FORTY Under 40: Jessica Dontas

Jessica Dontas, vice president, Global Captive Management.

Dontas is responsible for overseeing the management of a broad portfolio of captive insurance and reinsurance companies. She also plays an active role in new business development and the formation of emerging entities, working closely with clients to establish and scale solutions tailored to their needs.

Dontas began her career in the United Kingdom, earning a degree in business, accounting and finance from the University of Newcastle, a programme delivered in partnership with PwC and the ICAEW. Since relocating to Cayman in 2013, she has spent more than a decade building deep expertise across the financial services industry.

As a mother of a young family, Dontas is passionate about supporting and mentoring women in the financial services community, championing pathways for growth and balance at every stage of a career.

Looking back at your journey over the past year, what accomplishment are you most proud of, and how has becoming a FORTY Under 40 finalist influenced your perspective on that achievement?

Over the past year, the accomplishment I’m most proud of is stepping outside my comfort zone and seeking out more public speaking opportunities, something I’ve long wanted to do but often held back from. The highlight was participating in a panel at the 2025 Cayman Captive Forum, where I collaborated with respected industry peers to create the panel submission and ultimately speaking during a morning session.

Becoming a FORTY Under 40 finalist hasn’t changed how I view this achievement, but it is a nice confidence boost and a platform to talk about my own experiences. I hope by talking more about my own insecurities and experiences encourages others who feel unsure or not quite “ready” to pursue something new: set a goal, take the first step, and give yourself a chance.

What key challenge did you face in your work this year? How did you overcome it and what did it teach you about leadership at this stage of your career?

I wouldn’t say this has been a challenge, but rather a change to my own approach to work. As someone who naturally leans into responsibility, I often find myself equating “wanting more” with “doing more”. As a vice president and client lead, my role includes the investment of time coaching and developing my team to provide them with the knowledge and tools to perform their roles effectively and progress.

This taught me an important leadership lesson: progress at this stage of my career is less about personal output and more about enabling collective success. By trusting my team, setting clearer boundaries, and prioritising development over constantly “doing”, I hope I have been able to grow into a more thoughtful leader.

In what ways have you tried to push innovation or rethink traditional approaches within your sector, and what impact has that had on your team or organisation?

Each year at GCM we set some strategic initiatives for the next 12 months. Last year my focus was our approach to client board meetings and how we can improve our process and the information presented to our captive boards to allow them to assimilate key pieces of information and better execute their fiduciary and governance responsibilities. We received some really positive feedback from clients and prospective clients in relation to the changes we made, and I am excited to see how we can continue to use technology to improve this process over the next couple of years.

I’m particularly passionate about helping develop the next generation of female leaders, creating space for others to step forward just as I’ve been encouraged to.

How do you see your role evolving over the next three to five years, and what initiatives are you most excited to pursue as you continue to grow professionally?

Over this period, I hope to see my role evolve to include a deeper involvement in the Cayman captive industry through contributions to IMAC and as a coach and mentor within GCM. I’m particularly passionate about helping develop the next generation of female leaders, creating space for others to step forward just as I’ve been encouraged to.

Many of the FORTY Under 40 winners are recognised for both business success and broader impact – how do you balance professional excellence with contributions to your community or industry landscape?

I was listening to a podcast recently where the guest said: “You do not have to justify all of your time by your productivity or by what you produce.” As both an ambitious professional and a parent, the reality that balancing excellence at work, contributing to the industry and being present for my family requires constant adjustment.

I wouldn’t say I always manage to get this right. What helps me find balance is acknowledging my limitations, setting boundaries and being intentional about where my energy goes each day, week, or month.

I have a genuine passion for the captive industry, particularly supporting the continued growth of the Cayman market and contributing to conversations that move our industry forward. I’m also deeply committed to inspiring the next generation of female leaders, showing them that impact and ambition can coexist with real life.

I’m fortunate to work with an exceptional team at GCM who all are dedicated to achieving excellence. Our collaborative approach ensures we deliver excellence to clients while still ensuring we have time to contribute meaningfully to the Cayman community, captive industry and to recharge personally.

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