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Entry Level Medicare Sales Supervisor Jobs (NOW HIRING)

Hirewell

Entry-Level Medicare Sales Rep

Chicago, IL · On-site

$20/hr

... 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 ...

New

Lthc

Medicare Sales Advocate I

Dewitt, MI · Remote

The Medicare Sales Advocate (MSA) is responsible for finding Medicare solutions for beneficiaries ... Supervisor, the fraud and abuse hotline, the Compliance Officer, the Compliance Director, Human ...

Lthc

Medicare Sales Advocate I

Utica, NY · Remote

The Medicare Sales Advocate (MSA) is responsible for finding Medicare solutions for beneficiaries ... Supervisor, the fraud and abuse hotline, the Compliance Officer, the Compliance Director, Human ...

Lthc

Medicare Sales Advocate I

Buffalo, NY · Remote

The Medicare Sales Advocate (MSA) is responsible for finding Medicare solutions for beneficiaries ... Supervisor, the fraud and abuse hotline, the Compliance Officer, the Compliance Director, Human ...

Lthc

Medicare Sales Advocate I

Albany, NY · Remote

The Medicare Sales Advocate (MSA) is responsible for finding Medicare solutions for beneficiaries ... Supervisor, the fraud and abuse hotline, the Compliance Officer, the Compliance Director, Human ...

Lthc

Medicare Sales Advocate I

Dewitt, MI · Remote

The Medicare Sales Advocate (MSA) is responsible for finding Medicare solutions for beneficiaries ... Supervisor, the fraud and abuse hotline, the Compliance Officer, the Compliance Director, Human ...

Lthc

Medicare Sales Advocate I

Utica, NY · Remote

The Medicare Sales Advocate (MSA) is responsible for finding Medicare solutions for beneficiaries ... Supervisor, the fraud and abuse hotline, the Compliance Officer, the Compliance Director, Human ...

Lthc

Medicare Sales Advocate I

Binghamton, NY · Remote

The Medicare Sales Advocate (MSA) is responsible for finding Medicare solutions for beneficiaries ... Supervisor, the fraud and abuse hotline, the Compliance Officer, the Compliance Director, Human ...

Lthc

Medicare Sales Advocate I

Buffalo, NY · Remote

The Medicare Sales Advocate (MSA) is responsible for finding Medicare solutions for beneficiaries ... Supervisor, the fraud and abuse hotline, the Compliance Officer, the Compliance Director, Human ...

Lthc

Medicare Sales Advocate I

Rochester, NY · Remote

The Medicare Sales Advocate (MSA) is responsible for finding Medicare solutions for beneficiaries ... Supervisor, the fraud and abuse hotline, the Compliance Officer, the Compliance Director, Human ...

Lthc

Medicare Sales Advocate I

Albany, NY · Remote

The Medicare Sales Advocate (MSA) is responsible for finding Medicare solutions for beneficiaries ... Supervisor, the fraud and abuse hotline, the Compliance Officer, the Compliance Director, Human ...

Lthc

Medicare Sales Advocate I

Rochester, NY · Remote

The Medicare Sales Advocate (MSA) is responsible for finding Medicare solutions for beneficiaries ... Supervisor, the fraud and abuse hotline, the Compliance Officer, the Compliance Director, Human ...

Lthc

Medicare Sales Advocate I

Utica, NY · Remote

The Medicare Sales Advocate (MSA) is responsible for finding Medicare solutions for beneficiaries ... Supervisor, the fraud and abuse hotline, the Compliance Officer, the Compliance Director, Human ...

Lthc

Medicare Sales Advocate I

Binghamton, NY · Remote

The Medicare Sales Advocate (MSA) is responsible for finding Medicare solutions for beneficiaries ... Supervisor, the fraud and abuse hotline, the Compliance Officer, the Compliance Director, Human ...

Lthc

Medicare Sales Advocate I

Albany, NY · Remote

The Medicare Sales Advocate (MSA) is responsible for finding Medicare solutions for beneficiaries ... Supervisor, the fraud and abuse hotline, the Compliance Officer, the Compliance Director, Human ...

Lthc

Medicare Sales Advocate I

Dewitt, MI · Remote

The Medicare Sales Advocate (MSA) is responsible for finding Medicare solutions for beneficiaries ... Supervisor, the fraud and abuse hotline, the Compliance Officer, the Compliance Director, Human ...

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All JobsBusiness JobsSales JobsMedical Sales Associate JobsEntry Level Medicare Sales Supervisor Jobs

Entry Level Medicare Sales Supervisor information

See salary details

$27.5K

$75.8K

$142.5K

How much do entry level medicare sales supervisor jobs pay per year?

As of Sep 3, 2026, the average yearly pay for entry level medicare sales supervisor in the United States is $75,848.00, according to ZipRecruiter salary data. Most workers in this role earn between $45,000.00 and $96,500.00 per year, depending on experience, location, and employer.

What is the difference between Entry Level Medicare Sales Supervisor vs Medicare Sales Representative?

AspectEntry Level Medicare Sales SupervisorMedicare Sales Representative
CredentialsHigh school diploma or equivalent; sales experience; sometimes certifications in health insuranceHigh school diploma or equivalent; health insurance licensing often required
Work EnvironmentSupervisory role overseeing sales teams, often in office or remote settingsDirect sales to clients, in person or via phone/online
Employer & Industry UsageInsurance companies, health plans, brokersInsurance agencies, health plans, brokers
Search & Comparison IntentUnderstanding entry-level supervisory roles in Medicare salesEntry-level sales roles in Medicare insurance

While both roles involve Medicare insurance sales, the Entry Level Medicare Sales Supervisor oversees sales teams and strategies, whereas the Medicare Sales Representative focuses on direct client sales. The supervisor role typically requires some experience and leadership skills, while the representative role emphasizes direct customer interaction and sales skills.

More about Entry Level Medicare Sales Supervisor jobs

What are the most commonly searched types of Medicare Sales Supervisor jobs?

The most popular types of Medicare Sales Supervisor jobs are:

What job categories do people searching Entry Level Medicare Sales Supervisor jobs look for?

The top searched job categories for Entry Level Medicare Sales Supervisor jobs are:

Entry Level Medicare Sales Supervisor jobs near you
Infographic showing various Entry Level Medicare Sales Supervisor job openings in the United States as of August 2026, with employment types broken down into 80% Full Time, 19% Part Time, and 1% Contract. Highlights an 84% Physical, 1% Hybrid, and 15% Remote job distribution, with an average salary of $75,848 per year, or $36.5 per hour.

Entry-Level Medicare Sales Rep

Hirewell

Chicago, IL • On-site

$20/hr

Other

Medical, Dental, Vision, Life, Retirement, PTO

Posted 3 days ago

New

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.


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 Person

Shifts 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 PM
  • 8:30 AM – 5:30 PM
  • 9:00 AM – 6:00 PM
  • 9:30 AM – 6:30 PM (Oct–Dec only)
  • 10:00 AM – 7:00 PM (Oct–Dec only)


Apply