Senior leadership team and management

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Above all, Plymouth Rock's senior leadership team is committed to the welfare of our customers and employees. They are passionate about building our company and our talent. Meet the people who set the strategy that guides our business to deliver superior service and innovative results.

Jim Stone

Chairman and CEO

Jim Stone founded Plymouth Rock in 1982, and has been its CEO ever since. He holds a Ph.D. in economics from Harvard University, where he taught for several years in the 1970’s. He was then named Massachusetts Commissioner of Insurance, and in 1979 was named chairman of the United States Commodity Futures Trading Commission. Jim now serves as a director of Cold Spring Harbor Laboratory, a genetics institute, and of ProPublica, a journalism nonprofit specializing in investigative reporting. He chairs the School on the Move Prize panel for the benefit of the Boston public school system, and he is a fellow of the American Academy of Arts and Sciences. He is also chairman emeritus of Management Sciences for Health, an international public health nonprofit. He is the author of numerous articles and “Five Easy Theses: Commonsense Solutions to America’s Greatest Economic Challenges.”

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ANDREW McELWEE

President and Chief Operating Officer

Andy McElwee joined Plymouth Rock in 2022 from American Family Insurance, where he was the Enterprise Chief Underwriting Officer. Prior to American Family, Andy was President and Chief Operating Officer of Homesite, having joined the company in 2011. Prior to Homesite, Andy spent 25 years with affiliates of The Chubb Corporation in senior positions including Executive Vice President of Chubb & Son and Chief Operating Officer of Chubb Personal Insurance and Chubb Accident and Health. Andy has a B.A. from Davidson College and a J.D. from the University of Virginia School of Law. He has served on the boards of Davidson College, the American Folk Art Museum, and the International Tennis Hall of Fame. He has also served as the president of the Davidson College Alumni Association and as a member of the Alumni Council of the University of Virginia School of Law.

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Greg Kalinsky

President and CEO of Plymouth Rock Management Company of New Jersey

As President and CEO, Greg Kalinsky oversees Plymouth Rock’s direct-to-consumer and exclusive agent auto insurance division, based out of its Woodbridge, N.J. office. Prior to joining Plymouth Rock, Kalinsky had a remarkable 37-year career at GEICO, holding multiple leadership roles across the company. His responsibilities spanned Underwriting and Product Management, Actuarial Pricing and Reserving, Sales and Service, and Real Estate and Facilities Management. He was elected to the GEICO Board of Directors and served as Executive Vice President, overseeing all operations, including $40 billion in written premium and 35,000 employees across 15 offices nationwide. Kalinsky’s leadership extended to every aspect of GEICO’s direct-to-consumer business. He holds a B.A. and J.D. from George Mason University.

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Bill Martin

President and CEO of Plymouth Rock Home Assurance

Bill currently oversees Plymouth Rock’s property insurance business and reinsurance programs. Since joining the company in 2016, he has spearheaded multiple game-changing innovations, including an award-winning “quick quote” process that delivers home and rental insurance quotes to customers in seconds. The result has been a tenfold increase in new policy quotes and 65% sales growth since its launch.

Prior to Plymouth Rock, Bill was President of Bankers Insurance and held senior positions at Farmers Insurance, Progressive and Travelers. He also founded several startup companies, including Neptune Flood. All told, Bill has 40 years of experience in the insurance industry.

A renowned insurance author and speaker, Bill has served on the boards of the Insurance Institute for Highway Safety and Institute for Business and Home Safety. Today he is an active board member of nonprofits that combat poverty and aid those with intellectual and developmental disabilities. In his spare time, Bill enjoys sailing, skiing and playing the trombone.

Bill is a graduate of Stanford University.

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Chris Taylor

President and Chief Executive Officer, Plymouth Rock Assurance Corporation

Chris Taylor is President and CEO of Plymouth Rock’s Independent Agency Group, which manages more than $1.4 billion of personal auto, commercial auto, motorcycle and umbrella liability premium.

Taylor joined Plymouth Rock in October 2026 and brings more than a decade of personal lines leadership and deep experience in the independent agency channel. Most recently, Chris served 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. There, he built and strengthened independent agency relationships, expanded the company’s portfolio, and led profitable countrywide growth.

Chris previously worked at Plymouth Rock, where he helped lead the company’s entry into the New York and Pennsylvania auto insurance markets. He began his insurance career in Product Management at The Hartford.

Chris holds a BS in Chemistry and an MBA from the University of Connecticut, and an MS in Chemistry from the University of Illinois.

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Senior leadership team and management