Inside Sales Representative

Hirewell
Chicago, IL

Our Client is growing rapidly, and we’re looking for driven, motivated individuals to join our inside sales team. As an Entry-Level Licensed Benefits Advisor, you’ll take live inbound calls from individuals exploring their Medicare options, guide them through a needs-based assessment, and help them enroll in the plan that best fits their needs.

No insurance license? We pay for your training, licensing, and exam prep.

This is an in-office role located in downtown Chicago at the Willis Tower.

Responsibilities

  • Take live, inbound consumer calls and recommend Medicare plan options.
  • Conduct outbound follow-ups to our book of business.
  • Meet monthly sales goals with strong support and coaching.
  • Guide consumers through enrollment with a focus on world-class service.
  • Learn and master our insurance product offerings.
  • Adhere to all CMS and state compliance standards.
  • Share feedback with leadership to improve processes.

Qualifications

  • Motivated, goal-oriented, and ready to grow in a fast-paced environment.
  • Strong communicator with solid interpersonal skills.
  • Sales experience is a plus—but not required.
  • Comfortable using computers and multiple screens.
  • Ability to complete licensing and background requirements.
  • Bachelor’s degree preferred but not required.

Compensation and Benefits

  • $20.00/hr base pay
  • Uncapped monthly bonuses.
  • Overtime incentives available during Annual Enrollment Period (Oct 15–Dec 7).

Additional Benefits:

  • Paid Time Off (PTO).
  • Medical, Dental, and Vision.
  • Short- & Long-Term Disability and Life Insurance.
  • 401(k) + Company Match.
  • Commuter Benefits.
  • Professional development & internal growth paths.
  • Fun, competitive, and supportive team environment.
  • Team outings & company-sponsored events.

Schedule



Full-Time | Monday–Friday | In Perso

nShifts vary by performance and business needs

  • .Training shift: 8:30 AM – 5:30 PM (first 4–5 weeks)
  • .Possible shifts after training
  • :8:00 AM – 5:00 P
  • M8:30 AM – 5:30 P
  • M9:00 AM – 6:00 P
  • M9:30 AM – 6:30 PM (Oct–Dec only
  • )10:00 AM – 7:00 PM (Oct–Dec only


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