TGA Insurance Brokers




President and CEO

Thomas “Tig” Gregory III has been working with many of the country’s leading agricultural, food processing, manufacturing, biotech and transportation companies for over 30 years.  He attended the University of Hartford’s Barney School of Business, graduating with degrees in insurance and finance. Upon graduation, he was awarded the Ackerman-Saval Excellence in Insurance Award — an honor bestowed to the top graduating senior within the Insurance Major.

Tig began his career in 1981 with a large regional broker in Massachusetts, and due to his quickly developed knowledge and expertise, was recruited in 1989 to join a startup firm in the Boston area as both a producer and member of the management team.  In his new role, he quickly expanded the firm’s scope beyond life science and high tech, and the company rapidly grew.  When it was sold to a national firm in February of 1995, Tig began working on his plan to launch his brokerage firm.  In July of 1995, he and a business partner opened Thomas Gregory Associates on the North Shore of Boston.  Together he and his partner grew the firm to be one of the most respected Insurance Brokerages in the Northeast, and in 2011 sold the firm to a larger regional competitor. 

In September of 2016, Tig, along with his son Andrew, left the large regional broker and opened the doors of Thomas Gregory Associates Insurance Brokers Inc. This is where Tig continues to offer an insightful, consultative approach to insuring large and intricate businesses in the agricultural, food processing, transportation, life sciences, and private equity verticals. 

Tig has unmatched expertise in understanding some of the most complex insurance risks large businesses face today. He has in-depth knowledge and understanding of how to make insurance policies and business practices meet to create a rock-solid risk management program for clients of all walks of life. 

Tom and his wife reside in Ipswich, MA where he spends any available leisure time riding and competing on his horse, My Weekend Cosmopolitan.




Executive Vice President

Andrew Gregory began his insurance career as an intern at Thomas Gregory Associates at the age of fifteen. He assisted the agency with complex, large, and middle market property and casualty accounts while learning the workings of the insurance industry. Andrew graduated from The University of Massachusetts Amherst with a degree in Legal Studies in 2010. Upon graduation, Andrew joined Thomas Gregory Associates as an assistant account manager.

Andrew worked as an understudy to his father, Thomas “Tig” Gregory. Under Tig’s mentorship, Andrew learned risk analysis and risk management best practices which gave him the proficiency to serve as an effective and trusted advisor to his clients. Andrew was promoted to producer at Thomas Gregory Associates in 2011. Five years later, in September 2016, Andrew and Tig fulfilled their life-long dream and founded Thomas Gregory Associates (TGA) Insurance Brokers, Inc. together.

Andrew strives to deliver excellent and personalized service to his clients and consistently demonstrates the significance and value of reviewing and revealing a client’s total cost of risk. Andrew advocates for the use of hardened data and key metrics to give clients of TGA Insurance Brokers the confidence to make critical business decisions on their insurance and risk management programs.

Andrew prides himself on being one of few students of the insurance industry in his generation. With over a decade of experience, Andrew is excited to continue his insurance career alongside his father and bring insight and expertise to large, complex risks in the agricultural, food processing, manufacturing, private equity, and life sciences businesses.

Andrew loves the outdoors and is a big believer in seasonally seeking out free-ranged, organic meat and poultry with his German Shorthaired hunting companion, Otter.