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Kevin O'Leary started their work experience in 1982 at Dominion of Canada, where they held various roles including Field Representative and Senior Underwriter. Kevin excelled in broker and staff relations while achieving significant growth and mutual profitability. In 1994, they joined Northbridge Insurance as a Director, Executive Underwriter, Manager, Team Lead, Senior Underwriter, and Underwriter. Specific details about their role at Northbridge Insurance are not provided.

Kevin O'Leary has obtained a CIP (Chartered Insurance Professional) certification from the Insurance Institute of Canada. Kevin has also pursued a field of study in P&C Insurance at the Insurance Institute of Canada.