People Moves: Taylor Returns to Plymouth Rock Assurance as President and CEO

September 24, 2026

Boston-based Plymouth Rock Assurance Corp. named Chris Taylor as president and chief executive officer. He will lead Plymouth Rock’s Independent Agency Group, effective October 12.

Taylor brings personal lines leadership experience to the role, most recently as vice president and head of state management at The Hanover Insurance Group, where he had P&L responsibility for auto, home, and ancillary lines. In that role, he built and strengthened independent agency relationships, expanded the company’s portfolio, and led profitable countrywide growth. He helped bring several new products to market, including a successful high-net-worth offering.

Before joining The Hanover, Taylor worked at Plymouth Rock, where he helped lead the company’s entry into the New York and Pennsylvania auto insurance markets through the independent agency channel. He began his insurance career at The Hartford in product management.

“Independent agents have always been central to Plymouth Rock’s business, and Chris understands firsthand what it takes to build the strong, lasting partnerships that our business requires,” said Jim Stone, founder and chairman of the Plymouth Rock Group.

Plymouth Rock Assurance and Plymouth Rock brands together write and manage $2.5 billion in auto and home insurance premiums across Connecticut, Massachusetts, New Hampshire, New Jersey, New York and Pennsylvania.