Career Opportunities

Find your next career opportunity with Chesapeake Employers’ Insurance Company.


Make a Difference

People. It's all about people. Family. Neighbors. Friends. Peers. Keeping people safe at work is our top priority.

When you're a part of the Chesapeake Employers family, your contributions will impact the lives of working people all across Maryland. We believe in treating people with the respect, care, and dignity they deserve. If you would like to work for an organization that strives to do the best for its customers, employees, and communities, consider joining Chesapeake Employers and growing your career with Maryland's largest writer of workers' compensation insurance.

Proudly Serving Maryland

Chesapeake Employers has been providing workers' compensation insurance to Maryland businesses since 1914.


If you want to grow your skills and be a part of a caring organization that promotes work-life balance and is meeting the challenges of an evolving industry, then Chesapeake Employers is the place for you.

Health & Disability Benefits

  • Health, dental, vision, and life insurance
  • FMLA
  • Short term/Long term disability
  • Health savings account
  • AD&D

Financial Benefits

  • Competitive compensation & bonus program
  • 401k plan
  • Paid vacation and sick leave
  • Paid holidays
Wellbeing benefits description

Wellbeing Benefits

  • Flexible work schedule
  • Health & Wellness Program
  • Employee Assistance Program
Perks description

Bonus Perks

  • Employee Volunteer Program (paid 12 hours/annually)
  • Free tickets to community attractions
  • Employee appreciation events
  • Free parking

Chesapeake Employers’ Insurance Company is an Equal Opportunity Employer. All job offers are contingent upon the successful completion of a background check and drug screening.