Family Values, Professional Excellence
TMS Insurance Group has been protecting families and businesses across Massachusetts and the East Coast with personalized service and unwavering commitment to our clients.
Built on Family Foundation
TMS Insurance Group was founded with a simple belief: insurance should be personal. As a family-owned business, we understand that behind every policy is a family, a dream, and a future that deserves protection.
Our founders started this company with the vision of providing comprehensive insurance solutions while maintaining the personal touch that only a family business can offer. Today, we continue that tradition with the same values that guided us from day one.
Family
Owned & Operated
15+
Insurance Carriers
East Coast
Coverage Area
24/7
Claims Support
Meet the TMS Insurance Group Team
Brothers Tommy and Michael Pratt bring together years of insurance experience and a shared commitment to personalized service.
Thomas (Tommy) Pratt
Co-Founder & Partner
Thomas (Tommy) Pratt was born and raised on Cape Cod and graduated from High Point University in 2014. He began his insurance career at New York Life, where he gained valuable experience helping clients protect their financial futures and what matters most to them.
After several years, Thomas returned to his family's business, gaining a broader perspective on business operations and sustainable growth strategies. In 2024, he partnered with his brother, Michael Pratt, to launch their own branch under Oxford Millin Insurance—forming TMS Insurance Group. Together, they've built a firm focused on personal relationships, long-term trust, and customized coverage tailored to each client's unique needs.
Outside the office, Thomas enjoys spending time on the golf course or boating—activities that help him recharge and stay grounded. He currently lives north of Boston with his wife, Heather.
Michael Pratt
Co-Founder & Partner
Born and raised on Cape Cod, Michael Pratt earned his degree in Finance from Roger Williams University before launching his insurance career in 2017 with Oxford Millin Insurance Agency. There, he gained hands-on experience in both personal and commercial lines.
To broaden his industry perspective, Michael went on to serve as an account manager at an insurtech company where he spent two years immersed in the dynamic, digital side of insurance.
Motivated by a strong passion for relationship-building and client-focused service, Michael returned to his roots in traditional insurance. Partnering with his brother Tommy, the two rejoined Oxford Millin Insurance to launch TMS Insurance Group—an agency committed to delivering responsive, personalized coverage solutions to clients across Massachusetts and beyond.
Outside of work, Michael enjoys boating, golfing, and spending quality time with friends and family whenever he can.
What Drives Us Every Day
Our core values shape every interaction, every policy recommendation, and every relationship we build.
Family First
We treat every client like family because we understand that insurance is about protecting the people and things you love most.
Trust & Integrity
Honest advice, transparent processes, and ethical practices form the foundation of every relationship we build.
Excellence
We strive for excellence in everything we do, from policy selection to claims support and customer service.
Why Choose TMS Insurance Group
Experience the difference that comes from working with a family-owned agency that truly cares about your protection.
Personal Relationships
You'll work with the same dedicated agent who gets to know you and your unique needs.
Comprehensive Coverage
Access to multiple carriers means we can find the right coverage at the right price for your situation.
Always Available
When you need us most, we're here. Our commitment to service doesn't end when you sign the policy.
Broad Coverage Area
Deep understanding of East Coast risks and regulations ensures you get coverage that truly protects.
Tailored Solutions
No cookie-cutter policies. Every recommendation is customized to fit your specific needs and budget.
Claims Advocacy
We advocate for you during claims, ensuring you get the fair settlement you deserve.
Ready to Experience the TMS Difference?
Join those who trust TMS Insurance Group to protect what matters most to them.