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Insurance Agent In Training Jobs in Chicago, IL (NOW HIRING)

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Insurance Agent In Training information

See Chicago, IL salary details

$25.8K

$67K

$125.2K

How much do insurance agent in training jobs pay per year?

As of Jul 7, 2026, the average yearly pay for insurance agent in training 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 are some common challenges faced by Insurance Agents In Training, and how can they be overcome?

Insurance Agents In Training often face challenges such as building a client base from scratch, learning complex insurance products, and meeting sales targets within tight deadlines. Successfully overcoming these challenges typically involves proactive networking, seeking mentorship from experienced agents, and dedicating time to product training and professional development. Many agencies offer structured onboarding programs and regular team meetings to support new agents, helping them develop effective sales strategies and stay motivated as they grow their careers.

What are Insurance Agents In Training?

Insurance Agents In Training are individuals who are learning the skills and knowledge required to become licensed insurance agents. They typically work under the supervision of experienced agents or managers, assisting with tasks such as client communications, policy research, and sales processes. During this period, they study insurance products, regulations, and sales techniques, and may also prepare for licensing exams. The goal is to gain practical experience and meet all qualifications to become fully licensed insurance agents.

What is the difference between Insurance Agent In Training vs Insurance Agent?

AspectInsurance Agent In TrainingInsurance Agent
Required CredentialsLicensing exam, pre-licensing educationLicensing exam, ongoing continuing education
Work EnvironmentTraining period, supervised salesIndependent or team sales, client meetings
Job ResponsibilitiesLearning policies, shadowing agentsSelling policies, advising clients, managing accounts

The main difference is that an Insurance Agent In Training is in a learning phase, focusing on gaining licensing and experience under supervision, while an Insurance Agent is fully licensed and actively selling insurance policies to clients.

What are the key skills and qualifications needed to thrive as an Insurance Agent In Training, and why are they important?

To thrive as an Insurance Agent In Training, you need foundational knowledge of insurance products, strong sales acumen, and typically a high school diploma or equivalent, with progress toward state insurance licensure. Familiarity with customer relationship management (CRM) systems, quoting software, and digital communication tools is essential. Outstanding interpersonal skills, resilience, and persuasive communication set top candidates apart in this role. These competencies ensure effective client engagement, regulatory compliance, and the ability to build a successful insurance portfolio.
What cities near Chicago, IL are hiring for Insurance Agent In Training jobs? Cities near Chicago, IL with the most Insurance Agent In Training job openings:
Insurance Agent In Training jobs near you
Infographic showing various Insurance Agent In Training job openings in Chicago, IL as of July 2026, with employment types broken down into 91% Full Time, 7% Part Time, and 2% Contract. Highlights an 91% Physical, 1% Hybrid, and 8% Remote job distribution, with an average salary of $66,982 per year, or $32.2 per hour.
Insurance Sales Agent - Customer Service

Insurance Sales Agent - Customer Service

Freeway Insurance

Franklin Park, IL • On-site

Full-time

Medical, Dental, Vision, Life, Retirement

Posted 7 days ago

New

Freeway Insurance rating

8.0

Company rating: 8.0 out of 10

Based on 10 frontline employees who took The Breakroom Quiz

143rd of 277 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
  • Mental Health Benefit: 12 therapy sessions and 13 additional psychiatric sessions.
  • 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

Pay

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