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Weekend Insurance Agent Jobs in Naperville, IL (NOW HIRING)

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Licensed Insurance Agent- Yorkville, IL

Yorkville, IL · On-site

$40K - $45K/yr

The Licensed Insurance Agent will assist clients with personal and commercial insurance needs while providing excellent customer service and policy support. This role requires strong communication ...

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All JobsInsurance Agent JobsWeekend Insurance Agent JobsWeekend Insurance Agent Jobs in Naperville, IL

Weekend Insurance Agent information

See Naperville, IL salary details

$25K

$64.9K

$121.3K

How much do weekend insurance agent jobs pay per year?

As of Aug 7, 2026, the average yearly pay for weekend insurance agent in Naperville, IL is $64,925.00, according to ZipRecruiter salary data. Most workers in this role earn between $44,400.00 and $76,900.00 per year, depending on experience, location, and employer.

Why do so many weekend insurance agents quit?

Weekend insurance agents often leave the role due to limited hours, lower pay, and lack of career advancement opportunities. The part-time schedule can also lead to job insecurity and difficulty balancing work with personal commitments, contributing to higher turnover rates.

Do weekend insurance agents work on weekends?

Weekend insurance agents typically work during weekends as part of their schedule, especially if they serve clients who are available outside regular weekday hours. Their work may include handling claims, providing customer service, or selling policies, often requiring flexibility to meet client needs. The specific schedule depends on the employer and the role's responsibilities.

What is the difference between Weekend Insurance Agent vs Part-Time Insurance Agent?

AspectWeekend Insurance AgentPart-Time Insurance Agent
CredentialsLicensing required, similar certificationsLicensing required, similar certifications
Work EnvironmentPrimarily weekend hours, flexible scheduleFlexible hours, may include weekdays and weekends
Employer & Industry UsageInsurance agencies, brokersInsurance agencies, brokers
Search & Comparison IntentFocus on weekend availability and part-time rolesBroader part-time roles, including weekdays

Weekend Insurance Agents typically work primarily on weekends, offering flexible scheduling for clients. Part-Time Insurance Agents may work during weekdays or weekends, with varied hours. Both roles require similar licensing and certifications, but the main difference lies in their scheduling focus and availability.

What are the most commonly searched types of Insurance Agent jobs in Naperville, IL? The most popular types of Insurance Agent jobs in Naperville, IL are:
What are popular job titles related to Weekend Insurance Agent jobs in Naperville, IL? For Weekend Insurance Agent jobs in Naperville, IL, the most frequently searched job titles are:
What job categories do people searching Weekend Insurance Agent jobs in Naperville, IL look for? The top searched job categories for Weekend Insurance Agent jobs in Naperville, IL are:
What cities near Naperville, IL are hiring for Weekend Insurance Agent jobs? Cities near Naperville, IL with the most Weekend Insurance Agent job openings:
Weekend Insurance Agent jobs near you
Infographic showing various Weekend Insurance Agent job openings in Naperville, IL as of August 2026, with employment types broken down into 1% As Needed, 74% Full Time, 20% Part Time, and 5% Contract. Highlights an 91% Physical, 1% Hybrid, and 8% Remote job distribution, with an average salary of $64,925 per year, or $31.2 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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