Plymouth Rock Assurance sells auto, home, renters, and condo insurance in the Northeast through employees and independent agents. Policies are underwritten and supported by claims and service teams with offices in Woodbridge, NJ and Boston, MA serving NJ, NY, NH, MA, CT, and PA. Customers access coverage through an agent network and in-house teams who match needs with appropriate policy options. The company differentiates itself with strong community involvement, recognized workplace culture, and a focus on reliable, high-quality service for families and communities.
Company Size
1,001-5,000
Company Stage
N/A
Total Funding
N/A
Headquarters
Boston, Massachusetts
Founded
1983
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Plymouth Rock Home Assurance names Jared Stuckey VP of Customer Service and Underwriting. BOSTON - Sept. 29, 2026 - Plymouth Rock Home Assurance Corporation has named Jared Stuckey Vice President of Customer Service and Underwriting, effective immediately. Stuckey led underwriting strategy and managed personal and commercial products for Plymouth Rock's Independent Agent auto business. He will now oversee both customer service and underwriting for the Home Insurance group. "Jared gets things done," said Bill Martin, President and CEO of Plymouth Rock Home Assurance Corporation, announcing Jared's promotion. "In 20-plus years across nearly every insurer function, he's built a track record of results. Our officers universally identified him as our highest potential manager. We are thrilled to have him here on the Home team." Before joining Plymouth Rock, Stuckey spent 16 years at Liberty Mutual, where he held a variety of senior roles in product management and customer experience. He is a graduate of Goshen College and holds an MBA from The Wharton School. "I'm excited for the opportunity to use my experience in customer experience and home insurance at a time when so much is evolving," said Stuckey. "The opportunities to innovate and enhance the customer experience are tremendous. Our agents are going to love the changes to come." About Plymouth Rock Plymouth Rock was established to offer its customers a higher level of service and a more innovative set of products and features than they would expect from an insurance company. Plymouth Rock's innovative approach puts customers' convenience and satisfaction first, giving them the choice to do business the way they want - online, using a mobile device, by phone or with one of Plymouth Rock's agents. Plymouth Rock Assurance(R) and Plymouth Rock(R) are brand names and service marks used by separate underwriting, managed insurance, and management companies that offer property and casualty insurance in multiple states pursuant to licensing arrangements. Taken together, the companies write and manage $2.5 billion in auto and home insurance premiums across Connecticut, Massachusetts, New Hampshire, New Jersey, New York and Pennsylvania. Each underwriting and managed insurance company is a separate legal entity that is financially responsible only for its own insurance products. Actual coverage is subject to the language of the policy as issued. You can learn more about Plymouth Rock Company by visiting plymouthrock.com.
Plymouth Rock Assurance Corporation names Chris Taylor President and Chief Executive Officer. Industry veteran returns to Plymouth Rock to lead its Independent Agency Group's next chapter of growth. September 23, 2026 11:00 ET | Source: Plymouth Rock BOSTON, Sept. 23, 2026 (GLOBE NEWSWIRE) - Plymouth Rock Assurance Corporation today announced that it has named Chris Taylor as President and Chief Executive Officer. He will lead Plymouth Rock's Independent Agency Group, effective Monday, October 12, 2026. The appointment reflects Plymouth Rock's continued investment in the independent agency channel, backed by Taylor's decade-plus track record of personal lines insurance leadership and deep experience in the agency channel. "We are thrilled to welcome Chris into his new role," said Jim Stone, Founder and Chairman of the Plymouth Rock Group. "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." 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 been central to my career and to my view of how insurance is best delivered," said Taylor. "Agents know their clients, understand their communities and bring a level of personal guidance that is incredibly valuable to insurance shoppers. I'm excited to return to Plymouth Rock to work alongside a strong team and our agent partners, building on that strength and creating new opportunities to grow together." Taylor holds a BS in Chemistry from the University of Connecticut, an MS in Chemistry from the University of Illinois, and an MBA from the University of Connecticut. About Plymouth Rock Plymouth Rock was established to offer its customers a higher level of service and a more innovative set of products and features than they would expect from an insurance company. Plymouth Rock's innovative approach puts customers' convenience and satisfaction first, giving them the choice to do business the way they want - online, using a mobile device, by phone or with one of Plymouth Rock's agents. Plymouth Rock Assurance(R) and Plymouth Rock(R) are brand names and service marks used by separate underwriting, managed insurance, and management companies that offer property and casualty insurance in multiple states pursuant to licensing arrangements. Taken together, the companies write and manage $2.5 billion in auto and home insurance premiums across Connecticut, Massachusetts, New Hampshire, New Jersey, New York and Pennsylvania. Each underwriting and managed insurance company is a separate legal entity that is financially responsible only for its own insurance products. Actual coverage is subject to the language of the policy as issued. You can learn more about us by visiting plymouthrock.com.
Plymouth Rock Home Assurance has become the first US insurer to offer home insurance quotes through ChatGPT. The company launched a plugin enabling homeowners to receive real-time quotes directly within the AI platform, creating what it describes as a faster and more accessible way to shop for coverage. "We've spent a decade offering the fastest, easiest way to buy home insurance," said Bill Martin, president and CEO of Plymouth Rock Home Assurance. "Today, customers can get answers instantly through ChatGPT." The plugin is available to homeowners across all states where Plymouth Rock operates, including Massachusetts, New Jersey, Pennsylvania, Connecticut, New York and New Hampshire. The Plymouth Rock group of companies writes and manages $2.5 billion in auto and home insurance premiums across these states.
Plymouth Rock names three executives. The appointments strengthen leadership across enterprise data, claims and customer service for the Northeast personal lines insurer. Anthony R. O'Donnell // July 13, 2026 (Image credit: IIR/Gemini.) Plymouth Rock Assurance (Boston) has appointed Gavin McPhail VP and Chief Data Officer; Cornelius Young VP and Chief Claims Officer, Independent Agency Group; and Lindsay Mustard VP, Customer Service, Independent Agency Group. The appointments are intended to support Plymouth Rock's work in innovation, operational excellence and customer experience, according to a company statement. "These appointments reflect Plymouth Rock's ongoing investment in the leadership needed to drive our business forward," comments Andrew McElwee, President and COO, The Plymouth Rock Company. "Gavin, Cornelius, and Lindsay each bring deep industry experience and proven track records of leading transformation, improving customer outcomes, and delivering business results. Their leadership will help us continue to enhance the value we provide to our customers, agents, and partners." McPhail to Lead Enterprise Data Strategy As VP and Chief Data Officer, McPhail will lead Plymouth Rock's enterprise data strategy, including use of data, analytics, automation and AI to support profitable growth, operational excellence and customer experience. McPhail brings more than 20 years of leadership experience. He previously served as Executive VP and General Manager of Risk Intelligence at Fusable, where he led the company's insurance risk intelligence data-as-a-service business. Plymouth Rock says his experience includes enterprise-scale growth initiatives, data and analytics modernization, acquisition integration and operational transformation for Fortune 100 organizations. Young to Lead Independent Agency Claims As VP and Chief Claims Officer, Independent Agency Group, Young will lead the group's claims organization, with responsibility for operational excellence, claims customer experience and adoption of data, analytics and AI across the claims lifecycle. Young previously served as Chief Insurance Officer at Cambridge Mobile Telematics, where he led insurance strategy and helped develop AI-powered telematics, crash detection, digital claims workflow and risk-insight capabilities. Before that, he spent more than 13 years at Liberty Mutual Insurance in leadership roles across claims, strategy and analytics. Mustard to Lead Customer Service As VP, Customer Service, Independent Agency Group, Mustard will lead customer service operations across service center operations, underwriting, agency and sales operations, compliance, project management and customer experience. Mustard most recently held senior leadership roles at Jenius Bank, including Head of Strategy and Head of Product Engagement. She previously held Senior VP roles at Citizens Bank and earlier worked as a Project Leader at Boston Consulting Group. Plymouth Rock provides auto and home insurance across Connecticut, Massachusetts, New Hampshire, New Jersey, New York and Pennsylvania. The company says its underwriting, managed insurance and management companies write and manage $2.5 billion in auto and home insurance premium.
Plymouth Rock Assurance strengthens leadership team with strategic appointments. BOSTON - July 13, 2026 - Plymouth Rock Assurance, a leading auto and home insurance provider in the Northeast, announced the appointments of three experienced insurance and financial services leaders to key executive roles, reinforcing Plymouth Rock's commitment to innovation, operational excellence, and exceptional customer experiences. Plymouth Rock has recently appointed Gavin McPhail as Vice President and Chief Data Officer; Cornelius Young as Vice President and Chief Claims Officer, Independent Agency Group; and Lindsay Mustard as Vice President, Customer Service, Independent Agency Group. "These appointments reflect Plymouth Rock's ongoing investment in the leadership needed to drive our business forward," said Andrew McElwee, President and Chief Operating Officer at The Plymouth Rock Company. "Gavin, Cornelius, and Lindsay each bring deep industry experience and proven track records of leading transformation, improving customer outcomes, and delivering business results. Their leadership will help us continue to enhance the value we provide to our customers, agents, and partners." Gavin McPhail Named Vice President and Chief Data Officer As Vice President and Chief Data Officer, McPhail will lead Plymouth Rock's enterprise data strategy, advancing Plymouth Rock's use of data, analytics, automation, and artificial intelligence (AI) to drive profitable growth, operational excellence, and exceptional customer experiences. He will partner with business and technology leaders to strengthen data as a strategic asset, accelerating innovation and delivering measurable value across underwriting, claims, risk management, and customer operations. McPhail is an accomplished executive with more than 20 years of leadership experience. He has a proven track record of leading enterprise-scale growth initiatives, modernizing data and analytics capabilities, integrating acquisitions, and delivering operational transformation for Fortune 100 organizations. Prior to joining Plymouth Rock, McPhail served as Executive Vice President and General Manager of Risk Intelligence at Fusable, where he led the company's insurance risk intelligence data-as-a-service business. He earned an MBA from the Haas School of Business at the University of California, Berkeley; a Master of Science in Information & Telecommunication Systems from The Johns Hopkins University; and a Bachelor of Science in Finance from the University of Maryland, College Park. Cornelius Young Named Vice President and Chief Claims Officer, Independent Agency Group As Chief Claims Officer, Young will lead the Independent Agency Group's claims organization, with responsibility for driving operational excellence, enhancing the claims customer experience, and accelerating the adoption of data, analytics, and AI across the claims lifecycle. Young brings more than two decades of insurance leadership experience spanning claims operations, analytics, product innovation, and technology transformation. Throughout his career, he has led initiatives focused on improving claim outcomes, creating exceptional customer experiences and leveraging data to drive results. Prior to joining Plymouth Rock, he served as the Chief Insurance Officer at Cambridge Mobile Telematics, where he led insurance strategy and developed AI-powered solutions that transformed how insurers leverage telematics, crash detection, digital claims workflows, and risk insights. Prior to Cambridge Mobile Telematics, Young spent more than 13 years at Liberty Mutual Insurance, where he held a variety of leadership positions across claims, strategy and analytics. During his tenure, he led claims transformation initiatives, including efforts focused on fraud detection, predictive analytics, operational efficiency, and policyholder experience improvements. Young holds an MBA from the Boston College Carroll School of Management and a Bachelor of Science in Business Administration from Northeastern University. Lindsay Mustard Named Vice President, Customer Service, Independent Agency Group As Vice President, Customer Service, Mustard will lead the Independent Agency Group's Customer Service organization, with responsibility spanning all customer service operations including Service Center Operations, Underwriting, Agency and Sales Operations, Compliance, Project Management, and Customer Experience. She will focus on elevating service delivery, driving operational efficiency, and advancing customer-centric initiatives across the organization. Mustard brings deep experience working at the intersection of customer experience, digital innovation, and operational excellence. Most recently, she held senior leadership roles at Jenius Bank, including Head of Strategy and Head of Product Engagement. Prior to Jenius, she held Senior Vice President roles at Citizens Bank, and earlier in her career was a Project Leader at The Boston Consulting Group. Mustard holds an MBA from the Tuck School of Business at Dartmouth College and a Bachelor of Science in Mathematics from Trinity College. About Plymouth Rock Plymouth Rock was established to offer its customers a higher level of service and a more innovative set of products and features than they would expect from an insurance company. Plymouth Rock's innovative approach puts customers' convenience and satisfaction first, giving them the choice to do business the way they want - online, using a mobile device, by phone or with one of Plymouth Rock's agents. Plymouth Rock Assurance(R) and Plymouth Rock(R) are brand names and service marks used by separate underwriting, managed insurance, and management companies that offer property and casualty insurance in multiple states pursuant to licensing arrangements. Taken together, the companies write and manage $2.5 billion in auto and home insurance premiums across Connecticut, Massachusetts, New Hampshire, New Jersey, New York and Pennsylvania. Each underwriting and managed insurance company is a separate legal entity that is financially responsible only for its own insurance products. Actual coverage is subject to the language of the policy as issued. You can learn more about Plymouth Rock Company by visiting plymouthrock.com.