Women in Hamilton: Michelle Bailey, AXA XL
Insurance companies in Bermuda are more open to discussions on diversity and inclusion, though there’s still work to be done, says the Head of Professional, at AXA XL in Bermuda.
Michelle Bailey is Head of Professional, Bermuda, for AXA XL. She began her career at AXA XL a year after graduating from university. Initially, she worked as a technical assistant in the professional liability department. From there, Bailey climbed the ranks while training summer students and junior colleagues. She did a secondment in the UK during the early part of her career, but Bermuda was where her heart lay.
Today, she works with the next generation of exceptional underwriters - a role that continues to inspire her.
What attracted you to insurance in the first place?
Initially, I was an economics major at university, but an introduction to risk management class changed everything. I loved the blend of business, law and risk. I switched majors to risk management, insurance and actuarial science, and earned a dual degree in finance. This combination wasn’t as common in the 1990s, and it gave me an edge when I returned to Bermuda, where insurance is a bedrock of the economy. It felt like a natural choice.
Is there someone–or some people–who inspired you or acted as a mentor in your career?
Over the years, I’ve had the privilege of being trained and mentored by an exceptional co-hort - Patrick Tannock, Sherron Williams, Bill Wharton and Matt Irvine. This was a tremendous opportunity for me. These people are widely regarded as some of the best in the industry – basically the “avengers of underwriting”. Today I hold the position of Head of Professional which is a great honor and I get to work alongside the next generation of avengers.
“I’m deeply invested in nurturing the next generation of underwriters. I strive to create an environment where diverse perspectives are valued, and fresh ideas celebrated.”
I've learned so much by just observing and interacting with a variety of talented colleagues who helped shape my perspective on what true professionalism looks like.
What are your ambitions for the future?
My primary ambition is to leave things better than I found them. Bermuda has always been at the forefront of innovation, and I want to help our clients tackle complex risks by developing cutting-edge insurance solutions.
Additionally, I’m deeply invested in nurturing the next generation of underwriters. I strive to create an environment where diverse perspectives are valued, and fresh ideas celebrated. It’s vital to build a team that reflects the diverse nature of our clients and one where they can see a clear pathway to leadership.
What would you say is your greatest achievement?
Watching the next generation step into senior roles and excel in their careers makes me incredibly proud. Some of these individuals don’t fit the traditional mould – some don’t even have degrees – but they excel through talent and hard work. Being a part of their journey is immensely rewarding.
Has the industry made progress in diversity and inclusion since you began?
Definitely, though there’s still work to be done. When I started in the early 2000s, I was often one of the few women of colour – sometimes the only one – in the room. However, at AXA XL, the seat that I hold today as Head of the Professional Lines department was held by a Black woman 20 years ago, so I always knew and felt it was attainable. Outside of AXA XL in Bermuda and overseas it was clear to me how unique of a culture we had here at AXA XL in Bermuda. As an industry, have we made progress? Absolutely. Is there more work to be done? Yes. As Patrick Tannock would say, we can acknowledge the progress that’s been made and still admit the tremendous work that still needs to be done. This is particularly true at the C-suite and board levels.
Is there anything you would like to improve or change?
In addition to levelling the playing field at senior ranks, especially the C-suite and board levels, where diversity still lags, I’d like to see us lead in accelerating knowledge and innovation around artificial intelligence. While diversity at the underwriter and middle-management levels has been shown to drive both morale and financial benefits, we still have work to do at the top.
What challenges have you faced in your career, and how did you overcome them?
Balancing single motherhood with climbing the corporate ladder was tough. I leaned on a strong network of family and friends and learned to ask for help. Another challenge was navigating rooms where I was the only one who looked like me. I let my work speak for itself and committed to being excellent. Social settings were tricky at first, but I found my stride by being authentic and steering conversations into areas where I could connect.
Would you encourage other women to consider a career in insurance?
Without a doubt. This industry offers opportunities to engage with Fortune 1000 leaders and tackle intellectually stimulating challenges. It’s financially rewarding and ever-evolving, especially with roles in AI and cybersecurity opening up.
Why is this industry a great one to work in?
Our industry touches nearly every sector of the economy, and so no two days are alike. Working in the insurance industry, which is relationship driven and at the forefront of global trends, is highly rewarding and incredibly diverse; beyond underwriting and claims, there are roles in communications, finance, marketing and more. Plus, the industry’s constant evolution – with new risks and technologies – keeps it even more interesting.
Why is Bermuda a great place to live and work?
Bermuda’s insurance community is uniquely collaborative. Competitors come together at industry events, creating a collective wisdom that benefits everyone. Clients often remark on the insightful questions and expertise they encounter here. And let’s not forget – it’s paradise!
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