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 the Northeast. In 2022, we were named the 2nd largest insurance broker in Massachusetts by the Boston Business Journal. With over 1,100 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  

See Our Openings & Submit Your Application

With offices in Maine, New Hampshire, Massachusetts, Connecticut, and New York, your next job opportunity could be closer than you think. See a comprehensive list of our openings on Workday.

Cross Insurance Summer Internship Program

Our Summer Internship Program is a ten-week program open to students entering their Junior or Senior year of college. Based out of our Portland, Maine, office, this is a paid internship that typically includes local business tours, job shadowing, and fun projects. 

What do you love about working at Cross?