (Island Heritage), Appolina Winton (Appleby), Sebrina Lewis (CIMA), and Aryana Grant (KPMG). Appolina Winton and Aryana Grant were both previously recognised as CIRCA Rising Stars, reflecting wider efforts to support and highlight emerging talent within Cayman’s financial services industry.
An interactive Q&A session gave students direct access to professionals, covering entry routes, career development, and day-to-day realities across the sector.
The Career Insights Hub extended engagement further, connecting attendees with experts from insurance, banking, investments, compliance, legal, HR, and audit. Participating organisations included the Cayman Actuarial Network (CAN), Cayman Finance, Cayman Islands Monetary Authority (CIMA), Cayman Islands Recruitment Association (CIRA), Workforce Opportunities & Residency Cayman, and Hello2HIRED.