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Remote Health Insurance Agent Jobs in Chicago, IL

Pitch Health Solutions

Health Insurance Agent

Joliet, IL · Remote

$18 - $20/hr

Remote Health Insurance Agent About Pitch Health Solutions Pitch Health Solutions is a rapidly growing national agency specializing in Medicare Advantage, Final Expense , and more, giving you ...

Pitch Health Solutions

Health Insurance Agent

Aurora, IL · Remote

$18 - $20/hr

Remote Health Insurance Agent About Pitch Health Solutions Pitch Health Solutions is a rapidly growing national agency specializing in Medicare Advantage, Final Expense , and more, giving you ...

Chime Insurance Group

Insurance Agent

Frankfort, IL · Remote

Requirements Sell Life, Health & Medicare coverage remotely with a growing independent agency. 1099 ... Benefits Remote work. $50,000 plus commission Onboard now to start selling by Sept 1 and maximize ...

Promoted2

Remote Insurance Agent

Chicago, IL · Remote

$60K - $110K/yr

Remote Insurance Sales Agent | $60k-$110k+ First Year | No Cold Calling Earn strong first-year income with full training and qualified leads provided - join a fast-growing national financial services ...

Promoted2

Remote Insurance Agent

Gary, IN · Remote

$60K - $110K/yr

Remote Insurance Sales Agent | $60k-$110k+ First Year | No Cold Calling Earn strong first-year income with full training and qualified leads provided - join a fast-growing national financial services ...

Promoted2

Remote Insurance Agent

Chicago, IL · Remote

$60K - $110K/yr

Remote Insurance Sales Agent | $60k-$110k+ First Year | No Cold Calling Earn strong first-year income with full training and qualified leads provided - join a fast-growing national financial services ...

Big I Illinois

Insurance Agent

IL · On-site +1

$60K - $150K/yr

Qualifications: - A life, OR health, OR property and casualty license with at least one year of ... is a remote position. Compensación: $60,000.00 - $150,000.00 per year YOUR FUTURE as an ...

Anderson Johnson Agency

Remote Insurance Agent

Joliet, IL · Remote

$60K - $120K/yr

... insurance agents who are professional, coachable, self-motivated, and interested in building long-term success in a supportive, values-based environment. This is a remote, commission-based ...

HMG Careers

Remote Insurance Agent

Aurora, IL · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

HMG Careers

Remote Insurance Agent

Naperville, IL · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

HMG Careers

Remote Insurance Agent

Gary, IN · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

HMG Careers

Remote Insurance Agent

Elk Grove Village, IL · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

HMG Careers

Remote Insurance Agent

Chicago, IL · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

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Showing results 1-20

All JobsHealth Insurance Agent JobsRemote Health Insurance Agent JobsRemote Health Insurance Agent Jobs in Chicago, IL

Remote Health Insurance Agent information

See Chicago, IL salary details

$25.8K

$67K

$125.3K

How much do remote health insurance agent jobs pay per year?

As of Aug 7, 2026, the average yearly pay for remote health insurance agent in Chicago, IL is $67,035.00, according to ZipRecruiter salary data. Most workers in this role earn between $45,900.00 and $79,400.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a remote health insurance agent?

To thrive as a Remote Health Insurance Agent, you need a comprehensive understanding of health insurance products, strong sales abilities, and a valid state insurance license. Familiarity with customer relationship management (CRM) software, quoting platforms, and telephony systems is typically required. Outstanding communication, self-motivation, and problem-solving skills help agents build trust and effectively address client concerns remotely. These competencies are crucial for meeting sales targets, maintaining regulatory compliance, and delivering exceptional customer service in a virtual work environment.

What is a remote health insurance agent?

A Remote Health Insurance Agent is a licensed professional who helps individuals and businesses select appropriate health insurance plans while working from a remote location, such as their home. They communicate with clients via phone, email, or video calls to understand their needs and present suitable insurance options. Additionally, remote agents assist with policy enrollment, answer questions about coverage, and provide ongoing support. This role typically requires state licensure and strong communication skills. Working remotely allows agents to serve clients across various regions and maintain flexible work schedules.

What is the best insurance company to work for remotely?

For remote health insurance agents, companies like UnitedHealth Group, Cigna, and Humana are known for offering remote positions with flexible schedules and comprehensive training. These companies often provide competitive pay, benefits, and opportunities for career advancement in a remote work environment.

What is the difference between Remote Health Insurance Agent vs Remote Life Insurance Agent?

AspectRemote Health Insurance AgentRemote Life Insurance Agent
Required CertificationsHealth insurance licenses, certifications in health plansLife insurance licenses, certifications in life policies
Work EnvironmentRemote, customer service, salesRemote, sales, client consultations
Employer & Industry UsageHealth insurance providers, brokersLife insurance providers, brokers
Search & Comparison IntentCompare health insurance options, licensingCompare life insurance policies, licensing

Remote Health Insurance Agents focus on health plans and require health insurance licenses, while Remote Life Insurance Agents specialize in life policies and hold relevant life insurance licenses. Both roles are remote, customer-focused, and common in insurance brokerages, but they serve different insurance sectors.

How do remote health insurance agents typically collaborate with team members and clients while working from home?

Remote Health Insurance Agents often use a mix of digital tools, such as video conferencing, instant messaging, and cloud-based CRM platforms, to stay connected with both clients and colleagues. Regular virtual meetings and training sessions help agents stay updated on policy changes and sales strategies. Effective communication and timely follow-ups are essential, as most client interactions happen via phone or online channels. Team collaboration is crucial for sharing leads, discussing challenging cases, and ensuring compliance with regulations, all while maintaining a high level of customer service remotely.
What are the most commonly searched types of Health Insurance Agent jobs in Chicago, IL? The most popular types of Health Insurance Agent jobs in Chicago, IL are:
What are popular job titles related to Remote Health Insurance Agent jobs in Chicago, IL? For Remote Health Insurance Agent jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Remote Health Insurance Agent jobs in Chicago, IL look for? The top searched job categories for Remote Health Insurance Agent jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Remote Health Insurance Agent jobs? Cities near Chicago, IL with the most Remote Health Insurance Agent job openings:
Remote Health Insurance Agent jobs near you
Infographic showing various Remote Health Insurance Agent job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 76% Full Time, 18% Part Time, and 5% Contract. Highlights an 96% Physical, 1% Hybrid, and 3% Remote job distribution, with an average salary of $67,035 per year, or $32.2 per hour.

Health Insurance Agent

Pitch Health Solutions

Schaumburg, IL • Remote

$18 - $20/hr

Full-time

Re-posted 25 days ago

Job description

Remote Health Insurance Agent

About Pitch Health Solutions

Pitch Health Solutions is a rapidly growing national agency specializing in Medicare Advantage, Final Expense, and more, giving you unlimited opportunities to grow, maximize commissions, and build a long-term career in the industry.

We reward drive, professionalism, and consistency. If you're ambitious, coachable, and ready to grow, this is the perfect place to elevate your career.
This job is fully remote.

Your Path With Us
Step 1: Start of Employment (Transfer Agent Role)

Start your journey with a paid 2 to 4 week onboarding program where you will:

  • Use our dialer to outbound connect pre-qualified seniors with licensed agentsGain real-time call experience and confidence
  • Complete your carrier contracting & certifications
  • Receive hands-on coaching from industry experts

Once your contracting is complete, you’ll seamlessly transition to the next phase.

Step 2: Medicare & Senior Benefits Specialist

After onboarding, you will step into a fully active sales role with:

  • 100% inbound calls, no cold calling, no hunting, no chasing
  • A steady flow of interested, qualified prospects from our in-house marketing team
  • Live client transfers from individuals ready to explore Medicare or Final Expense coverage
  • The bandwidth to focus solely on what matters: connecting, educating, and closing

We do the marketing. We handle lead generation.You focus on serving clients and winning daily.
Compensation & Perks

Start of Employment (Transfer Agent Role)

Kick off your journey with a strong foundation and guaranteed earnings while you train:

  • $18/hour base pay, plus commissions per transfer
  • Paid 2 to 4 week onboarding with live call training and real call experience
  • Full-time schedule: Monday to Friday, from 9 AM till 6 PM EST (occasional Saturdays)
  • Includes a 1-hour lunch break
  • 100% Remote: Work from anywhere nationwide
  • Hands-on coaching, skill-building, and a clear path to promotion into your Medicare @Specialist role


Medicare & Senior Benefits Specialist

Unlock your full earning potential once you transition into active inbound sales:

  • $18–$20/hour base pay (based on experience)
  • Lucrative, performance-driven commissions
    • Top-performing Specialists consistently earn $2,000–$3,000 per week
  • All inbound calls — no cold calling, ever
  • Full-time schedule: Monday to Friday, from 9 AM till 6 PM EST (occasional Saturdays)
  • Includes a 1-hour lunch break
  • 100% Remote: Earn nationwide from the comfort of your home
  • Endless growth opportunities in a rapidly expanding organization

What You’ll Do as an Active Sales Agent

  • Handle qualified inbound calls (no dialing, no chasing)
  • Sell Medicare and Final Expense plans
  • Educate seniors, guide them through their options, and enroll them in coverage
  • Meet sales goals while maintaining compliance and professionalism

What We’re Looking For

  • Active health insurance license — licensed in 7+ states is a plus
  • 1+ year of insurance sales experience preferred (not required)
  • Strong closer with excellent communication skills
  • Coachable, motivated, and results-driven
  • Tech-ready: PC/laptop (i5+, 8GB RAM), wired internet, USB headset

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