Entry-Level Medicare Sales Rep

Hirewell; Chicago (IL); On-site; USD 25,000 - 30,000; Full time

Benefits offered by this job

Paid Time Off

Medical Insurance

Dental Insurance

Vision Insurance

Disability Insurance

Life Insurance

401(k) + Company Match

Team events

Job summary

Our Client in downtown Chicago (Willis Tower) seeks an Entry-Level Licensed Benefits Advisor to handle live inbound Medicare inquiries, perform needs-based assessments, and enroll clients in the best-fit plans. Training, licensing, and exam prep are paid, with uncapped bonuses and a full-time in-person schedule.

Ideal candidates are motivated, with strong communication and a willingness to learn, even without prior licensing. Bachelor’s degree is preferred but not required.

Qualifications

• Motivated, goal-oriented and growth-minded.
• Excellent verbal communication and interpersonal skills.
• Sales experience is a plus but not required.

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 coaching and support.
• Guide consumers through enrollment with a service focus.
• Learn and master our insurance product offerings.
• Adhere to CMS and state compliance standards.
• Share feedback with leadership to improve processes.

Skills

Motivated

Strong communicator

Sales experience

Computer skills

Education

Bachelor’s degree preferred

Job description

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.

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.

Additional Benefits:

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

Schedule

Full-Time | Monday–Friday | In Person

Shifts vary by performance and business needs.

• Training shift: 8:30 AM – 5:30 PM (first 4–5 weeks).