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Entry Level Insurance Agent Training Program Jobs in Chicago, IL

HealthMarkets, Inc.

Insurance Sales Agent

Waukegan, IL · On-site

Insurance Sales Agent Insurance Sales Agent Location: Waukegan, Illinois Job Number HM2025-0539 ... We provide you with the support, training, and resources you need to succeed on your terms. Get ...

HealthMarkets, Inc.

Insurance Sales Agent

Joliet, IL · On-site

Insurance Sales Agent Insurance Sales Agent Location: Joliet, Illinois Job Number HM2025-0527 Date ... We provide you with the support, training, and resources you need to succeed on your terms. Get ...

HealthMarkets, Inc.

Insurance Sales Agent

Chicago, IL · On-site

Insurance Sales Agent Insurance Sales Agent Location: Chicago, Illinois Job Number HM2025-0523 Date ... We provide you with the support, training, and resources you need to succeed on your terms. Get ...

HealthMarkets, Inc.

Insurance Sales Agent

Elgin, IL · On-site

Insurance Sales Agent Insurance Sales Agent Location: Elgin, Illinois Job Number HM2025-0525 Date ... We provide you with the support, training, and resources you need to succeed on your terms. Get ...

HealthMarkets, Inc.

Insurance Sales Agent

Aurora, 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.

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Showing results 21-40

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 Mentorship Program

Grayslake, IL • On-site

Farmers Insurance - District 2223
See more jobs at Farmers Insurance - District 2223external

$36K - $70K/yr

Full-time

Dental, Life, PTO

Re-posted 23 days ago

Job description

Are you a motivated, goal-driven individual with a passion for sales and helping others? Do you want a career that offers financial growth, personal development, and the potential to build something of your own with the guidance of industry leaders? If so, the Farmers Insurance Protg Program may be the perfect fit.

This program offers a unique opportunity to learn the insurance business from the inside out while working directly with a successful mentor agent. Youll gain hands-on experience, extensive training, and the support needed to grow your own book of business with the option to pursue long-term advancement and leadership.

Salary Range: $36,000.00 - $70,000.00 per year (includes Base + Commission + Bonus Opportunities)

Benefits

  • Career Growth Opportunities
  • Flexible Schedule
  • Life
  • Dental
  • Disability
  • Mon-Fri Schedule
  • Paid Training
  • Paid Time Off (PTO)
  • Opportunity to go hybrid once you hit goals!

Requirements

  • Possess a genuine willingness to learn, be intuitive and resourceful and be coachable.
  • Be a great self-starter with a sense of urgency.
  • Excellent Communication/interpersonal skills.
  • Career minded vision.
  • Be capable of handling customer rejection.
  • Previous work experience in sales, marketing, promotions or telemarketing.
  • Ability to adapt to change, learn new things quickly, and work in a fast-paced environment.
  • Property & Casualty and Life & Health license preferred, but willing to assist with this process for the right candidate.