Industry veteran Heather Masterson announces next role

Canadian property and casualty insurance industry veteran Heather Masterson has announced she will be stepping into the role of president and CEO of Équité Association in September.

Masterson says she spent an “incredibly rewarding” decade as president and CEO of Travelers Canada. Most recently, she served as executive advisor to the president and CEO of Definity Financial Corporation, Rowan Saunders.

In May 2025, Definity entered into a $3.3-billion merger agreement to acquire Travelers’ Canadian business, adding about $1 billion of personal insurance business to its portfolio. The deal closed in January and makes Definity a Top 5 P&C insurer in Canada. Saunders said in an earnings call in February Definity is aspiring to become a Top 3 insurer in Canada.

“It has been a true privilege to work alongside one of the best teams in our industry,” Masterson says in a LinkedIn post Thursday. “Together, we built a high-performing organization grounded in a strong culture of care, accountability, and excellence. I am deeply proud of what we accomplished and confident in the team’s continued success at Definity.”

Following the Definity-Travelers transaction, Masterson says she took on a short-term advisory role to support the transition and ensure her team was well-positioned.

“With that work now complete, the timing feels right to step forward,” she writes. “This summer, I’ll be taking time to focus on family — something that has always been a core priority for me.”

On Sept. 8, 2026, Masterson will step into the role of president and CEO of Équité Association. The industry association’s mandate is to prevent insurance fraud and crime.

“I would also like to recognize Terri O’Brien for her outstanding leadership and contributions to our industry,” Masterson says, referring to the current president and CEO of Équité.

“To my colleagues at Travelers Canada and Definity — thank you,” Masterson writes in her LinkedIn post. “It has been a privilege to lead and to work alongside you. I will be cheering you on every step of the way. Here’s to the next chapter.”

Current Équité leader to retire

Équité Association tells Canadian Underwriter that O’Brien announced her intention to retire late last year and the association is pleased to welcome Masterson as its next president and CEO.

“Heather brings over three decades of leadership experience in the Canadian P&C insurance industry…,” Équité says. “Her strategic vision, operational acumen, and deep commitment to the Canadian insurance sector are well-established.”

Masterson is a founding and current member of Équité’s board of directors, where she has developed “deep knowledge of the association, its mandate, and our strategic priorities,” Équité tells CU. “She arrives not to learn the association, but to lead it, with a clear focus on continued growth of our mission and mandate.”

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Adds O’Brien: “I have every confidence that Équité is well-positioned for continued success under Heather’s leadership, and I am committed to a thoughtful transition so that the strategic priorities we have built together continue with momentum and purpose.”

Masterson started her career with Travelers Canada as chief operating officer. Before that, she was president and CEO of Totten Insurance Group. She’s also had roles at Hub, AIG, and other insurers.

Masterson has extensive industry experience, including past roles as chair of the Insurance Bureau of Canada and chair of the Insurance Institute of Canada’s board of governors. She is also a past board director of the General Insurance Statistical Agency and the Property and Casualty Insurance Compensation Corporation.

Jason Contant

Jason has been an award-winning journalist with Canadian Underwriter for more than a decade, including the past three years as associate editor and, before that, as digital editor for seven years.