EnrollWell
Benefit Counselor
Skills
19 days ago
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Important information
Contract type:
Permanent, Part time
Salary:
$57,000 – $110,000 / year
Location:
Chicago, IL, USA
Work mode:
Hybrid
Published on:
5 October 2026
What they need
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
EnrollWell started as an Aflac operation, built on Aflac's products, training and reputation. As our clients' needs grew, we grew with them. Today we're a Chicago-based, nationally recognized agency specializing in enhanced benefits and enrollment technology. We offer best-in-class products from well-known carriers like Aflac, Transamerica, MassMutual, Unum and many more. We work with local and national companies to add to the benefits they already have and make the whole benefits experience simpler.
Multiple Paths, One Team
- Full-time agent & enroller: Build your career as a full-time Aflac agent, backed by a team that knows the Aflac business inside and out. As you grow, you can also take on broader enrollment work across multiple carriers and larger group accounts.
- Part-time or seasonal large-case enroller: Help enroll employees at larger companies during busy enrollment periods. It's a good fit if you want flexible work without a full-time commitment.
Details and Role Responsibilities
- Business development, sales, and 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!
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.
Job Type: Permanent
Pay: $57,000.00 - $110,000.00 per year
Benefits:
- Flexible schedule
Application Question(s):
- Are you currently an IL resident?
License/Certification:
- Health and/or Life Insurance Producer's License (Preferred)
- Driver's License (Preferred)
Work Location: Hybrid remote in Chicago, IL 60654
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