Gary F. Terry


Executive Vice President and Managing Director

For more than 35 years, Gary has been providing clients with his expertise associated with executive supplemental benefit plans. Gary is the co-founder of The Westport Group (TWG), which specializes in the design and implementation of supplemental disability and life insurance programs.

His current focus is designing multi-life programs to cover the unique needs of the highly compensated executives, partners and employees of TWG’s clients. These programs are structured to provide flexible, cost-effective, voluntary and company-paid solutions for life and disability insurance. He is also one of the architects of our proprietary high-limit long-term disability plan created to resolve the specific life and disability needs of these groups of highly compensated individuals.

Gary has authored numerous articles on these subjects, which have appeared in national publications including Human Resource Executive, Inside Business, Benefits Selling, Life Insurance Selling, Risk Insurance On-Line,, along with several CPA magazines and business journals across the country.

Gary is a former Executive Vice President and Managing Director of Westport Worldwide/HRH, a firm that specialized in the design, implementation and funding of Deferred Compensation Plans (DCP’s), Supplement Executive Retirement Programs (SERP’s) and the use of Corporate Owned Life Insurance (COLI). In addition, he was the founder of the Executive Benefits Group, a division of Compensation Resources Group (CRG), which was purchased by the Hobbs Group in 2000.

Gary currently resides in Hingham, Massachusetts with his wife Carolyn. He has three adult children, Nicole, Christina and Melissa. Gary is an avid skier and enjoys ski trips to his home in Vail, Colorado. A licensed contractor, Gary and his spouse enjoy designing and building high end homes. He has a passion for real estate and real estate development.

Gary is a graduate of the Northeastern School of Business, with honors, as well as an alumnus of Norwich University where he served as a member of The Norwich Board of Trustees.