Women in Hamilton: Gail McLeod

The Aon property broker was inspired to join the re/insurance industry by her first mentor - her mother. 

Gail McLeod's first mentor was also her mother, who joined the insurance industry as a receptionist and rose to be head of the property division in the same company. 

McLeod, a wholesale property broker at Aon, was nominated by a colleague who said: "Gail is one of the most organised and best planned individuals in the market. 

"She has significant relationships that go far beyond our shores, and in a relatively short period of time in Bermuda she has built a reputation as a dealmaker who can cut through the weeds to focus on the issue at hand."

Give us a snapshot of your career to date. 

I started my insurance career as a workers' compensation claims adjuster in my home town of Chicago, but after two and a half years I was ready to make a change and moved to retail property insurance broking at Aon in New York.  For fourteen years I worked in New York City – eight of those as a retail property broker at Aon, three as a retail property broker at Marsh.  I also spent a few years on the facultative reinsurance side for Aon.  Our family moved to Bermuda in 2021 and I started as a wholesale property broker in the Aon team. 

What attracted you to re/insurance? 

Like many people, it runs in the family! My mother was a property insurance underwriter so it was part of my day to day life growing up and my Mom always seemed to enjoy her work. After graduating from college with a business degree it seemed like a natural fit. 

Who inspired you or acted as a mentor in your career?

I’ve had several mentors in my career. First and foremost my Mother. She ran a property division in the company she joined as a receptionist in the 70’s before many women had senior roles. Jackie Bolig, who now runs North American P&C at Willis, ran the team I joined when I first started in New York and she has been an incredible role model. 

What are your ambitions?  

I have a real love for property insurance, both the people and the transactional side of the business.  I've been incredibly lucky to have worked at two dynamic companies in various groups that have both been educational in the property space.  Being somewhat new to the Bermudian property marketplace, I am driven by a desire to continue to grow professionally, expand my network, and continue to thoroughly enjoy what I do every day.

Do you feel the re/insurance industry has made progress in terms of diversity and inclusion since you entered it?  

Definitely. When I first started in the industry in 2004, it was overwhelmingly male-dominated. Fast forward 20 years and the teams I’ve been lucky enough to be a part of are much more diverse in all aspects and I have worked with some really amazing female leaders. It’s not perfect, and there is always room for improvement, but it’s come a long way from when I started and certainly leaps and bounds from what our industry looked like in the 1980s and 1990s. But like most industries there always remains room for improvement.

Do you feel this sector is especially attuned to diversity and inclusion?

It’s getting better and is now part of the conversation. Certainly at Aon there has been a real culture change from the top down that highlights and celebrates diversity and inclusion.  We now have committees around the world that work to champion this and make sure it is front and centre for our high level decision makers.

Is there anything you would like to improve or change?  

I think that for anyone in any role there are many things that you would like to see be done differently. What I think is important is that you have a voice in any change and that an individual’s concerns are taken seriously. 

Have you encountered any challenges related to diversity and inclusion?  

Yes. In the 20 years that I have worked in insurance I have come up against challenges, most of them due to being a female in a male dominated work environment.  This is not to say that I have never worked with men that have championed and promoted me as a team member, but that as a woman in this business I do feel that you have to pedal harder and shout a bit louder in order to be visible.

Would you encourage other women to consider this sector?

I would.  The re/insurance sector is full of opportunities in various disciplines – broking, underwriting, analytics, that all cater to various career paths.  I personally have found that after Covid, working from home and work life balance has improved so it's easier for women to navigate a professional career while also meeting familial needs.

Why is this industry great to work in?  

This industry is a great place to work as it’s challenging but remains a people business.  You can make this business what you want it to be.  I moved to New York City from Chicago in 2007 and didn’t know anyone in the city and through my colleagues I’ve made lifelong friends. Our industry is everywhere – it can provide opportunities to travel and work in other cities. You get to meet and work with colleagues in different countries. If you like to work with people it's a great business! 

Why is Bermuda a great place to be?  

Bermuda is a dynamic hub for re/insurance.  For a small island, one is much closer to all aspects of our industry from insurance through retro and all the analytics in between with access to key decision makers. Not to mention … the commute is pretty nice!

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