Cayman’s insurance industry continues to be a powerful platform for developing home‑grown talent, offering Caymanian graduates meaningful opportunities to build long‑term careers without leaving the jurisdiction. As part of this commitment to retaining and growing local expertise, GCM Vice President Carmela Sta. Ana recently sat down with Jr. Account Executive Brianna Ebanks to reflect on her journey as the Company’s first Caymanian graduate hire through the Cayman Finance graduate programme, highlighting the value of investing in local professionals and supporting their career progression from the outset.
What attracted you to the captive insurance industry?
When I returned to the Cayman Islands after university, I was open to pursuing different career paths, even if they fell outside of my comfort zone. The Cayman Islands is a financial career hub, and finding out about captive insurance was something of a happy accident. When I applied for my graduate programme, I began to research the companies who were offering positions, and a few were captive insurance managers.
What I found intriguing about captive insurance was the diversity. No two captives are the same. Captive insurance reflected the best aspects of financial services and embodied what I valued in a career: a caring work environment where people value efficiency and quick thinking without making sacrifices to employee wellbeing to achieve their goals.
How does working for a captive insurance manager differ from your expectations?
Captive insurance, or any career within financial services, offers a larger variety of opportunities. In previous experiences in entry-level positions, I would not usually be granted the opportunity to work with many different departments or to engage in tasks outside of my job description. Working with GCM, I have learned to wear many hats, and I continue to learn and take on new responsibilities. I recognize this as an opportunity to challenge myself and gain confidence in my skills to become a well-rounded individual.
The warm welcome I received at GCM has been a very nice surprise. I honestly had no expectations when it came to office culture, as I did not have a lot of experience in that regard. Thankfully, any expectations I had have been thoroughly exceeded working with GCM and captive service providers.
What surprised you the most about the captive insurance industry in Cayman?
I had many pre-conceived notions on what working in a corporate environment would be like. It was somewhat of a culture shock when I began working at GCM—I was welcomed with open arms by a very friendly office that prioritized work-life balance, something that I assumed was simply a fantasy once you entered the workforce. People have been so inviting and helpful while I found my feet in the industry, offering helpful advice and resources to ease my way into the world of captive insurance. At GCM, people want you to succeed and help you to do so.
On the technical side, I had no expectations about what modern accounting looked like. When learning accounting in secondary school, everything was manual and many concepts made my head spin—my only hope was that pursuing it as a career would not be the same experience. I was relieved to find that the process is streamlined and easy to understand, although not without periodic moments of confusion. The GCM team trained me every step of the way, and my colleagues are always ready to answer my questions.
What skills or coursework from your university education have been valuable in Cayman’s captive insurance industry?
I completed my undergraduate studies in Biology, and pivoting to a different career was challenging. However, I believe that completing university, regardless of the course-specific knowledge gained, teaches you the transferable skills necessary to succeed in the working world. For example, I performed a lot of data analysis as part of my coursework, and that has helped me in understanding financial information and reporting that to clients.
Furthermore, communication is a skill that should not be undervalued in the working world. In captive insurance, your relationship with the client is one of the most important things you cultivate. As an insurance manager, we aim to provide clients with a satisfying, seamless experience that requires us to understand their unique needs and adjust our approach to suit them.
As a young woman starting your career, how would you describe your experience in Cayman’s insurance environment?
As a graduate with the Cayman Finance Graduate Programme, I was appointed a mentor at the beginning of my career. It was really refreshing to be able to share my experiences with someone who had been in similar situations and who I could go to with any questions or concerns. It helped me settle into the new role, not only as a new employee but as a young woman entering the insurance industry. My mentor was a woman who I shared many experiences with, thus her insight into my challenges and questions were greatly appreciated.
At GCM, I am privileged to work with and learn from a wide range of female role models and leaders. By looking up to these women in the industry, I am inspired and motivated to pursue my passions, knowing you can balance success in your personal and professional life.
What advice would you give to students who think insurance sounds intimidating or uninteresting?
My main advice would be to remember that insurance has adapted to our current world. The pre-charted career path that many of us picture when thinking of insurance is no longer the only option. There is a place for you here, no matter your background or skillset, if you are dedicated and willing to learn. The industry is much vaster than we realize, and it offers fulfilling work that allows you to broaden your horizons for greater success.
What professional certifications, technical skills, or networking strategies would you recommend to students who want to work in the captive insurance industry?
For captive insurance management, Certified Public Accountant (CPA) and/or the Association of Chartered Certified Accountants (ACCA) qualifications are the standard for any accounting work and would be what I would recommend pursuing first. However, as mentioned before, the captive insurance industry is extremely diverse and there is no “one size fits all” trajectory. Explore what careers are available, consider what you want to pursue, and learn what is necessary for you to achieve that career.
It’s crucial to learn how to work with others, listen attentively to what people need, and deliver solutions with efficiency and care. Captive insurance is client-focused, and working with other service providers dictates the quality of service provided. The basis of this is effective communication between people. Do not be afraid to talk to people—you cannot build relationships with others if you never speak to them!
What would you have done differently in school to better prepare for a career in the captive insurance industry?
I would focus more on taking opportunities that pushed me out of my comfort zone. While an Accounting or Finance degree may be useful, I believe that focusing on the skills needed for roles can often overcome a lack of technical knowledge. I would have pursued more options that taught me how to work as part of team and communicate ideas effectively. This is not to say that no technical knowledge is required. I would still recommend applying for internships or shadowing opportunities in roles that you are interested in.
How did the Cayman Graduate Programme help you decide that captive insurance was the right career path?
The Cayman Finance Graduate Programme provided me with the necessary resources and information to take my first steps into the industry. I would not have gotten this opportunity if not for the programme. Through our training, I learned of the many roles in the finance and captive insurance industries and the career trajectories that were available to me. Additionally, witnessing my colleagues at GCM has been a motivator for me. Seeing their passion for their work and the lives that they lead inspires me to continue down this path.
Own Your Outcomes with a Career in Captive Insurance
As Account Executive Kareem French shared in the recent blog, the resilience offered by captive insurance goes beyond operations. It’s also about the strength and support of your people. At GCM, loving what we do and who we do it with is just as important as delivering trustworthy and innovative outcomes for our clients.
To learn more about our career and mentoring opportunities, reach out to us today!