Senior Leadership Team and Management

Senior Leadership Team and Management

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.
James Stone
headshot of Andrew McElwee President and Chief Operating Officer
James Stone

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.”
headshot of Andrew McElwee President and Chief Operating Officer


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.

Mary Boyd

President and CEO, Plymouth Rock Assurance Independent Agency Group
Mary joined Plymouth Rock in 2018 and leads our Independent Agency business, including Independent Agency Auto, Pilgrim Services and Umbrella Liability. Mary has served in senior executive roles over a 25+ year career, with 15 years in High Net Worth personal insurance at Chubb/ACE. She joined Plymouth Rock from The Hartford, where she managed their AARP partnership along with responsibility for their personal lines agency and direct channels. Mary has dual degrees in Applied Mathematics and Economics from Rutgers University. Outside of work, Mary is a youth sports coach and mentors businesspersons and entrepreneurs.

Bill Martin

President and CEO, Plymouth Rock Home Assurance
Bill joined Plymouth Rock in 2016 and is in charge of our property insurance business and reinsurance programs. Bill has over 30 years of experience in the insurance industry. Bill was formerly President of Bankers Insurance, winning a Celent Model Insurer award in 2014 for simplifying homeowners insurance shopping. He also founded a startup with a new approach to flood insurance and has held senior positions at Farmers Insurance, Progressive and Travelers. Bill is a graduate of Stanford University, with a degree in Survey Data Research. He is a frequent speaker and author on insurance issues and has served on the Institute for Business and Home Safety and other safety organizations. He is an active board member of nonprofits that combat poverty and aid those with intellectual and developmental disabilities. He is an avid sailor, skier and trombone player.

Jeff Briglia

President and CEO, Plymouth Rock Management Company of New Jersey
Jeff joined Plymouth Rock in 2020 and oversees our direct-to-customer and exclusive agent auto businesses. He is an experienced veteran of more than two decades in the insurance industry, with a focus on improving the customer experience. Prior to joining Plymouth Rock, Jeff was Metromile Insurance’s first ever Chief Insurance Officer and Chief Operating Officer, in charge of operations (including an automated customer claim process). He has also served in key leadership roles at Progressive and Allstate. Jeff has a civil engineering degree from the University at Buffalo and a MBA from Carnegie Mellon University. Outside of the office, Jeff has been a drummer in local cover bands, volunteers in the community and enjoys biking, hiking and other activities with his family and rescue dog.

Board of Directors

The Plymouth Rock Company Incorporated
James M. Stone, Chairman

James N. Bailey

Hal Belodoff

Michael J. Johnston

Wilmot H. Kidd, III

Andrew McElwee

Norman L. Rosenthal

Sandra A. Urie

Sir Peter J. Wood