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Heather Masterson

Totten Insurance Group

Heather Masterson

President and CEO
Totten Insurance Group
Age: 43


While insurance runs in Heather Masterson's blood, it wasn't always a foregone conclusion that she would take up the family business. Yet, her yearning to solve problems and make a difference has led to the corner office at Toronto-based Totten Insurance Group, a wholesale division of Hub International Ltd. that provides solutions for hard-to-place property/casualty accounts. After a long and varied career at American International Group Inc., Ms. Masterson arrived at Hub in 2009 and took over at Totten in 2012, and is now responsible for overseeing the company's six offices in Canada.


What's your advice for women entering this field?

When you look at your career, know that it is going to be a long runway. You will have ebbs and flows. You may have times where you are looking for extra education or to start a family, where you need to remember that you are in it for the long haul. Another piece of advice that I have is not just for women: you need to be fair. Once you are recognized for being fair, there is a degree of respect that will flow from that. However, while it's important for you to be fair, don't always expect life or business to be fair. This allows you to not be emotional and allows it to be just about the business.


What attracted you to this industry?

I grew up in a family that was insurance-related. My father owned numerous insurance businesses, including a brokerage, a premium financing company and, finally, a claims adjusting firm. So, I was in and out of his office while growing up doing various jobs. I did it all. If he needed somebody to come in and shred files, I was churning files. But I never thought I would end up in insurance. I earned a teaching degree but thought at the time that I would not be a teacher, but that it might help me in whatever field I ended up in. So, I landed in insurance to some extent by default. Out of four children, three of us are in insurance.


What aspects of your job give you the greatest sense of accomplishment?

I love problem solving. I love that insurance is about providing solutions. When you can come up with a win-win resolution for a complicated problem, you had to work through and have a satisfied customer in the end. I get a natural high from that. Another part that I enjoy is that insurance is still a people business. The more advanced we get about technology and finance, the better we get about contract clarity and the legal component. The basic fundamental principles of insurance are about providing for a basic need of people. That suits my personality well.


What's the most important lesson you've learned in your career?

There are no shortcuts. Take the time, put in the effort and do your due diligence.


What's at the top of your bucket list and why?

The most important thing in my world is being happy. So the top of my bucket list is to live my life in a reasonable state of happiness. I want to do the right things and engage in the right activities and be productive for the folks around me. I am also the mother of the two young girls, so it's high on my bucket list to be a good example to them and that they grow up in a house where they know they are loved.


What's your secret vice?

That's a no-brainer. My guilty pleasure is wine. I don't discriminate in red, white or even champagne.


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