More than 130 students, recent graduates, and early-career Caymanians gathered at the Grand Cayman Marriott Resort on 28 May 2026 for the inaugural Cayman NextGen Insurance Forum, a first-of-its-kind initiative designed to introduce young Caymanians to the diverse career opportunities available within the Cayman Islands’ insurance and reinsurance sectors.

The event was 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). The three organizations united around a common objective: developing local talent and strengthening the future workforce of one of Cayman’s most significant financial services industries.

Opening the forum, Hon. Michael Myles, Minister for Caymanian Employment and Immigration, emphasized the importance of expanding career access for Caymanians and creating pathways into high-value industries. Industry leaders Troy Matarazzo of IMAC, Simranjit Singh of CIRCA, and Evelyn Tibbetts-Farrar of CIIA echoed this message, highlighting the collaborative efforts underway to build a stronger and more sustainable talent pipeline for the sector.

“As the inaugural Forum, the event marks the beginning of deeper, sustained engagement with young Caymanians and the future workforce of the insurance sector,” said Troy Matarazzo, Chair of IMAC’s Talent Development Committee. “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.”

The forum was created to help demystify the insurance and reinsurance industries by showcasing the breadth of career options available beyond traditional perceptions of the sector. Organizers sought to demonstrate that opportunities exist across disciplines including underwriting, actuarial science, compliance, accounting, auditing, legal services, human resources, investments, and risk management.

A key highlight of the programme was a Young Professionals Panel moderated by Brittany MacVicar of Cayman Finance. Panelists included Lauren Anderton of Cayman Finance, Chad Bodden of Island Heritage, Appolina Winton of Appleby, Sebrina Lewis of the Cayman Islands Monetary Authority (CIMA), and Aryana Grant of KPMG. Through candid discussions, panel members shared their personal career journeys, insights into the industry, and practical advice for students and young professionals considering careers in financial services and insurance.

Attendees also participated in an interactive question-and-answer session that provided direct access to industry professionals. Discussions focused on entry routes into the industry, professional development opportunities, educational requirements, and the day-to-day realities of working in insurance and reinsurance.

The event concluded with a Career Insights Hub, where participants engaged in small-group discussions and networking opportunities with professionals from a wide range of sectors. Representatives from organizations including Cayman Finance, CIMA, the Cayman Actuarial Network (CAN), the Cayman Islands Recruitment Association (CIRA), Workforce Opportunities and Residency Cayman (WORC), and Hello2HIRED were on hand to provide guidance on internships, scholarships, career pathways, and employment opportunities.

The strong turnout and enthusiastic participation underscored the growing interest among young Caymanians in the insurance and reinsurance industries. Organizers described the forum as an important first step in a long-term effort to educate, engage, and empower the next generation of professionals while ensuring the continued growth and sustainability of Cayman’s globally recognized insurance market.

As Cayman’s insurance and reinsurance sectors continue to expand and evolve, initiatives such as the Cayman NextGen Insurance Forum are expected to play a critical role in connecting local talent with meaningful career opportunities and strengthening the industry’s future workforce.

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