Find a jobRecruiters

Benefit Counselor

Exclusive opportunity

Hybrid

Benefit Counselor

EnrollWell

Benefit Counselor

Skills

Business Development

19 days ago

Share this opportunity

Share this opportunity to other talents of your network:
✓ Offer them a visibility boost with clients.
✓ Help your contacts find their next job.

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

Other offers great for you!

These companies are also looking for great profiles

Innova Solutions

Développeur(se) .NET/ React

Entre 43K et 50K brut annuel

Permanent contract

Nice, France

Hybrid

Skills

.NET.net coreReact

9 hours ago

Quick apply

Neonum

Directeur de Projet SI / Scrum – Migration Genesys vers Amazon Connect (CCaaS)

800-900 € HT selon profil

Freelance

Paris, France

Hybrid

Top Recruiter

Skills

PMOTéléphonieCCaaSAmazon ConnectGenesys

8 hours ago

Quick apply

Meetshake

Analyst SOC

Freelance

Paris, France

Hybrid, Onsite

Skills

SIEMEDR/XDRSOARSecurity incident analysisThreat huntingMITRE ATT&CK

7 hours ago

Quick apply

The best place to find your next move

© 2026. All Rights Reserved.

Talents

Find a job

Create a profile

Solutions and tools