Mary Boyd

Mary Boyd

CEO & President, Plymouth Rock Assurance

Mary Boyd is a seasoned senior executive with over 25 years of applying her diverse set of skills to leading businesses through transformative phases in their history that span invention, renovation, integration and rebuilding. Mary’s career reflects a strong track record of translating strategic vision into reality, evident as she leads organizations tackling operations, technology and team transformation. She brings innovation and an agility of approach that explain her successes in both seeing the forest and navigating the trees by spotting the strategic opportunities in the space between them.  


As the President and Chief Executive Officer of Plymouth Rock Assurance Corporation, Mary has financial responsibility for their nearly $900M Independent Agency Auto, Pilgrim services, and Umbrella liability business. Readying her growing business for sustained success, Mary is currently guiding her team through a multi-discipline digital evolution of their business that connects product, customer and agency partner digital experiences across the customer life-cycle.  

Since 2006, Mary has held President and division leadership roles; reliably improving net income in each case by maximizing channel economics, applying her commitment to best-in-class partnership management, and advancing operational excellence.  

She joined Plymouth Rock in 2018, from The Hartford, where she held the position of Senior Vice President with responsibility for both their Agency and Direct channels personal insurance businesses. Prior to that, Mary invested 15 years of her career in high net worth personal lines, beginning her tenure at Chubb as an actuarial trainee and expanding to roles of increasing responsibility; most recently as President of their Private Risk Services division. Mary is the Insurance Library Association of Boston’s 2022 Insurance Professional of the Year, an honor she received in August.  

Mary received her bachelor’s degrees in Applied Mathematics and Economics from Rutgers University. 


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