Insurance industry veteran and former GEICO executive will lead the company’s Direct Auto Group
Plymouth Rock Assurance has named Greg Kalinsky as President and Chief Executive Officer of the Plymouth Rock Management Company of New Jersey, effective February 24, 2025. In this role, Kalinsky will oversee Plymouth Rock’s direct-to-consumer and exclusive agent auto insurance division, based out of its Woodbridge, N.J. office. He will report to Andrew McElwee, President and Chief Operating Officer of The Plymouth Rock Company.
“We are thrilled to welcome Greg to Plymouth Rock to lead our direct-to-consumer auto division,” said Jim Stone, Founder, Chairman, and Chief Executive Officer of The Plymouth Rock Company. “Greg is a distinguished leader with a deep understanding of the insurance industry and experience across nearly every function of the business. We look forward to Greg’s contributions as Plymouth Rock continues its growth journey.”
Kalinsky brings an extraordinary depth of experience to Plymouth Rock, with a remarkable 37-year career at GEICO. Starting in the mailroom while attending college at night, he steadily rose through the ranks, 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, cementing his reputation as a seasoned industry leader.
“I am honored to join the Plymouth Rock team and excited about the opportunity to continue to grow our business,” said Kalinsky “I have a deep appreciation for the direct-to-consumer business model and I look forward to working with the team to deliver exceptional value to customers and build on Plymouth Rock’s strong foundation.”
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, with a mobile app, by phone or by contacting their Plymouth Rock agent. Customers can chat, text or email to get answers quickly and easily.
Plymouth Rock Assurance® and Plymouth Rock® are brand names and service marks used by separate underwriting, managed insurance and management companies that offer property and casualty insurance in multiple states. Taken together, the companies write and manage more than $2.3 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. You can learn more about us by visiting plymouthrock.com.
