Heather Masterson

Executive Advisor to Chief Executive Officer @Definity

Toronto, ON, CA
MOBILE NUMBERS
+91 *********19

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WORK HISTORY

Jan 2026 — Present

Executive Advisor to Chief Executive Officer @Definity

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Toronto, ON, CA

Executive Advisor to the President and CEO to assist with the transition and integration of Travelers Canada into Definity Insurance.

EDUCATION

1991 — 1992

Memorial University, Newfoundland and Labrador

Honours Bachelor of Education

1993 — 1996

Insurance Institute of Canada

CIP and FCIP Designations, Business Management

1987 — 1990

Dalhousie University

Bachelor of Arts, (including completion of the Foundation Year Program at the University of King's College)

SKILLS

Health InsuranceBrokersExcessStrategyEmployment Practices LiabilityLiability AnalysisDisability InsuranceCommercial InsuranceCasualty InsuranceRisk ManagementLeadershipWorkers CompensationLegal LiabilityInland MarineProfessional LiabilityD&OUnderwritingLiabilityFinancial RiskReinsuranceCasualtyBusiness DevelopmentCommercial LinesInsuranceClaimPortfolio ManagementClaims ManagementManagementDirectors and Officers Liability InsuranceGeneral InsuranceTrainingNew Business DevelopmentNegotiationEmployee BenefitsUmbrella InsuranceProperty & Casualty InsuranceBusiness PlanningWorking with Brokers

ABOUT HEATHER MASTERSON

With the sale of Travelers Canada, Heather is supporting the transition as the Executive Advisor to the President and CEO of Definity. Prior to, Heather was the President and Chief Executive Officer for Travelers Canada, responsible for setting the strategic direction as well as delivering on financial and operational excellence for the Canadian organization. In her role Heather, focused on creating a highly engaged culture as Travelers Canada underwent a transformational journey to enable an exceptional broker experience, embrace an optimal customer experience and create an enhanced employee experience. Heather started her career at Travelers Canada as the Chief Operating Officer. In this role she was responsible for providing leadership and direction for Travelers Canada as well as overall strategic and operational leadership for eight different business units and functional areas. She had accountability for shaping strategy and driving execution, while ensuring exceptional broker and customer experiences. Heather joined Travelers Canada in September 2015 from Totten Insurance Group where she served as President and CEO. Heather is the Past Chair of the Insurance Bureau of Canada as well as the Insurance Institute of Canada Board of Governors. She also serves as a Board Member for Équité, and is a past Board Director of GISA and PACICC. Heather was named on the Global Business Insurance Top 100 list in 2020, 2021 and 2023. Heather was the recipient of the Insurance Business of Canada’s Woman of Distinction Award in 2018. She was a recipient of the Hub International Chairman’s Award for 2014 and an honouree of the 2013 Business Insurance Women to Watch Award. She was an inaugural member of the Canadian Chapter of the Insurance Supper Club, and is a global Ambassador - an executive insurance forum for women. She is a past member of the Board of Directors for the Women’s Brain Health Initiative. Specialties- Business and Operational Strategy- Contract Negotiations- Distribution, Sales and Marketing - Global Insurance Placements for Multi-national P&C Clients- Risk Management, Large Complex Commercial Business, Small Package Policy Segments

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Heather Masterson — Executive Advisor to Chief Executive Officer at Definity in Toronto, ON, CA | Unifers