Employment Opportunities

Cumberland Insurance Group employs more than 160 talented people in four states. Our hometown atmosphere allows our dedicated insurance professionals to provide the best service possible to our agents, as well as to our individual policyholders. If you think insurance is the field for you, we’d love to have you as part of our Cumberland family!


  • Competitive Salaries
  • Medical Insurance
  • Prescription Drug Plan
  • Dental
  • Disability Plans
  • Life Insurance and AD&D
  • 401(k) Savings Plan
  • Flexible Spending Account
  • Holidays, Vacation, and Sick/Personal Days
  • Flexible Work Hours Scheduling
  • Educational Assistance 
  • Employee Assistance Program

Cumberland Job Opportunities

Marketing Representative

This position is responsible for the successful development and execution of the territorial sales and business development plans for Delaware, Maryland and Pennsylvania, in alignment with current corporate strategies and products. It is a requirement that the selected candidate resides in or is willing to relocate, at their own expense, to southern central Pennsylvania or northern Maryland. It is also a requirement that the candidate has the ability to operate an automobile and possesses a valid driver’s license. For a full job description and an application, please click here.


Interested About Careers in Insurance?
Click here to learn more about careers in the insurance industry.

Working at Cumberland

Cumberland employees who are interested in pursuing career development opportunities are encouraged to apply for open positions through our internal job posting program. Cumberland works in partnership with Cumberland County College (NJ) to offer Certificate and Associates Degree programs in Business Management/Insurance. Many of our employees have earned industry-respected designations through the Insurance Institute of America.


Cumberland's Employment Policies

The management of Cumberland firmly believes in and supports Equal Employment Opportunity for all employees and does not discriminate in employment opportunities or practices on the basis of race, color, religion, sex, sexual orientation, marital status, national origin, age, disability or any other characteristic protected by law. In order to provide equal employment and advancement opportunities to all individuals, employment decisions at Cumberland will be based on merit, qualification and ability. Each employee will be hired, evaluated, promoted and compensated based on his or her own merit.

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