Gary F. Terry

Executive Vice President and Managing Director (Co-founder)

Gary has spent more than 40 years leveraging his expertise in executive supplemental benefit plans. Specializing in designing tailored firm-sponsored, high-limit disability income protection solutions to address the unique needs of corporate executives, law firm partners and highly compensated employees.

Gary has implemented hundreds of programs both domestically and internationally. These plans are structured to provide flexible, cost-effective solutions for both company-paid and voluntary disability insurance protection. As one of the architects behind TWG’s proprietary high-limit long-term disability plan created to address the specific disability needs of highly compensated employees at publicly traded corporations, Gary’s knowledge and expertise played a pivotal role in progressing TWG to its current position.

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

Gary currently resides in Hingham, Massachusetts, with his wife, Carolyn. He has three adult children, Nicole, Christina and Melissa. An avid skier, Gary enjoys ski trips to his home out west. As a licensed contractor, he and Carolyn enjoy designing and building homes. He has a strong passion for real estate and real estate development.

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

Testimonials

“The top-level employees and executives in our company were subject to considerable financial exposure. The Westport Group worked with us to create a plan that protected our workers’ salary and bonus income.

Now, our employees and executives have the best, most disability insurance coverage available on the market today.”

“With its high-level commitment to quality, passion for the insurance industry, and solicitation of client input, The Westport Group consistently delivers creative solutions to employee benefit needs. Proudly partnering with Lloyd’s of London, The Westport Group covers risk like no other life & disability insurance provider can.

When we need comprehensive, customized coverage to protect our employees’ financial risk, The Westport Group is our first and only call.”

“The Westport Group showed us a better way to buy multi-life insurance. Through a solutions-based approach, they offered more flexibility than most other programs as well as solid, real-world guarantees. Through their detailed analysis of our life insurance program, they created a custom insurance solution for both our domestic and international managing directors."