Who We Are

The Sylvia Group

Professionals with a stake in your success.

One Stop ResourceAs an independent agency operating on Massachusetts’ SouthCoast for more than 60 years, Sylvia Group is the trusted one-stop resource clients call on first for objective advice and innovative solutions. With a can-do attitude, high standards and genuine care for the people we serve, we’re relentless in pursuing solutions for each client and helping you understand all the details. The result? You can feel confident in your insurance, employee benefits and financial planning decisions.

The resources you need to protect your world

Our team of experts works with clients to integrate services, helping you manage the various facets of your life, your business and your future under one roof, with people you trust. We work with you to identify concerns, offer objective advice and come up with solutions that fit your needs.

Discover the power of knowledge, and of community.

We’ve grown by hiring bright, hard-working people who share our values of serving our clients and our community. With low turnover – many of our employees have been here more than 20 years – and a commitment to industry education, we offer our collective expertise in an array of related areas. And with a deep commitment to the cities, towns, civic organizations and institutions around us, we offer a network of dependable resources throughout the area to help you with other challenges you may face.

A long history of forward thinking.

We’re a third-generation, locally owned agency, proud to carry on our family tradition. Our founder, Louis G. Sylvia, launched the agency in 1950 after working for a national insurance company. He felt he could offer better customer service on his own – and he did. He started with personal lines, working out of his home in New Bedford. His son Vincent P. Sylvia Sr. joined the company in 1960 and became President in 1970. The third generation began when Vincent Sylvia’s daughter Maureen Sylvia Armstrong came on board as Agency Manager in 1986. In 1998, her sister Beth Sylvia Caldwell joined the agency, and in 2003 the sisters purchased the company.

Over the years, the agency grew and moved to larger headquarters. Today, we’re one of the largest agencies in Southeastern Massachusetts, certified as a Woman Owned Business Enterprise with the Massachusetts Supplier Diversity Office (SDO). We’re proud to be one of only a few agencies to receive the prestigious Five Star Agency designation from the Massachusetts Association of Insurance Agents (MAIA), reflecting our continuous commitment to providing superior knowledge, service and value to each client.

Today Sylvia Group is licensed in:

  • California
  • Connecticut
  • Deleware
  • District of Columbia
  • Florida
  • Georgia
  • Maine
  • Massachusetts
  • Michigan
  • New Hampshire
  • New Jersey
  • New York
  • North Carolina
  • Ohio
  • Pennsylvania
  • Rhode Island
  • South Carolina
  • Vermont


  • “When I needed assistance with my business insurance program, Jill White immediately responded – and, even more important, she listened. She understood the challenges I had with my former agent, and she and the Sylvia Group team designed a program specific to my restaurant’s needs. I’m confident that with Jill’s expertise and personal attention, Fay’s is in good hands. That gives me the peace of mind to focus on what my family and I do best: serve delicious food and provide great customer service while running a successful business.”

    – Evelyn Bettencourt, Owner, Fay's Restaurant and Knotty Pine Fine New England Catering

  • “Thanks to John Beauregard and the professionals at Sylvia Group, our MassMEDIC membership has paid immediate dividends. Through the BIO Business Solutions® program, Primo Medical received a significant premium reduction on our Professional Liability policy. In addition, utilizing Chubb as our insurance provider and Sylvia Group as our broker, we’re confident that we have business partners who truly understand our insurance needs, provide outstanding loss control services and continue to work with us to lower our total cost of risk.”

    – Christopher LaPlante, Chief Financial Officer, Primo Medical Group

  • “I love your staff. Since we moved over to Sylvia Group for our insurance what is it, maybe three or four weeks? I have had more communication and attention from them than I had for the what, seven or eight years? with my former agency! You have a great team.”

    – Pat Cassan, Ocean Explorium

  • “You have to have somebody like Judy Besse working with you. She’s very detail-oriented and patient. I’d be lost in a quagmire of laws, rules, regulations… I want somebody on my team as I have with Judy.”

    - Paula Gendreau, Business Manager, Greater New Bedford Regional Voc-Tech High School

  • “I want to thank you for this incredible resource (ThinkHR). We will be accessing it frequently and appreciate Sylvia Group making this available to Advanced Eye Centers.”

    Paul C. Abrantes, Executive Director, Advanced Eye Centers

  • “I so appreciate Julie Jennings' help with Medicare planning. It is a relief to be able to consult with a knowledgeable professional on insurance issues. I have no idea how people do this without such help.”

    – Chris Black, Personal Insurance client

  • "Working with Judy Besse can be pretty interesting because she sets the bar so high. And because she’s putting the customer first, she’s willing to put choices on the table that a lot of brokers just aren’t going to consider because they don’t want to take the haircut."

    – Ed Belt, CEO, Primarily Care, Inc.

  • “Working with Sylvia Group over recent years has taken our insurance issues from 'groans and moans' to 'no problem.' Rose Lopes, our Account Manager, is one of the most responsive people I have ever worked with. She responds immediately to questions or special requests. It is such a pleasure to work with Rose, who does whatever it takes to find a solution to our needs. We are very pleased… She always has our interests in mind.”

    – Lynne Foley, Director of Human Resources, Five Star Companies, Inc.

  • “Judy Besse and Sylvia Group do a wonderful job. Judy’s skills, knowledge of the (benefits) industry and manner of presenting complicated things in an easy-to-understand fashion are unparalleled.”

    - Tom Riley, M.P.A., Executive Director, Better Community Living

  • “We wanted to enhance our employee benefits offering, but we didn’t have the time or expertise to explore the myriad of options. Judy Besse consulted with us and provided detailed information that made a complex choice easy, enabling us to maximize our ROI. And she managed the entire process right through to implementation – including employee communication, enrollment and carrier accountability.”

    – Tom Donaruma, Director of HR, Brahmin Leather Works

  • "Sylvia Group is by far the best insurance agency I have ever dealt with, both personally and in my business. They provide customer support that is not found in other agencies. For example, they take a personal interest in their clients, calls are always taken or returned immediately, and during reviews suggestions are made to offer the most cost effective and comprehensive coverage. When claims occur, they have always been there to facilitate the process. It has truly been a pleasure to have them represent me in my insurance needs."

    - William N. Whelan, Chairman, Whelan Associates LLC

ACA Certified