Heather Masterson | Travelers Canada

Heather Masterson, President, CEO, Travelers Canada

Heather Masterson’s journey into property and casualty insurance began in the heart of St. John’s, Newfoundland, when she was inspired at an early age by her father’s dedication to the industry and his passion for being an insurance broker.

Her father’s influence and mentorship shaped her understanding and recognition of the critical role insurance plays in people’s lives, “from safeguarding that which matters most to people, to being there to support and take care of our customers when the unimaginable happens,” she says.

Today, Masterson says she’s proud to be a part of the insurance industry. She’s also honoured to be a CEO and lead 1,400 colleagues across Travelers Canada.

“I especially appreciate the incredible mentors and advisors who have shared their valuable time and insights, helped groom and prepare me for leadership and provided invaluable feedback along the way,” she says. “Surrounding yourself with people who support growth and development at every stage in your career has never been more important when you consider the transformation our industry is going through.”

In her roles as both CEO and chairwoman of the Insurance Bureau of Canada, Masterson says she feels privileged to contribute diverse ideas and perspectives garnered from her varied experiences. She has worked in the brokerage, insurer and MGA business segments, and has been involved in various other trade associations and volunteerism throughout her career.

Masterson’s leadership philosophy is deeply-rooted in servant leadership, prioritizing the well-being and success of her team. By supporting her colleagues, creating a culture of caring, ensuring everyone is aligned on the priorities, and empowering team members to be their best, Masterson believes Travelers Canada is well- positioned to create a positive impact on the industry and the communities it serves.

She reflects on her path to leadership with gratitude for the opportunities that guided her there. But she admits the road hasn’t always been smooth.

“As a woman in leadership, I often think about career growth opportunities and the barriers we face, especially in our leadership ambitions,” she says. “In my career, I’ve experienced some of the most frustrating assumptions around maternal bias. And I think every woman has felt underestimated at some point in her career.

“I overcame my barriers by ignoring bad advice and being brave enough to speak up for myself. I invested in my professional development, which was especially important early in my career when my experience was limited. I worked all day, then studied in the evenings to complete my CIP, then FCIP. It sent a message I was serious. Resilience is also fundamental to navigating the inevitable career challenges you’ll face. You build resilience by developing an effective network, becoming a life-long learner, keeping an optimistic mindset, and looking at setbacks as learning opportunities.”

She encourages women to establish their core values early on, build their brand, develop diverse skill sets, create networks, seek out mentorship, and volunteer within the industry. “Don’t try to do it all at once,” she says. “Your runway is long, so take the time to invest in your career thoughtfully. Build out your capabilities as well as your capacity to do more and to take on bigger roles over time.”

Despite the progress made, Masterson acknowledges women are still underrepresented in senior leadership roles within the insurance industry.

Her efforts to advocate for and empower women in the industry – she is Global Ambassador for The Insurance Supper Club, boasts multiple awards for her contributions as a distinguished female insurance leader, and has a senior leadership team that is 50% women – reflect a broader call to action for a more proactive approach to paving the way for female leaders.

“It starts with bias-aware recruitment practices, building a diverse pipeline of high performers, offering comprehensive diversity and inclusion strategies, and promoting a positive and inclusive culture,” Masterson says. “At Travelers Canada, we have worked hard to build our senior female pipeline and support women’s advancement through training, professional development, career-pathing and mentorship. We’re committed to fostering our culture of caring, where every employee feels supported, valued and respected, and this is underscored by our Travelers Promise to take care of our customers, communities and each other.”

She believes the industry needs to do more to encourage women to join the industry, especially in underrepresented roles such as IT, claims investigators, appraisers, and commercial and specialty brokers.

“We’ll achieve this by hosting more talent summits, creating accessible networks, and by telling our story – a story that is compelling because we are sharing the value proposition of insurance as an exciting career full of opportunities for women.”