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Remote 1099 Insurance Agent Jobs in Chicago, IL (NOW HIRING)

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 ... 1099 independent contractor role ideal for self-motivated individuals seeking control over income ...

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 ... 1099 independent contractor role ideal for self-motivated individuals seeking control over income ...

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 ... 1099 independent contractor role ideal for self-motivated individuals seeking control over income ...

Anderson Johnson Agency

Remote Insurance Agent

Joliet, IL · Remote

$60K - $120K/yr

Comfortable with 1099 commission-based compensation * Strong communication and follow-up skills * Professional, coachable, and self-motivated * Comfortable working remotely and conducting virtual ...

GIA Legacy Planning

Life Insurance Agent

Crown Point, IN · On-site +1

Life Insurance Agent Location: Work from Home Job Type: Full-Time/Part-Time/Commission-Based About ... Flexible work schedule (remote positions) * Comprehensive training and mentorship programs * Access ...

Big I Illinois

Insurance Agent

IL · On-site +1

$60K - $150K/yr

... remote position. Compensation: $60,000.00 - $150,000.00 per year YOUR FUTURE as an Independent ... Insurance Agent Starts Here If you're looking for a career that offers flexibility, job stability ...

Lone Star Careers

Remote Insurance Agent

Chicago, IL · Remote

$69K - $150K/yr

  • Medical

  • Dental

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

HMG Careers

Remote Insurance Agent

Harvey, IL · Remote

$69K/yr

  • Medical

  • Dental

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 ...

Lone Star Careers

Remote Insurance Agent

Gary, IN · Remote

$69K - $150K/yr

  • Medical

  • Dental

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

Promoted2

Remote Insurance Agent

Elk Grove Village, IL · Remote

$69K/yr

  • Medical

  • Dental

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 ...

Promoted2

Remote Insurance Agent

Elgin, IL · Remote

$69K/yr

  • Medical

  • Dental

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 ...

Lone Star Careers

Remote Insurance Agent

Elgin, IL · Remote

$69K - $150K/yr

  • Medical

  • Dental

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

HMG Careers

Remote Insurance Agent

East Chicago, IN · Remote

$69K/yr

  • Medical

  • Dental

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 ...

Promoted2

Remote Insurance Agent

Naperville, IL · Remote

$69K/yr

  • Medical

  • Dental

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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All Jobs1099 Insurance Agent JobsRemote 1099 Insurance Agent JobsRemote 1099 Insurance Agent Jobs in Chicago, IL

Remote 1099 Insurance Agent information

See Chicago, IL salary details

$25.8K

$67K

$125.2K

How much do remote 1099 insurance agent jobs pay per year?

As of Aug 20, 2026, the average yearly pay for remote 1099 insurance agent in Chicago, IL is $66,982.00, according to ZipRecruiter salary data. Most workers in this role earn between $45,800.00 and $79,300.00 per year, depending on experience, location, and employer.

What is a Remote 1099 Insurance Agent?

A Remote 1099 Insurance Agent is an independent contractor who sells insurance policies from a remote location, rather than working onsite at an agency or company office. The '1099' refers to the IRS tax form used for independent contractors, meaning they are not employees but self-employed individuals responsible for their own taxes. These agents typically earn commissions on the policies they sell and have flexibility in setting their own schedules. They often work with multiple insurance companies and must handle their own marketing, client acquisition, and administrative tasks.

What are the key skills and qualifications needed to thrive as a remote 1099 insurance agent?

To thrive as a Remote 1099 Insurance Agent, you need strong sales acumen, comprehensive knowledge of insurance products, and a valid state insurance license. Familiarity with CRM software, quoting systems, and digital communication tools is typically required. Excellent self-motivation, communication, and customer relationship skills help agents stand out in a remote, commission-driven environment. These abilities are crucial for effectively building a client base, meeting sales targets, and succeeding independently in a competitive market.

What are some common challenges faced by remote 1099 insurance agents, and how can they be addressed?

Remote 1099 Insurance Agents often face challenges such as managing their own schedule, generating leads independently, and staying motivated without direct supervision. Building a strong daily routine, leveraging digital marketing strategies, and actively participating in virtual networking or training sessions can help overcome these hurdles. Additionally, effective communication with clients and insurance carriers is crucial, so utilizing reliable technology and CRM tools is highly recommended. Proactively seeking mentorship or support from online agent communities can also provide valuable guidance and encouragement.

What is the difference between Remote 1099 Insurance Agent vs Remote 1099 Insurance Broker?

AspectRemote 1099 Insurance AgentRemote 1099 Insurance Broker
CredentialsLicenses required for specific insurance typesSame as Insurance Agent, plus ability to represent multiple carriers
Work EnvironmentIndependent, remote salesIndependent, remote sales with broader carrier access
Employer/Industry UsageOften contracted directly with insurance companies or agenciesTypically contracted with multiple carriers or as an independent broker
Search/Comparison IntentFocus on individual insurance sales rolesFocus on roles involving multiple carrier representation

While both roles operate remotely as 1099 independent contractors, a Remote 1099 Insurance Agent primarily sells policies for specific insurance companies, requiring relevant licenses. A Remote 1099 Insurance Broker, on the other hand, can represent multiple carriers, offering clients broader options. The key difference lies in carrier access and licensing scope, impacting the sales approach and client offerings.

What are the most commonly searched types of 1099 Insurance Agent jobs in Chicago, IL?

The most popular types of 1099 Insurance Agent jobs in Chicago, IL are:

What are popular job titles related to Remote 1099 Insurance Agent jobs in Chicago, IL?

For Remote 1099 Insurance Agent jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Remote 1099 Insurance Agent jobs in Chicago, IL look for?

The top searched job categories for Remote 1099 Insurance Agent jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Remote 1099 Insurance Agent jobs?

Cities near Chicago, IL with the most Remote 1099 Insurance Agent job openings:

Remote 1099 Insurance Agent jobs near you
Infographic showing various Remote 1099 Insurance Agent job openings in Chicago, IL as of August 2026, with employment types broken down into 77% Full Time, 13% Part Time, and 10% Contract. Highlights an 100% Remote job distribution, with an average salary of $66,982 per year, or $32.2 per hour.

Licensed Life Insurance Agent - Remote | 1099 Commission

Anderson Johnson Agency

Naperville, IL • Remote

$60K - $120K/yr

Full-time, Part-time, Contractor

Re-posted 9 days ago

Job description

The Anderson Johnson Agency is an independent insurance agency focused on protecting families through personalized life insurance solutions. Founded and led by Joe Anderson and Jill Johnson, our agency combines a proven sales system, quality leads, and hands-on mentorship to help licensed agents grow with confidence.

We are selectively adding licensed life 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 opportunity for licensed agents who want access to qualified leads, mentorship, and a proven process without micromanagement.

What You’ll Do
  • Connect with clients who have requested information about life insurance
  • Conduct phone or Zoom appointments
  • Assess client needs and recommend appropriate life insurance solutions
  • Follow up professionally and consistently
  • Use our CRM and virtual sales tools to manage your pipeline
  • Participate in ongoing virtual training and mentorship
What We Provide
  • Qualified leads from people actively looking for life insurance
  • No cold calling or contacting friends and family
  • CRM and virtual sales tools
  • Structured onboarding and ongoing support
  • Mentorship from experienced agency leadership
  • A simple, duplicatable sales process
  • Opportunity to grow within the agency over time
Why Anderson Johnson Agency
  • Mission-driven agency focused on protecting families
  • Mentorship from leaders with 30+ years of experience
  • Recognized for strong agency growth and leadership
  • Top Rookie Agency with over $860,000 in business protected
  • 525% agency growth
  • Supportive culture built around faith, family, ownership, and long-term growth
Qualifications
  • Active life insurance license required
  • U.S.-based applicants only
  • Comfortable with 1099 commission-based compensation
  • Strong communication and follow-up skills
  • Professional, coachable, and self-motivated
  • Comfortable working remotely and conducting virtual appointments
Role Details
  • Position Type: 1099 Independent Contractor
  • Compensation: Commission-based; earnings vary by activity and performance
  • Schedule: Flexible, remote; part-time or full-time
  • Location: Remote, United States

This is not a W-2 position. Earnings are commission-based and dependent on individual effort, consistency, and performance.

  • Job Types: Full-time, Part-time
  • Pay: $60,000–$120,000+ per year
  • Benefits: Work from home
  • Work Location: Remote