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Entry Level Medicare Sales 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 ...

My Senior Health Plan

Sales Representative

Brentwood, TN · On-site

$57K - $107K/yr

My Senior Health Plan, a leader in the Medicare B2C space for nearly 20 years, is looking for a motivated and energetic Entry Level Sales Representative to join our growing team in Brentwood, TN. If ...

My Senior Health Plan

Sales Representative

Brentwood, TN · On-site

$57K - $107K/yr

My Senior Health Plan, a leader in the Medicare B2C space for nearly 20 years, is looking for a motivated and energetic Entry Level Sales Representative to join our growing team in Brentwood, TN. If ...

My Senior Health Plan

Sales Representative

La Jolla, CA · On-site

$21 - $24/hr

My Senior Health Plan, a leader in the Medicare B2C space for nearly 20 years, is looking for a motivated and energetic Entry Level Sales Representative to join our growing team in La Jolla, CA. If ...

My Senior Health Plan

Sales Representative

La Jolla, CA · On-site

$57K - $107K/yr

My Senior Health Plan, a leader in the Medicare B2C space for nearly 20 years, is looking for a motivated and energetic Entry Level Sales Representative to join our growing team in La Jolla, CA. If ...

My Senior Health Plan

Sales Representative

La Jolla, CA · On-site

$57K - $107K/yr

My Senior Health Plan, a leader in the Medicare B2C space for nearly 20 years, is looking for a motivated and energetic Entry Level Sales Representative to join our growing team in La Jolla, CA. If ...

EMERGE

Entry-Level Health Insurance Sales Agent

Chicago, IL · On-site

$55K - $75K/yr

... Medicare guidance and support to seniors. Located in downtown Chicago, this team-driven, in-office ... This entry-level Sales Specialist role will equip you with the tools and resources to succeed. All ...

New

The Juris Agency

Entry Level - Inside Sales

Austin, TX · On-site

$60 - $80/hr

Bell Brokerage Group is a fast-growing independent Medicare and health brokerage looking for motivated, coachable sales pros. Work with multiple carriers, get hands-on mentorship, and grow with a ...

EMERGE

Inside Sales Representative

Chicago, IL · On-site

$55K - $75K/yr

... Medicare guidance and support to seniors. Located in downtown Chicago, this team-driven, in-office ... This entry-level Sales Specialist role will equip you with the tools and resources to succeed. All ...

EMERGE

Inside Sales Representative

Chicago, IL · On-site

$55K - $75K/yr

... Medicare guidance and support to seniors. Located in downtown Chicago, this team-driven, in-office ... This entry-level Sales Specialist role will equip you with the tools and resources to succeed. All ...

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All Jobsmedicare sales JobsEntry Level Medicare Sales Jobs

Entry Level Medicare Sales information

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$22K

$45K

$65K

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

As of Sep 7, 2026, the average yearly pay for entry level medicare sales in the United States is $45,046.00, according to ZipRecruiter salary data. Most workers in this role earn between $37,000.00 and $50,000.00 per year, depending on experience, location, and employer.

What is an entry level Medicare sales representative?

An Entry Level Medicare Sales job involves helping clients understand and enroll in Medicare plans, such as Medicare Advantage, Medicare Supplement, or Prescription Drug Plans. Professionals in this role educate clients about their Medicare options, assess their healthcare needs, and guide them through the application process. Entry-level positions typically require strong communication and customer service skills, as well as the ability to explain complex insurance products. Many employers provide training and may require state health insurance licensure. This role is ideal for individuals looking to start a career in health insurance sales.

What are the key skills and qualifications needed to thrive as an entry level Medicare sales representative?

To thrive as an Entry Level Medicare Sales representative, you need a solid understanding of Medicare products, basic sales techniques, and typically a high school diploma or equivalent. Familiarity with CRM systems, quoting tools, and obtaining state health insurance licenses (such as an accident and health or sickness license) are commonly required. Strong interpersonal communication, active listening, and resilience help you build trust with clients and overcome objections. These skills and qualifications are crucial to effectively match clients with appropriate Medicare plans and achieve sales targets in a regulated industry.

What are some common challenges faced by entry level Medicare sales representatives, and how can they be overcome?

Entry-level Medicare sales representatives often encounter challenges such as navigating complex insurance regulations, understanding multiple plan options, and building trust with clients who may be unfamiliar with Medicare details. Overcoming these challenges typically involves ongoing training, seeking mentorship from experienced team members, and utilizing company-provided resources to stay updated on policy changes. Proactive communication, patience, and a willingness to learn are essential for success and growth in this role.

What is the difference between Entry Level Medicare Sales vs Entry Level Health Insurance Sales?

AspectEntry Level Medicare SalesEntry Level Health Insurance Sales
Required CertificationsMedicare certification, health insurance licenseHealth insurance license, general insurance certification
Work EnvironmentInsurance agencies, healthcare providers, insurance brokersInsurance agencies, brokerages, online sales platforms
Employer & Industry UsagePrimarily in healthcare and insurance sectors focusing on Medicare productsBroader insurance industry, including health, life, and disability insurance

Entry Level Medicare Sales and Entry Level Health Insurance Sales share similar certifications and work environments, often employed by insurance agencies or brokers. However, Medicare Sales specifically targets seniors and healthcare plans, while Health Insurance Sales covers a broader range of insurance products. Understanding these differences helps job seekers align their skills with the right role in the insurance industry.

How to become an entry level Medicare sales agent with no experience?

To become an entry-level Medicare sales agent, you typically need a high school diploma or equivalent and must complete a state licensing exam for health insurance. No prior experience is required, but strong communication skills and knowledge of Medicare plans are helpful; some employers provide training. Obtaining a license and understanding federal and state regulations are essential steps in starting this role.
More about Entry Level Medicare Sales jobs

What cities are hiring for Entry Level Medicare Sales jobs?

Cities with the most Entry Level Medicare Sales job openings:

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

The most popular types of Medicare Sales jobs are:

What states have the most Entry Level Medicare Sales jobs?

States with the most job openings for Entry Level Medicare Sales jobs include:

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

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

Entry Level Medicare Sales jobs near you
Infographic showing various Entry Level Medicare Sales 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 $45,046 per year, or $21.7 per hour.

Entry-Level Medicare Sales Rep

Hirewell

Chicago, IL • On-site

$20/hr

Other

Medical, Dental, Vision, Life, Retirement, PTO

Posted 8 days ago

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)


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