Plymouth Rock Assurance News

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Plymouth Rock Sells Encharter Agency to MountainOne

Oct 22 2026 // Plymouth Rock Assurance Co. has sold a western Massachusetts independent agency it bought more than 25 years ago. The buyer, MountainOne Insurance Agency, is owned by regional bank MountainOne Bank. The sale of...

People Moves: Plymouth Rock Home Names Stuckey VP of Customer Service

Oct 1 2026 // Jared Stuckey Plymouth Rock Home Assurance Corp. headquartered in Boston, Massachusetts, named Jared Stuckey as vice president of customer service and underwriting. Stuckey previously led underwriting strategy and managed...

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

Sep 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...

People Moves: Plymouth Rock Names 3 Key Leaders; Valekha to Lead MIA Financial Unit

Aug 5 2026 // Plymouth Rock Assurance Makes Leadership Appointments Plymouth Rock Assurance, headquartered in Boston, Massachusetts, appointed Gavin McPhail as vice president and chief data officer; Cornelius Young as vice president and...

Plymouth Rock Launches ChatGPT for Home Insurance Quotes

Aug 3 2026 // Homeowners can now obtain insurance quotes from Plymouth Rock Home Assurance through a “natural” conversation with ChatGPT, the artificial intelligence chatbot created by OpenAI. The insurer claims it creates a...

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