Join Our Team

Do you aspire to be the best, to learn and to grow with a great company? We value different talents, perspectives and ideas. We’re searching for teammates that want to provide excellent service to our clients and be an asset to our team.

The job is simple, take care of our clients insurance needs. Our primary client is any individual owning a home on Martha’s Vineyard, including year-round residents and seasonal or secondary homeowners.

  • Full-Time - Trainee - On-Site

    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 35 hours per week; m-thur 10a-5p Fri 10a-3:30p

    Pay: $28/hr

    Apply Now

  • Full-Time - 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 personal lines, a focus on high value homes with coastal risk.


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

    Schedule: Full-time minimum 35 hours per week; m-thur 10a-5p Fri 10a-3:30p

    Pay: $36+/hr, plus significant bonus tied to performance. Pay is commensurate with experience.

    Apply Now

  • POSITION FILLED

    Part-Time - Remote

    No experience required. This is a support role that focuses on renewals and other processing functions.


    Primary Location:     Remote


    Schedule:     Part-Time 15-20 hours per week; Flexible scheduling TBD.

    POSITION FILLED

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 (13 paid holidays off).

  • Minimum of 3 weeks paid time off (depends on experience).

  • Qualifying employees participate in a Growth Incentive program.

  • Employer sponsored medical insurance.

  • 401k Retirement Plan with employer match.

  • Paid professional development including licensing and insurance education.

  • 35 hours per week with 10am start time daily.

  • Flexible and understanding management.