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Current Job Openings at Sylvia Group



Employee Benefits Account Manager

The next step in your career

If you’re an achievement-oriented, experienced benefits professional who thrives on both working independently and collaborating with other dedicated colleagues to meet clients’ needs, we have an opportunity for you to join one of the region’s most respected agencies. The Employee Benefits Division Account Manager will provide industry expertise to deliver innovative solutions while growing accounts and building on our reputation for prompt, friendly customer service. 

What you’ll be doing

Under the direction of the Employee Benefits Division Manager, the Account Manager will assist Account Executives in administering an effective program that will retain current major accounts and attract additional accounts for the continued profitable growth of the agency.

In your tool kit

Qualified candidates must possess excellent technical knowledge of employee benefits concepts as well as a demonstrated proficiency in working with different product types and dissecting proposals to identify the nuances within them. Excellent oral and written communications skills are essential, as is the ability to use Excel to prepare exhibits and proposals that illustrate multiple scenarios and complex concepts. Life, Accident and Health licensure are required; a bachelor’s degree is preferred..

High expectations

The Account Manager will dependably meet deadlines, handle multiple tasks simultaneously and adapt to changing circumstances, occasionally in high-pressure situations. Doing the job successfully requires an ability to work with different personality styles while demonstrating empathy for clients’, carriers’ and co-workers’ situations.




Build on your success

To continue our growth and expand our services, Sylvia Group is seeking competitive, results-driven professionals for Massachusetts insurance jobs and Massachusetts benefits jobs in the Boston area and SouthCoast region. The Producers we seek are thought leaders who understand what’s most important to clients: the business and personal risks, as well as the financial challenges, that impact their future. Ideal candidates have proven success in sales and are looking to further that success while working with a great support team and in-house resources.

What you’ll be doing

Commercial Lines Producers forge new client relationships by designing programs that reduce the cost of risk and make clients more attractive to the insurance marketplace. By analyzing level of exposure and addressing gaps in coverage with your clients, you’ll serve as a trusted partner in developing solutions that drive down their long-term costs and help them meet their business objectives.

Personal Insurance Producers generate business by recognizing and addressing current and prospective clients’ needs and working together to find solutions that are right for them. Under the direction of the Sales Manager, you’ll be able to exercise your drive to work independently while enjoying the support of an outstanding team.

Employee Benefits Producers drive new revenue by identifying, qualifying, developing and closing new opportunities with clients from small to midsize companies. You’ll cultivate relationships with sources of new business and meet with prospects to identify their needs, explain our insurance products and implement a sales strategy. You’ll also expand sales in existing accounts by introducing new products  and services.

In your tool kit

An existing book of business, a strong commitment to industry education, advanced communication skills, networking and relationship building are essential to getting the job done. Qualified candidates must have a minimum of a bachelor’s degree, and demonstrate strong self-management skills and leadership qualities. For Benefits candidates, experience analyzing group health, dental, life and disability quotes and presenting benefit-plan options is preferred but not essential.

High expectations

As a Producer, you'll pursue and close sales of new and existing accounts while retaining an assigned book of business. You'll be required to write new business that meets or exceeds targets for premium volume, commission and number of accounts while adhering to agency service standards and timelines. Producers plan, lead and control their personal production levels and servicing in a manner consistent with agency goals for growth, mix of business and profitability. 



  • “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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