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Bill O'Sullivan has held various roles throughout their work experience. Bill started their career at The Andy Ross Group as a Professional Mortgage Planner, where they achieved the top production for the 2006 calendar year. Bill then joined Farmers Insurance as a Senior Field Territory Manager, where they focused on growing agency business and exchanging selling strategies. Bill later joined Travelers as a Sales Executive, where they reshaped an underperforming territory and improved renewal retention. Bill then moved to The Hanover Insurance Group as a Territory Sales Manager, responsible for driving the strategic development of partner agents and achieving profitable growth. Bill's next position was at Preferred Mutual as a Field Sales Leader, where they led a sales and distribution team and managed new business growth and written premium retention. Bill then joined Renaissance Alliance as the Director of Agency Recruitment before taking on their current role as the Director of Sales National Account at Embark General.

Bill O'Sullivan attended Roger Williams University from 1995 to 1999, where they obtained a Bachelor of Arts (B.A.) degree in Corporate Communications. In 2016, they also obtained a certification as a Licensed Massachusetts Property & Casualty Producer from the State of Massachusetts.