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Insurance Training Jobs in Chicago, IL (NOW HIRING)

Freeway Insurance

Insurance Sales Manager

Chicago, IL

$17 - $19/hr

Comprehensive paid training and licensing with continuous on-going training and mentorship * Recognition culture * Comprehensive Benefits package including medical, dental, vision and life insurance

Freeway Insurance

Insurance Sales Manager

Chicago, IL

$17 - $19/hr

Comprehensive paid training and licensing with continuous on-going training and mentorship * Recognition culture * Comprehensive Benefits package including medical, dental, vision and life insurance

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All JobsInsurance Training JobsInsurance Training Jobs in Chicago, IL

Insurance Training information

See Chicago, IL salary details

$26.8K

$54.9K

$95.8K

How much do insurance training jobs pay per year?

As of Sep 15, 2026, the average yearly pay for insurance training in Chicago, IL is $54,919.00, according to ZipRecruiter salary data. Most workers in this role earn between $44,800.00 and $61,800.00 per year, depending on experience, location, and employer.

What is insurance training?

Insurance training refers to the education and development programs designed to teach individuals about insurance products, regulations, sales techniques, and industry best practices. It can be provided to new hires, experienced agents, or anyone looking to enter the insurance field. Training may cover topics such as underwriting, claims processing, customer service, compliance, and ethics to ensure professionals meet industry standards and legal requirements. Effective insurance training helps employees stay updated with changes in laws and products, improving service quality and compliance.

What are the key skills and qualifications needed to thrive in insurance training, and why are they important?

To thrive in Insurance Training, you need a solid understanding of insurance products, regulatory requirements, and adult learning principles, often supported by a background in insurance and relevant instructional certifications. Familiarity with Learning Management Systems (LMS), virtual training platforms, and assessment tools is typically required. Excellent communication, adaptability, and interpersonal skills help trainers effectively engage diverse learners and respond to evolving industry needs. These skills ensure that training is accurate, engaging, and compliant, which is crucial for developing knowledgeable insurance professionals and reducing risk.

What are some common challenges faced by professionals in insurance training, and how can they be effectively addressed?

Professionals in insurance training often face the challenge of keeping up with frequent regulatory changes and ensuring that all training materials remain compliant and up to date. Additionally, engaging a diverse workforce with varying levels of experience and learning styles requires a flexible and interactive approach. Effective strategies include regular collaboration with compliance teams, utilizing digital learning platforms for quick updates, and incorporating interactive elements such as case studies and role-playing to enhance engagement and retention.

What is the difference between Insurance Training vs Insurance Agent?

AspectInsurance TrainingInsurance Agent
Required CredentialsTypically involves courses, certifications, and licensing prepRequires licensing, state exams, and ongoing education
Work EnvironmentClassroom, online courses, or self-studyOffice, client meetings, fieldwork
Industry UsageUsed for career preparation and skill developmentActive sales, client servicing, policy management

Insurance Training focuses on education and certification preparation, while Insurance Agents actively sell policies and manage client accounts. Training provides the foundational knowledge needed to become licensed, whereas agents apply that knowledge in real-world sales and customer service roles.

What are the most commonly searched types of Insurance Training jobs in Chicago, IL?

The most popular types of Insurance Training jobs in Chicago, IL are:

Insurance Training jobs near you
Infographic showing various Insurance Training job openings in Chicago, IL as of September 2026, with employment types broken down into 50% Full Time, and 50% Part Time. Highlights an 93% In-person, and 7% Remote job distribution, with an average salary of $54,919 per year, or $26.4 per hour.

Insurance Sales Manager

Chicago, IL

Freeway Insurance
See more jobs at Freeway Insuranceexternal

$17 - $19/hr

Full-time

Medical, Dental, Vision, Life, Retirement

Re-posted 16 days ago

Freeway Insurance rating

8.2

Company rating: 8.2 out of 10

Based on 12 frontline employees who took The Breakroom Quiz

Job description

Sign-On Bonus Opportunity of up to $1,000*

Pay Range:

$17 - $19 / hour

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: We reimburse up to $15 a month to an employee for their gym
  • 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:

The Store Manager is the driving force behind our business. This exciting position will challenge your sales abilities and give you the opportunity to gain substantial financial rewards, along with mentoring others to achieve the same. We are hiring talented leaders committed to their own success.

  • Lead the sales team’s daily performance and/or targets
  • Expand business by proactively building relationships with existing customers to meet the agreed upon production and active customer goals
  • Coach members of the sales team to deliver a standard of customer care consistently
  • Oversee the sales team to achieve operational targets and monitoring performance
  • Assists with any escalated customer service issues and/or questions that may arise
  • Executes all aspects of Store Operational Excellence (SOE)

The Perfect Match:

  • Personal Lines or Property and Casualty license preferred (but not required)
  • Bilingual in English and Spanish preferred
  • 2 or 4 year college degree or equivalent of experience/education
  • Previous experience leading, coaching, and mentoring sales teams
  • Understanding of fiduciary duty and maintaining high levels of integrity and ethics
  • Ability to build relationships with sales customers
  • 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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Benefits

Hours and flexibility

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