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Entry Level Insurance Agent Training Program Jobs in Chicago, IL

HealthMarkets, Inc.

Insurance Sales Agent

Joliet, IL · On-site

We provide you with the support, training, and resources you need to succeed on your terms. Get ... An Independent licensed insurance agent with HealthMarkets is a commission only opportunity.

Big I Illinois

Insurance Agent

IL · On-site +1

$60K - $150K/yr

We have systems, training, vendors, mentorship, best practices, and more to support you in that ... Compensation: $60,000.00 - $150,000.00 per year YOUR FUTURE as an Independent Insurance Agent ...

StaffMyAgency LLC

Insurance Agent

Mundelein, IL · On-site

$40K - $70K/yr

This program offers a unique opportunity to learn the insurance business from the inside out while working directly with a successful mentor agent. You'll gain hands-on experience, extensive training ...

Globe Life Insurance

Be Seen First

Entry Level Insurance Sales Representative (100% Remote)

Chicago, IL · Remote

$60K - $80K/yr

Training and ongoing coaching are provided to help new representatives learn the products, systems, and client process. Instead of spending the day making unsolicited calls, representatives connect ...

Globe Life Insurance

Be Seen First

Entry Level Insurance Sales Representative (100% Remote)

Naperville, IL · Remote

$60K - $80K/yr

Training and ongoing coaching are provided to help new representatives learn the products, systems, and client process. Instead of spending the day making unsolicited calls, representatives connect ...

Globe Life Insurance

Be Seen First

Entry Level Insurance Sales Representative (100% Remote)

Chicago, IL · Remote

$60K - $80K/yr

Training and ongoing coaching are provided to help new representatives learn the products, systems, and client process. Instead of spending the day making unsolicited calls, representatives connect ...

Globe Life Insurance

Be Seen First

Entry Level Insurance Sales Representative (100% Remote)

Naperville, IL · Remote

$60K - $80K/yr

Training and ongoing coaching are provided to help new representatives learn the products, systems, and client process. Instead of spending the day making unsolicited calls, representatives connect ...

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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 Sep 12, 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.

Do entry level insurance agents get paid during training?

Entry level insurance agents typically do not receive a salary during training, as training programs often focus on education and skill development. However, some companies may offer a stipend, commission-based pay, or a combination of both once training is completed and agents begin selling policies. Compensation structures vary by employer and program.

How to be an entry level insurance agent training program with no experience?

To join an entry level insurance agent training program with no experience, applicants typically need a high school diploma or equivalent and must pass licensing exams for the specific insurance types they wish to sell. Many programs provide on-the-job training, sales techniques, and product knowledge, making prior experience unnecessary. Strong communication skills and a willingness to learn are important for success in these programs.

What is the minimum qualification to become an entry level insurance agent training program?

Entry level insurance agent training programs typically require applicants to have a high school diploma or equivalent. Candidates must also pass a licensing exam and often complete pre-licensing education courses before starting the program.

Why do so many entry level insurance agents quit?

Entry level insurance agents often quit due to challenges in building a client base, inconsistent income, and high rejection rates. The job requires strong sales skills, persistence, and the ability to handle rejection, which can be difficult for new agents to sustain over time.

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 September 2026, with employment types broken down into 100% Full Time. Highlights an 100% In-person job distribution, with an average salary of $66,982 per year, or $32.2 per hour.

Insurance Agent - South Holland, IL

South Holland, IL • On-site

NACBA
See more jobs at NACBAexternal

Other

Posted 6 days ago

Job description

Community leader. Protector of dreams. That's what it means to be an American Family Insurance Agent! It's a highly rewarding opportunity that allows you to create financial stability while making a positive impact on our customers' lives. If you're looking for a chance to own your future — we're interested in you!

We're not simply looking for "salespeople" to become Agents. We're searching for passionate relationship builders—people who are ready to make a real impact in their community, provide exceptional care to our customers, and build something truly amazing!

Our Talent Acquisition team reviews every application and connects with qualified candidates to start the conversation.

Agents operate as independent contractors, representing American Family and its products exclusively. As an Insurance Agent, you'll be responsible for your agency's overall management, sales, and growth. You'll also hire your team and work with them to meet the strategic business goals you set.

Reasons why you should become an American Family Insurance Agent:

  • Financially Fit: American Family has the financial security to protect the dreams of your policyholders

  • Fortune 500 company that is among the largest Property and Casualty insurance groups

  • Offer American Family Insurance products as well as products and services through our subsidiary partners

  • Training and support from a local team from marketing, prospecting, business consultation and more

  • Unlimited compensation potential including a New Agent Incentive Program

Requirements

  • Obtain Property and Casualty and Life and Health insurance licenses

  • Ability to pass a motor vehicle, financial/credit and criminal background check

We believe people are an organization's most valuable asset, and their ideas and experiences matter. From our CEO to our agency force, we're committed to growing a diverse and inclusive culture that empowers innovation that will inspire, protect, and restore our customers' dreams in ways never imagined.

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