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Entry Level Insurance Agent Training Program Jobs in Chicago, IL

Pitch Health Solutions

Health Insurance Agent

Chicago, IL · Remote

$18 - $20/hr

... program where you will: * Use our dialer to outbound connect pre-qualified seniors with licensed ... Paid 2 to 4 week onboarding with live call training and real call experience * Full-time schedule:

Pitch Health Solutions

Health Insurance Agent

Joliet, IL · Remote

$18 - $20/hr

... program where you will: * Use our dialer to outbound connect pre-qualified seniors with licensed ... Paid 2 to 4 week onboarding with live call training and real call experience * Full-time schedule:

Pitch Health Solutions

Health Insurance Agent

Aurora, IL · Remote

$18 - $20/hr

... program where you will: * Use our dialer to outbound connect pre-qualified seniors with licensed ... Paid 2 to 4 week onboarding with live call training and real call experience * Full-time schedule:

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All JobsInsurance Agent Training Program JobsEntry Level Insurance Agent Training Program JobsEntry Level Insurance Agent Training Program Jobs in Chicago, IL

Entry Level Insurance Agent Training Program information

See Chicago, IL salary details

$25.8K

$67K

$125.2K

How much do entry level insurance agent training program jobs pay per year?

As of Jun 9, 2026, the average yearly pay for entry level insurance agent training program 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 the difference between Entry Level Insurance Agent Training Program vs Insurance Sales Associate?

AspectEntry Level Insurance Agent Training ProgramInsurance Sales Associate
Required CredentialsHigh school diploma or equivalent; licensing required post-trainingHigh school diploma or equivalent; licensing often required
Work EnvironmentClassroom training, mentorship, and fieldworkOffice or retail environment, direct customer interaction
Employer & Industry UsageInsurance companies, agencies, and brokeragesInsurance agencies, brokerages, and direct sales roles
Common Search & ComparisonTraining programs for new agentsEntry-level sales roles in insurance

The Entry Level Insurance Agent Training Program focuses on preparing individuals through structured training and licensing, often with a mentorship component. In contrast, an Insurance Sales Associate typically involves direct sales and customer service in an office or retail setting. Both roles require licensing and are common entry points into the insurance industry, but the training program emphasizes education and skill development before active sales duties.

What are the most commonly searched types of Insurance Agent Training Program jobs in Chicago, IL? The most popular types of Insurance Agent Training Program jobs in Chicago, IL are:
Entry Level Insurance Agent Training Program jobs near you
Infographic showing various Entry Level Insurance Agent Training Program job openings in Chicago, IL as of June 2026, with employment types broken down into 75% Full Time, and 25% Part Time. Highlights an 87% In-person, and 13% Remote job distribution, with an average salary of $66,982 per year, or $32.2 per hour.

Insurance Sales Agent - Customer Service

Freeway Insurance

West Chicago, IL

Full-time

Medical, Dental, Vision, Life, Retirement

Posted 23 days ago

Freeway Insurance rating

8.0

Company rating: 8.0 out of 10

Based on 10 frontline employees who took The Breakroom Quiz

145th of 260 rated insurance

Job description

Our Perks:

  • Unlimited/Uncapped commission
  • Lucrative incentive sales plans, bonuses and sales contests
  • No Cold Calling- We have a high volume of inbound sales leads and walk in traffic
  • Comprehensive paid training and licensing with continuous on-going training and mentorship
  • Recognition culture
  • Comprehensive Benefits package including medical, dental, vision and life insurance
  • Retirement Plan: A 401K plan with a percentage of company-matched contributions
  • Fitness: Discount gym membership to over 12,200 fitness centers and 9,300 on-demand workout videos including a $15 a month reimbursement.
  • Employee Assistance Program: Confidential assistance to you or anyone in your household who is experiencing personal or professional problems — at no cost
  • Extra Perks: Access to disability, hospital indemnity, health advocate program, universal life, critical illness, and accident insurance plans. We even offer pet insurance

Our Company:

Confie and its family of companies - Freeway, Baja, Bluefire & others - is one of the largest privately held insurance brokers in the United States and has been ranked the #1 Personal Lines Leader by the Insurance Journal for the seventh straight year!. With over 800 retail store locations to choose from nationwide, we encourage you to take your career and income potential to new heights! We are proactively looking for bright, talented, and motivated individuals who are goal oriented and excited for career advancement. Come Grow With Us!

What You Will Do:

As an Insurance Agent you will be responsible primarily for the sale of nonstandard auto insurance to new and existing customers.

  • Solicit new business and maintain current business levels in order to achieve or exceed sales production goals.
  • Expand business by proactively building relationships with existing customers to meet the agreed upon production goals.
  • Accurate accounting of all currency transactions as well as timely delivery of deposits to the bank with scanned documentation in agency management system.
  • Connects very quickly; builds and leverages client relationships. Ability to educate and advise the customer on which products best fit their needs

The Perfect Match:

  • Personal Lines or Property and Casualty license preferred (but not required)
  • Bilingual in English and Spanish preferred
  • Sales or customer service experience
  • High School Diploma or GED
  • Ability to build relationships with sales customers
  • Excellent follow-up and multi-tasking skills
  • Ambitious professional motivated by opportunity for advancement
  • Excellent written and verbal communication skills

Insurance Sales
Insurance Agent
Hiring Immediately
Freeway Auto Insurance

As permitted by applicable law and from time-to-time, Confie may use a computer system that has elements of artificial intelligence to help make decisions about your employment, including recruitment, hiring, renewal of employment, or the terms and conditions of your employment. Employees with questions about Confie’s use of these computer systems should contact Human Resources at employeerelations@confie.com  

What Freeway Insurance employees say

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Hours and flexibility

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