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The EnrollWell Opportunity


  • Business to Business benefits consulting and sales

  • Team-based structure and mentorship culture

  • Growth opportunities and upward mobility

  • Ongoing training and professional development

  • Flexible schedule and hybrid work model

  • Best in class compensation with residual income vesting

  • Insurance industry experience not required

Watch to learn more:

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Position Description

Why EnrollWell and Why Now?

With the demand for benefits in the workplace never higher due to an ever-changing health insurance landscape, EnrollWell is expanding and in search of Benefit Counselors to service our growing market. Given the dramatic cost and decreased coverage of health insurance, companies are in desperate need of benefits to fill the gaps and address challenges with attracting and retaining employees. We work with both local and national companies to supplement what is already in place while streamlining the overall benefits experience.

About Us

We are a Chicago-based, nationally recognized agency specializing in enhanced benefits and enrollment technology solutions. We offer best-in-class products and services from well-known carriers like Aflac, Transamerica, Mass Mutual, Unum, and many more.

Details and Role Responsibilities

• Business development, sales, and customer relationship management (B2B)

• No door-to-door individual sales involved

• No experience in the insurance space required

• Extensive up-front training is provided

• Ongoing training and professional development with upward mobility and growth

• Team-first culture and mentorship model

• Licensing reimbursement is offered


If you have the desire to join a winning team and are looking for an opportunity to be a part of the fastest growing segment of the insurance industry, please contact us to learn more about the role. At EnrollWell, we believe in better living through benefits!

*Must be 18 years of age or older and authorized to work in the United States. We are unable to sponsor a work visa at this time, nor can we accommodate relocation costs.

*Valid Driver's License and access to a vehicle is strongly preferred.

*Hiring is for our physical office in Chicago, IL. Please note we are NOT offering fully remote positions currently.

EnrollWell is an Equal Opportunity Employer and we do not discriminate on the basis of race, creed, color, ethnicity, national origin, religion, sex, sexual orientation, gender expression, or any other status.

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