When Vasti O’Connor joined the Cayman Finance Graduate Training Programme in 2025, she had barely heard of reinsurance. A year on, she is a Reinsurance and Finance Intern at Greenlight Re, the firm she was placed with through the programme, working towards her MBA in the evenings and encouraging other young Caymanians to consider a sector she once knew nothing about.
O’Connor was part of the programme’s inaugural cohort of 15 graduates, who began their placements with Cayman Finance member firms in October 2025 following a two-day orientation retreat. She was placed with Greenlight Re, one of the member firms to join the programme. The Graduate Training Programme was launched that year to help small and medium sized financial services firms, which make up around 90% of Cayman Finance’s membership, access and train Caymanian graduate talent. Each participant is placed with a member firm on a one-year contract, paired with an independent industry mentor, and completes a 12-week series of weekly workshops covering both technical industry knowledge and professional skills.
O’Connor’s own route into the industry began with an associate degree at the University College of the Cayman Islands, followed by a Bachelor of Commerce in Accounting at York University. She is now completing an MBA at the International College of the Cayman Islands alongside her role at Greenlight Re, where Greenlight’s flexibility around her evening classes has allowed her to manage both.
Her first real exposure to reinsurance came through an earlier Cayman Finance internship. “Most people talk about auditing or other business roles, but I had never heard of reinsurance,” she said. “I wanted to learn more about it, and when I was placed at Greenlight Re in the reinsurance sector through the graduate training programme, I was glad to get the chance to learn about it properly.”
At Greenlight Re, O’Connor works on cession testing, verifying that the risk premiums and losses recorded match the figures stated in each contract. It was, by her own account, a steep learning curve at first. “With every other internship I had done, I had some idea of what was going on, but here I had no clue at first. All of the terminology and concepts were completely new to me, which was nerve-racking because I felt behind,” she said.
That early uncertainty did not last. O’Connor credits her colleagues’ support, along with study materials and LinkedIn Learning resources provided by the firm, for helping her build a solid foundation. She points to getting the hang of cession testing, and later getting the opportunity to work alongside Greenlight Re’s innovations team, which invests in early-stage insurance start-ups, as the moments she realised she could see a long-term future in the industry.
Beyond the technical grounding, O’Connor says the programme’s professional development workshops have had a very practical payoff. Training on business email etiquette, something she initially assumed she already knew, later helped her catch and correct a mistake, having replied only to one recipient instead of the full group on a message that had been sent to several people. “I could see the connection, and it definitely has helped me throughout the programme,” she said.
The programme has also opened doors that O’Connor says she would not otherwise have found. She has been invited to industry events and introduced to professionals she would not normally have met so early in her career, and describes getting to know her colleagues outside of the office, at Christmas parties and other social events, as one of the most rewarding surprises of working in the industry.
Her advice to any Caymanian student weighing up whether to apply for the Graduate Training Programme is straightforward. “You should apply because the experience that you get, the places that you go to, the people that you meet, you will not get that opportunity outside of this programme. This is a great transition between school and the full-time working world.”
Cayman Finance has opened applications for its 2026 cohort until Sunday, 26 July, expanding the programme from 15 to 22 positions following the success of its first year. The programme remains open to Caymanian graduates who completed university in December 2025 or are due to graduate in 2026, and pairs successful applicants with member firms on one-year contracts, complete with structured training and mentoring.
Danielle Hennings, Director of Finance, Operations and Community Engagement at Cayman Finance, said the programme was designed to give graduates like O’Connor a supported route into the industry. “This is about opening doors for Caymanians and helping them build successful careers in the industry,” she said.
For O’Connor, that door has already led somewhere she did not expect to be a year ago. “I want to be a part of the growth of the reinsurance industry in the Cayman Islands, especially because it is becoming bigger,” she said. “I want to be a part of the growth of it.”
Recent graduates can apply for this year’s programme here: https://caymanfinance.ky/graduate/
