Join Our Winning Team

Careers at Cross

Come See What Makes Cross a Great Place to Work

Family Owned 
From starting at the kitchen table of Woodrow Cross, to becoming one of the largest insurance providers in New England, we’ve grown rapidly over the past 65 years. We’ve still held on to our core values of integrity, hard work, and dedication, and are still privately held. 

Giving Back
Our offices inspire a culture of community by supporting causes they stand behind. From fundraising for local food banks, to volunteering at after school programs, we’re proud of the many ways our offices find to give back. Initiatives vary from branch to branch to better serve the individual communities they are located in.  

A Bright Future
We’re growing. Since our founding, we have absorbed over 150 operations, branching throughout New England. In 2020, we were named the 5th largest insurance broker in Massachusetts by the Boston Business Journal. With over 1,000 employees, we would love to see how your talent fits in with our team.

What We Offer
We’re looking for the best talent to build our team, and offer highly competitive salaries and a comprehensive benefits package that includes: 

  • 401(k)
  • Group Life/Supplemental Life
  • Group Dental
  • Group Vision
  • Group Medical
  • Short-term/Long-term Disability
  • Medical & Dependent Care Reimbursement
  • Education Reimbursement Opportunities 
  • Professional Work Environment 
  • Paid Holidays 
  • Continuing Education  

Ready to Join Our Winning Team? 

Fill out the form below and upload your resume. We look forward to hearing from you. 












    Current Openings

    • Cloud Solutions Architect

    • Personal Lines Account Manager, Bangor, ME

    • Personal Lines Sales Executive, Bangor, ME

    • Loss Control Consultant, New Gloucester, ME

    • Receptionist / Office Assistant, Lewiston, ME

    • Commercial Lines Small Business Manager, Portland, ME

    • Commercial Lines Processor, Portland, ME

    • Personal Lines Sales Executive, Portland, ME

    • Personal Lines Sales Executive, Manchester, NH

    • Personal Lines Account Manager, Manchester, NH

    • Commercial Lines Account Manager, Manchester, NH

    • Small Business Unit- Commercial Lines Account Manager, Manchester, NH

    • Commercial Lines Account Manager, Braintree, MA

    • Client Support Assistant – Private Client Group, Braintree, MA

    • Personal Lines Account Manager, Pittsfield, MA

    • Commercial Lines Account Manager, Pittsfield, MA

    • Personal Lines Account Manager, Wellesley, MA

    • Commercial Lines Account Manager, Wellesley, MA

    • Commercial Lines Claims Advocate, Wakefield, MA

    • Commercial Lines Account Manager, Wakefield, MA

    • Personal Lines Account Manager, Marshfield, MA

    • Personal Lines Account Manager, Briarcliff Manor, NY