Cayman’s insurance and reinsurance sector is putting more focus on local talent, with more than 130 students and early-career Caymanians attending a new forum to introduce them to possible career paths in the industry.
The inaugural Cayman NextGen Insurance Forum was held on May 28, 2026 at the Grand Cayman Marriott Resort. It 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 event brought together students, young professionals, industry representatives, and public officials for a full-day programme centred on employment access, career development, and the range of roles available across insurance, reinsurance, and related financial services.
Representatives from the three organising bodies addressed attendees, with Troy Matarazzo of IMAC, Simranjit Singh of CIRCA, and Evelyn Tibbetts-Farrar of CIIA discussing the need for closer industry collaboration in developing future talent.
“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. 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,” Matarazzo said.
A key part of the programme was a young professionals panel moderated by Brittany MacVicar of Cayman Finance. The discussion featured Lauren Anderton of Cayman Finance, Chad Bodden of Island Heritage, Appolina Winton of Appleby, Sebrina Lewis of CIMA, and Aryana Grant of KPMG.
The panel focused on practical questions about entering the sector, building a career, and understanding the day-to-day demands of different roles. Appolina Winton and Aryana Grant had both previously been recognised as CIRCA Rising Stars, an initiative tied to emerging talent in Cayman’s financial services industry.
Students were also able to ask questions directly during an interactive session with professionals from across the sector. Topics included entry routes, career progression, and what young Caymanians can expect from work in insurance, reinsurance, compliance, legal, audit, HR, banking, and investments.
The forum also featured a Career Insights Hub, which connected attendees with representatives from the Cayman Actuarial Network, Cayman Finance, the Cayman Islands Monetary Authority, the Cayman Islands Recruitment Association, Workforce Opportunities & Residency Cayman, and Hello2HIRED.
The event marked the first joint forum of its kind by IMAC, CIRCA, and CIIA, with the three organisations positioning the programme as part of a broader effort to increase awareness of industry opportunities among early-career professionals.
