After completing the Office Administration and Human Resources programmes through Inspire Training Cayman, Leslie Range, Executive Account Assistant, joined Global Captive Management Ltd. (GCM) for a captive insurance internship. In this Q&A, Leslie sat down with Jessica Dontas, Vice President, to reflect on how she was introduced to captive insurance, how she built practical skills, and her transition into a full-time role with the team.
How did you discover GCM, and what attracted you to joining our team?
I first came across the opportunity through Inspire Training Cayman. They were looking for internship placements that matched the interests and skills of graduates, and GCM was one of the opportunities available.
At the time, I did not know much about captive insurance or how the industry worked. When the programme coordinator asked if I would be interested in interviewing with GCM, I started researching captive insurance and became genuinely interested in learning more about it. That motivated me to pursue the opportunity.
I remember being nervous during my interview because I had limited knowledge of the industry at that point. However, when I was offered the internship, I was excited for the opportunity. I made it my goal to learn as much as possible about captive insurance and how it works during my time as an intern.
What attracted me most to joining the team was the positive work environment, the collaborative culture, and the workflow. Those aspects made me feel that this was a place where I could grow professionally and continue building my career in the industry.
Captive insurance can be a very specialized industry. What was the biggest thing you learned about the industry and how our team works during your internship?
One of the biggest things I learned during my internship was how much attention to detail, organization, and teamwork are required in the captive insurance industry. I gained a better understanding of the importance of compliance, financial reporting, and maintaining strong relationships with clients to ensure everything runs smoothly.
I also learned how valuable collaboration is within the team. Everyone was approachable, supportive, and willing to share their knowledge, which created a great learning environment. Seeing how different departments work together to meet deadlines and support clients helped me develop both my technical skills and my confidence in a professional setting.
Can you walk us through some of the projects or responsibilities you took on as an intern and how your role evolved over time?
During my internship, I started by supporting the team with administrative work, including maintaining key documents and trackers, preparing tax forms and organizing materials for signature. These responsibilities helped me learn GCM’s processes and understand how careful, accurate work supports the broader team and our clients.
As I became more familiar with the company’s processes, I took on more responsibility, including processing payments, performing callback verifications, maintaining cash books, assembling board materials and drafting meeting minutes. Over time, I was trusted to handle more complex financial and corporate administration work independently. That experience strengthened my technical and organizational skills and gave me a deeper understanding of GCM’s operations and the captive insurance industry.
What skills did you develop during your internship that helped prepare you for the transition into a full-time role?
One of the most valuable skills I developed during my internship was adaptability. As I took on more responsibilities, I learned to manage multiple tasks and maintain accuracy in my work. I also strengthened my communication and teamwork skills by collaborating with colleagues and supporting daily operations. These experiences helped me become more confident, detail-oriented, and prepared to transition into a full-time role.
Working in a Cayman-based business that supports clients across different locations, what have you learned about working as part of a broader team?
Working in a Cayman-based business with clients and colleagues across different locations has helped me understand the value of clear communication, reliability, and a proactive approach as being essential to keeping processes running smoothly and delivering consistent service.
Being part of a broader team has also given me a greater appreciation for how different departments and individuals contribute to the overall success of the business. It has helped me better understand how my work impacts others and the importance of staying accountable to achieve common goals.
What surprised you most about working in and around the captive insurance industry?
What surprised me most about working in the captive insurance industry was how much teamwork and coordination happens behind the scenes.
When I first started, I thought my role would be focused on completing individual tasks, but I quickly realized how connected everyone’s work is. Each task played a part in helping the team deliver quality service to clients. Seeing how different departments collaborate every day showed me how important communication and attention to detail are, and it made me feel like I was contributing to something much bigger than my own responsibilities.
Who had the biggest impact on helping you learn and grow during your internship, and what did you learn from them?
The people who had the biggest impact on my growth during my internship were Tamara Mayers and Kareem French. They guided me throughout my journey, were always willing to answer my questions, and took the time to explain processes and share their knowledge. Their support helped me build confidence, take on new responsibilities, and continue learning.
The entire team also played an important role in my development. Everyone was always willing to help, offer guidance, and share their experience whenever I needed support. Their mentorship and encouragement helped me grow both professionally and personally throughout my internship.
What was the transition from intern to full-time employee like, and how has your role changed since joining the team?
The transition from intern to full-time employee felt very natural because my internship gave me a strong foundation and helped me become familiar with the team’s processes and day-to-day responsibilities.
Since joining the team in a full-time capacity, my role has continued to evolve. I now handle more complex tasks and have taken on greater responsibility within the team. These opportunities have helped me contribute to the team’s success, and the transition has allowed me to keep learning, grow professionally, and play a more active role in supporting both the team and our clients.
What would you say to other Caymanians about the opportunities that programs like Inspire Training Cayman can create?
I would encourage other Caymanians to keep an open mind about Cayman Islands financial services careers because programmes like Inspire Training Cayman can open doors you may not have considered before. Through my experience, I gained valuable skills, hands-on experience and the opportunity to learn from professionals who were willing to support my growth. What started as an internship became a full-time career, and it showed me that with the right attitude and willingness to learn, there are many opportunities to develop both personally and professionally within the industry.
If you are exploring captive insurance careers in the Cayman Islands and want to learn more about potential GCM careers, reach out to our team to connect today!