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Insurance Training Jobs in Chicago, IL (NOW HIRING)

Aflac

Insurance Agent - Side-by-Side Training!

Joliet, IL · On-site

$63K - $75K/yr

Insurance Sales Agent -- Side-by-Side Training Aflac | Commission-Based | Flexible Schedule We're growing our team and hiring both new and licensed insurance agents. Whether you're starting your ...

NOVACARE SERVICES INC

RN

Hillside, IL · On-site

Health insurance * Training & development We are seeking an LPN/ RN to join our team! You will be responsible for delivering high quality care to assigned patients. ​Responsibilities: * Care for ...

NOVACARE SERVICES INC

RN

Hillside, IL · On-site

Health insurance * Training & development We are seeking an LPN/ RN to join our team! You will be responsible for delivering high quality care to assigned patients. Responsibilities: * Care for ill ...

Shelter Insurance

Insurance Agent

Crown Point, IN

Professional Sales Training * Subsidies & Office Staff Reimbursement, if applicable * Computer ... Take the first step towards operating your own Shelter Insurance Agency today! Applicants must be ...

Shelter Insurance

Insurance Agent

Crown Point, IN

Professional Sales Training * Subsidies & Office Staff Reimbursement, if applicable * Computer ... Take the first step towards operating your own Shelter Insurance Agency today! Applicants must be ...

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Showing results 21-40

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 14, 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 Agent - Side-by-Side Training!

Joliet, IL • On-site

Aflac
See more jobs at Aflacexternal

$63K - $75K/yr

Full-time, Part-time

Dental, Vision

Re-posted 16 days ago

Aflac rating

7.2

Company rating: 7.2 out of 10

Based on 37 frontline employees who took The Breakroom Quiz

Job description

Job Description:

Pay: $63,268.00 - $75,752.00 per year

Ready to create a life you love in 2026?

As an Aflac Agent, you'll experience the freedom and flexibility you've always dreamed of, while helping others protect their loved ones and finances through supplemental insurance. This is more than just a job; it's a lifestyle and a career!

Embrace the Freedom:

Insurance Sales Agent — Side-by-Side Training

Aflac | Commission-Based | Flexible Schedule

We're growing our team and hiring both new and licensed insurance agents. Whether you're starting your career or already have your license, we'll get you positioned to succeed.

What You'll Do

  • Meet with individuals and businesses to offer supplemental insurance products (accident, critical illness, disability, and more)

  • Build and manage your own client base

  • Provide ongoing service and support to policyholders

What We Offer

  • 100% commission — uncapped earning potential

  • Flexible schedule — control your own hours and territory

  • Full training provided, including licensing support and side-by-side field training for new agents

  • Aflac-specific product training for already-licensed agents

  • Mentorship and ongoing support from an experienced team

  • Clear path to leadership and advancement

Qualifications

  • No prior experience or license required — we'll help you get licensed

  • Candidates with an active insurance license are strongly encouraged to apply

  • Strong communication and people skills

  • Self-motivated with a desire to build your own business

  • Reliable transportation

Ideal For

  • Career changers looking for unlimited income potential

  • Licensed agents seeking better products, support, and payout

  • Motivated individuals who want to work independently with a team behind them

No experience? We'll train you from scratch with side-by-side field support. Already licensed? We'll get you selling fast. Are you ready to take control of your career and build a brighter future?
Apply now and become an Aflac Insurance Agent!

This is your chance to:

  • Ditch the 9-to-5 grind and work on your own terms.
  • Earn unlimited income and achieve financial freedom.
  • Make a difference in the lives of others.
  • Be your own boss and build a successful business.

This is your chance to start a new year, a new you, and a new career. Don't wait, apply today!

Job Types: Full-time, Part-time

Benefits:

  • Dental insurance
  • Disability insurance
  • Flexible schedule
  • Vision insurance

This is not a salaried position. Aflac sales agents earn commissions, bonuses, residual income, and stock. Aflac’s affiliation with the Value-Added Service providers is limited only to a marketing alliance, and Aflac and the Value-Added Service providers are not under any sort of mutual ownership, joint venture, or are otherwise related. Aflac makes no representations or warranties regarding the Value-Added Service providers and does not own or administer any of the products or services provided by the Value-Added Service providers. Each Value-Added Service provider offers its products and services subject to its own terms, limitations and exclusions. Services, Terms and conditions are subject to change and may be withdrawn at any time. The value-added services may not be available in all states, and benefits/services may vary by state. The content within is for recruiting purposes only. This information is not approved to distribute to prospective insureds, to prospective accounts, or to use as a solicitation. Aflac sales agents are independent agents and are not Aflac employees. Aflac’s family of insurers includes Aflac and/or Aflac New York, and/or Continental American Insurance Company and/or Continental American Life Insurance Company. Aflac WWHQ | 1932 Wynnton Road | Columbus, GA 31999. Continental American Insurance Company | Columbia, SC.

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