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Sylvia Group

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The next step in your career

If you’re an achievement-oriented professional who thrives on both working independently and collaborating with other dedicated colleagues to meet clients’ needs, you’ll fit right in at Sylvia Group, one of the region’s most respected agencies. We work hard because we believe in our promise – “Many solutions, one trusted team” — and love what we do.


A great place to live and work

Based in Dartmouth on Massachusetts’ beautiful SouthCoast, Sylvia Group is the first six-time winner of the Massachusetts Association of Insurance Agents’ Five Star Designation for all-around industry excellence. We work with businesses and individuals, offering products and services to meet our clients’ needs in the areas of insurance, employee benefits and financial planning.

We’re a family-owned, community-focused business with more than 60 years of experience in meeting the needs of our clients while providing state-of-the art training and generous wages, benefits and time off to our employees. And we have fun. From our Friday company breakfasts and seasonal outings to our volunteer work at local nonprofits and the region’s many festivals, our team has a good time working together and supporting our dynamic, diverse community.


What you’ll be doing

As a member of the Sylvia Group team, you’ll exercise your strengths and enhance your expertise while also having the opportunity to work across disciplines with colleagues in other departments. You’ll enjoy strong internal support and engage in ongoing professional development through external training and educational programs.


In your tool kit

Personalized service was a founding imperative of our agency more than six decades ago, and it remains vital to our success today, so strong communications skills are a must. We expect our candidates to have a solid foundation for the position to which they aspire, including a strong understanding of industry principles, basic or better technical skills and an unwavering belief in professional ethics.


High expectations

Not many agencies receive the MAIA’s Five Star Designation, and there’s a reason for that: Earning it is hard. But we’ve earned renewal of the designation every year in which we’ve been because our team wouldn’t have it any other way. If you join our team, you can expect to be among the best in the business.


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Testimonials

  • “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

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