Join Our Team

Your role is straightforward: provide outstanding support for our clients' insurance needs while advancing your own career and skills.

Are you passionate about learning, growth, and being the best in your field? At Sterling Insurance Group, we celebrate diverse talents, perspectives, and innovative ideas. We're looking for individuals who are driven to deliver exceptional service, continuously improve, and make a lasting impact in the industry.

  • Renewals Processor - Trainee

    No experience required. This is a support role that focuses on renewals and other processing functions. Candidate will be required to obtain a MA Property & Casualty License. Learn from the best and start a career in the unique insurance industry on the Vineyard.

    Primary Location: Vineyard Haven, Martha’s Vineyard, MA

    Schedule: Full-time 40 hours per week

    Pay: $65k. Pay is commensurate with experience.

    Apply Now

  • Personal Lines Insurance Agent

    Requires 3+ years of experience with active MA P&C License and advance insurance designations. This role focuses on insurance renewals and sales of personal lines, a focus on high value homes with coastal risk and advanced knowledge of excess & surplus lines.


    Primary Location:     Boston & Vineyard Haven, Martha’s Vineyard, MA

    Schedule: Full-time, 40 hour per week

    Pay: $68k+. Pay is commensurate with experience.

    Apply Now

  • Commercial Lines Insurance Agent

    Requires 5+ years of experience with active MA P&C License and advance insurance designations. This role focuses on insurance renewals and sales of commercial lines, a focus on restaurants and commercial property. An advanced knowledge of excess & surplus lines.


    Primary Location:     Boston and/or Vineyard Haven, Martha’s Vineyard, MA
    Schedule:     Full-time, 40 hours per week

    Pay: $72k+. Pay is commensurate with experience.

    Apply Now

  • Director of Operations

    We are seeking an entry-level Director of Operations with a strong background in Commercial and Personal Lines Customer Service Representative (CSR) roles. With over 10 years of experience in the insurance industry, the ideal candidate has developed exceptional skills in managing client relations, streamlining operations, and ensuring compliance with industry standards. This role requires a proactive leader who can enhance productivity through effective workflow strategies and foster a collaborative team environment. Experience with bilingual Agency workflows or ability to speak Mandarin or Cantonese is a plus. If you’re ready to take the next step in your career and bring your expertise to a dynamic organization, we want to hear from you!

    Primary Location:     On-Site, Boston, MA

    Schedule:     Full-time, 40-60 hours per week

    Apply Now

What we look for:

We’re looking for talented individuals who strive for excellence and have a passion for helping others and solving problems. Education is a primary pillar at Sterling Insurance Group and we strongly encourage a MA Property and Casualty license, which is one of the elements for a successful insurance career.

Critical personality traits for success at Sterling Insurance Group include:

  • Ability to multi-task, problem solve, follow-up and adhere to deadlines

  • Strong oral and written communication skills

  • Prompt, Attentive and Professional conduct and manner

  • Exhibits a love of learning and technology

Equal Opportunity Employer.

Duties and Responsibilities:

  • Provide exceptional service, consultation and insurance education to clientele

  • Demonstrate and articulate thorough understanding of insurance products, services and coverage

  • Provide consultative approach to identify and respond to client needs

  • Underwrite and evaluate risks to ensure proper coverage is placed

  • Review monthly renewal list and be sure policies are renewed and bound by expiration date

  • Act with honesty, integrity, and in compliance with Agency’s fiduciary responsibility

  • Strong attention to detail and conscientious, thorough approach to work

  • Act in compliance with all agency required workflows, policies, procedures including all required documentation

  • Understand and fully utilize available technologies and equipment to maximize service and efficiency

  • Document all client and company activity in agency management system

  • Perform duties in responsive, timely manner, escalating to manager when necessary

  • Ability to understand how details relate to “big picture” concepts

  • Ability to interact professionally and courteously with employees, clients, carriers and vendors etc.

  • Assist and direct clients to appropriate resources in claim situations

  • Ability to take own initiative and be resourceful

  • Networking and community involvement encouraged

Full-Time Benefits:

  • A high-tech luxury office with every necessary tool and professional environment.

  • Every federal holiday off with pay, plus two bonus days.

  • Minimum of 3 weeks paid time off.

  • Qualifying employees participate in a Growth Incentive program.

  • 401k Retirement Plan with employer match.

  • Paid professional development including licensing and insurance education.

  • Flexible and understanding management.