Heather Masterson

President and CEO, Travelers

Heather Masterson is the President and CEO for Travelers Canada. In this role, she is focused on three corporate priorities: financial and operational excellencecustomer centricity and broker experienceand employee engagement. She is equally committed to identifying opportunities to continue leveraging the company’s deep competitive advantages to best serve brokers and customers across the country. 

Heather joined Travelers Canada in September 2015 as Chief Operating Officer, bringing her knowledge of the Canadian marketplace and broker community to the company’s operational, service, and distribution strategies. 

Before joining Travelers Canada, Heather was the President and CEO of the Totten Insurance Group (TIG). There she was responsible for providing leadership and direction for Totten Group, and for managing the profitability of the company as well as its partner insurance carriers.  

With more than 20 years of insurance experience, Heather has held number of executive roles over her careerPrior to Totten, she was an executive at Hub International (the tenth largest insurance broker worldwide), where she was Chief Marketing Officer and Executive Vice President of Risk Management and International Client Services. Heather was also the Vice President of AIG Worldsource — a division she built from the ground up to $50 million, in just seven years. A graduate of both Dalhousie University and Memorial University, Heather also holds a FCIP in Management from the Insurance Institute. She is a Senior Vice President of the Insurance Institute of Ontario’s Governing Council, a recipient of the Hub International Chairman’s Award for 2014, and an honouree of the 2013 Business Insurance Women to Watch award. She is a member of the Board of Directors of the Women’s Brain Health Initiative and is actively involved in The Insurance Supper Club — an executive insurance forum for women. Previously, she was an active member of the Executive Women in Insurance Networks (EWIN) Board of Directors. 

Heather lives in Toronto with her husband and their two daughters.