Rising Star: Jotessa Musson

Jotessa Musson began in audit at a big-four firm, then moved into insurance broking, which ultimately led to her present position as property reinsurance underwriter II at Everest.

While her career path has not been linear, each step has been instrumental in building the foundation for her current responsibilities, including analysing complex risks, structuring innovative solutions and managing key client and broker relationships.

Can you start by telling us what inspired your career?

Growing up in Bermuda, I was surrounded by the influence of the re/insurance industry, witnessing its impact on our local economy and community. Inspired by my determined family, I set a clear goal early on: to build a career to provide for my loved ones while making a positive contribution.

I was incredibly fortunate to have mentors, including my aunts – a successful accountant and a lawyer – who saw that spark in me. They taught me that being told “no” is simply a prompt to find another way and turned my ambition into action through work-shadowing experiences.

I found myself captivated by the energy in the boardrooms, the intellectual rigour of solving problems and the satisfaction of meeting deadlines. I saw a career that offered global connections, meaningful challenges and a chance to make a tangible difference.

What elements of your career do you enjoy most and why?

I can honestly say it’s a joy to come to work. Underwriting is anything but a static desk job! There is a dynamic energy to it that I thrive on – meeting with clients and brokers, delving into new and emerging risks and knowing every day brings a puzzle to solve.

I love how news can spark conversation on how we can innovate and improve our craft. This global dynamism led directly to one of the most formative experiences of my career by giving me the opportunity to be seconded to the Everest London office. This experience pushed me far beyond my comfort zone. It taught me to see challenges through a different lens and forced a new level of personal and professional growth.

This industry gives me profound fulfilment. The work we do is not just about policies and premiums; it is about providing a backstop that allows society to function and innovate. Knowing our efforts directly help communities recover and rebuild is a powerful motivator and the reason I am so passionate about what I do.

Can you share an example of a challenge you overcame that significantly shaped your career trajectory?

The most rewarding career paths are rarely linear, and my own is testament to that. My career began in audit, an experience I value for the immense discipline and analytical rigour it provided. While working directly with insurance clients, I discovered my passion lay not in reviewing the past, but in shaping the future of risk.

This lesson was the springboard for my transition into insurance broking. The broking world was transformative, offering a front-row seat to the dynamics of the insurance market. I refined the art of negotiation, learned the importance of building and nurturing relationships and significantly grew my professional confidence. This combination of skills and experiences provided the perfect preparation for the demands of my current underwriting role.

What are your career ambitions? And how will you work to achieve them?

I am focused on meaningful growth in my underwriting career by defining advancement not by job titles, but by value delivered. It’s about embracing new opportunities as a chance to learn and continuing to challenge myself without fear of failure.

I’m eager to take on more complex risks and have a voice in the conversations that drive our business forward. I aspire to one day lead a team and mentor the next generation, continuing the cycle of guidance that has been so critical to my own success.

How do you stay motivated and continue to learn in such a dynamic sector?

Staying motivated is easy. Joining the industry during a hard market was a baptism by fire in the best way possible. Rates were high, terms were being pushed and, as underwriters, we had to be sharp, disciplined and resilient, making the experience invaluable for my development.

In many ways, navigating future challenges brings me back to the inspiration of my early years in Bermuda. The belief that “if it’s to be, it’s up to me” has always been my constant guide – a principle that has not only shaped my past but will continue to define my future.

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