Rising Star: Jillian Benson
Jillian Benson, as group head of reporting at Fidelis Insurance Group, played a key role in the company’s IPO and continues to lead SEC reporting and support investor communications.
She is a chartered professional accountant with a background in auditing, financial analysis and controllership. Based in Bermuda, Benson is driving innovation in financial reporting by championing technology and cross-functional collaboration. Her work is helping shape the future of finance at Fidelis and her impact is recognised across the industry.
Can you start by telling us what inspired your career?
Let’s face it, there is nothing particularly exciting about becoming an accountant. When I was in high school in Canada, a former student returned to speak about her life as an accountant living in Bermuda. That caught my attention. She handed out a sheet titled ‘How to become an accountant and move to Bermuda.’ I kept it like a blueprint and followed the steps almost exactly.
The blueprint didn’t include instructions for finding a partner willing to move, or later convincing family to join, but I managed that, too!
While accounting might not sound thrilling, it has been a passport to an extraordinary life.
What elements of your career do you enjoy most and why?
It has to be the people. Unlike industries that produce tangible goods, the re/insurance sector is built on relationships. It’s a people-based business and success depends on collaboration, trust and creativity.
Challenges are inevitable, but what truly differentiates success is the people you work with. I love building strong relationships, both across internal teams and with external partners. Working closely with others to find solutions and drive progress is incredibly rewarding.
I also take great satisfaction in streamlining processes and improving systems. I am always looking for ways to help our teams work more effectively together and deliver greater value.
Can you share an example of a challenge you overcame that significantly shaped your career trajectory?
M&A is inevitable in this industry. I’ve been on both sides, and each brought growth and change, though not without challenges. These moments force you to reassess, adapt and evolve. My approach has been to embrace those shifts and ask: “How do I come out stronger?”
On a personal level, becoming a mother brought a transformative shift. My journey to motherhood was challenging, and when it finally happened, everything changed. Suddenly, I didn’t have the flexibility to work endless hours. That forced a powerful realisation that just because you can do everything does not mean you should.
I became laser-focused on where I could add value. It changed how I work, prioritise and define success. Every minute at work is now intentional. I’ve learned to focus my energy where my time and skills matter most.
This new season of my career is defined by clarity, purpose and a fresh perspective.
What are your career ambitions? And how will you work to achieve them?
My ambitions have always evolved depending on the season I’m in – both professionally and personally. Right now, I’m in a season of balance. I’m focused on doing what I do well, delivering value and being fully present in my role.
I joined Fidelis to support its IPO in 2023 and help grow the company as a publicly traded business. That meant stepping back from chasing traditional ambition and focusing on something more meaningful – being part of a team that is building something long-lasting.
It has been incredibly rewarding to contribute to the Fidelis story. I help navigate regulatory requirements, support our shareholders and help shape the company’s future.
My goals are less about climbing a ladder and more about showing up with purpose. Sometimes ambition means saying yes to new challenges, other times it’s knowing where you can make the biggest impact and leaning into that. Right now, I’m doing the latter with intention and focus.
How do you stay motivated and continue to learn in such a dynamic sector?
I’ve always loved learning, so staying motivated has never been the issue. Finding the time is.
This industry moves quickly, and keeping up requires intention. I surround myself with smart, curious people, ask the right questions and never assume I know all the answers.
One of the best things about being in Bermuda is the strong sense of community. It is easy to stay connected with peers who are navigating similar challenges. The environment here really encourages knowledge sharing, and that is invaluable. Those conversations help me stay sharp and engaged.
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