Heather Masterson (pictured) is a well-known female figurehead in the Canadian insurance industry. As president and CEO of Travelers Canada, she frequently takes part in executive panels and is a familiar face and voice at industry events. Recently, she took part in a virtual Dive In festival fireside chat, where she lifted the lid on her career journey and some milestone moments in her family life. She also reflected on three key themes, which she claims have shaped who she is today: being resilient, having a growth mindset, and embracing the notion of emotional intelligence.
Masterson started her career in 1993 as a trainee underwriter working for an insurance company in Toronto. She gained hands-on technical training and development alongside a more formal education, and she soon received her first professional designation. Next, she took a job with a specialty insurance carrier, where she gained her second professional designation after diving deeper into the craft, spending time with the reinsurance community, and building a greater understanding of broker and customer relations. Her first two jobs were all about “building foundations,” she said.
In 1998, she moved from Toronto back to Newfoundland to work alongside her brothers and her father in the family insurance business. She reflected: “I was very excited to go home and be with my family […] but it was almost immediately that I recognized that being the daughter of the owner wasn’t going to be a piece of cake. In order to have the respect of the people around me, I was going to have to buckle down, work hard, be focused, earn the respect and the credentialing that I was seeking, and gain credibility. That’s a lesson I’ve taken with me for each and every new position I’ve entered into. You have to earn your stripes, and there’s no other way to do it other than rolling up your sleeves, creating value and earning people’s trust and respect.”
After a year of working in the family business, Masterson reached a major milestone. She got engaged to her boyfriend, and together they decided to move back to Toronto to start their married life and raise a family. She described that decision as “daunting” – not the getting married part – but the uprooting and the leaving of the family and the family business behind.
“It was around this time that I received some very good advice,” she said, “which was to invest back into the industry that you’re building your career in. I’d already started to teach insurance courses, and I decided that I was going to invest my time, effort and energy into the Insurance Institute of Canada. I started volunteering, serving on committees, on the Governing Council, and it’s been a terrific experience. I’ve met so many fantastic people who share common interests and a passion for education, and it’s something that I recommend you do. Find your cause and invest in it - give back.”
When Masterson returned to Toronto, she re-joined the specialty insurance carrier she was with prior to leaving and she took on the role of head of distribution. She had to learn a brand-new skillset around influencing, honing her negotiation skills, and getting senior people together to collaborate and create value for the broader organization.
“It was definitely a stretch role,” she commented. “It was an opportunity for growth and expansion, both in skillset and mindset. And I really enjoyed that challenge. It teed me up and got me ready for my next opportunity, which was running P&Ls on my own. It also taught me how to be a better leader and a better manager.”
It was soon after this that Masterson faced another life milestone – she became a mother. Motherhood changed her perspective. She described it as “the turning point” in which she evolved from being a “textbook manager” to being a more “authentic manager” – one who understood the positive impact she could have on others, while also acknowledging (with two young daughters at home) that the work-life balance can sometimes feel like a stretch.
Her next role was with one of the largest insurance brokerages in the Canadian market. Here, she learned a lot about distribution, but the lesson that really stood out came from the culture of the organization – it was around how to celebrate success, and how to give and receive compliments. When Masterson gained her first executive oversight role in 2012, becoming president and CEO of a large MGA in the Canadian market, she took that lesson with her and ensured that everybody in her organization had a voice.
“The first thing I did was meet with every individual in the organization and ask the same three questions to everybody, so I could gather data and understand how everyone was thinking, what their expectations were, and how they aligned with my thoughts around the planning that needed to be done,” she reflected. “It’s important to understand that everybody has a voice, and the importance of listening to people, and the whole notion that you need to stay really close to your front line, because your front line really knows what’s going on in the organization.”
In 2015, Masterson joined The Travelers Group of Companies, and she was appointed president and CEO of the P&C insurance giant’s Canada operations in 2016. Thinking about resiliency, the growth mindset and emotional intelligence in her current role, she said: “I’ve been able to continue to build resiliency (now it’s more executive resiliency). My growth mindset work is now transformed into teaching others about the importance of growth mindset, the ability to adapt to change and to be resilient to change. And, of course, from an emotional intelligence perspective, it’s how to have a higher level of engagement within the organization, which leads to more satisfaction within one’s job and their role, and better productivity across the organization. It has been a phenomenal journey - one that’s not over - but one that I’ve certainly enjoyed to date.”
