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Insurance Agent Trainer Jobs in Chicago, IL (NOW HIRING)

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

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 ...

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 ...

NACBA

Insurance Agent - South Holland, IL

South Holland, IL · On-site

$80 - $100/hr

Training and support from a local team from marketing, prospecting, business consultation and more ... Agent Incentive Program Requirements * Obtain Property and Casualty and Life and Health insurance ...

New

StaffMyAgency LLC

Insurance Agent

Mundelein, IL · On-site

$40K - $70K/yr

... insurance business from the inside out while working directly with a successful mentor agent ... You'll gain hands-on experience, extensive training, and the support needed to grow your own book ...

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Showing results 21-40

All JobsInsurance Agent Trainer JobsInsurance Agent Trainer Jobs in Chicago, IL

Insurance Agent Trainer information

See Chicago, IL salary details

$12

$27

$61

How much do insurance agent trainer jobs pay per hour?

As of Sep 8, 2026, the average hourly pay for insurance agent trainer in Chicago, IL is $27.31, according to ZipRecruiter salary data. Most workers in this role earn between $20.82 and $31.44 per hour, depending on experience, location, and employer.

What does an insurance agent trainer do?

An Insurance Agent Trainer is responsible for educating new and existing insurance agents on industry regulations, company policies, sales techniques, and product knowledge. They develop training materials, conduct workshops, and provide ongoing support to help agents improve their skills and meet performance goals. The trainer often evaluates agents' progress and adapts training programs to address specific needs. Their ultimate goal is to ensure that agents are well-prepared to represent the company and effectively serve clients.

What are the key skills and qualifications needed to thrive as an insurance agent trainer?

To thrive as an Insurance Agent Trainer, you need in-depth knowledge of insurance products, strong instructional skills, and experience in sales or agent roles, often supported by relevant insurance licenses. Familiarity with learning management systems (LMS), presentation software, and certification in training or adult education is frequently required. Exceptional communication, patience, and motivational skills help trainers effectively coach and inspire agents. These abilities are vital for ensuring agents are well-prepared, compliant, and confident in delivering high-quality service to clients.

What are some common challenges faced by insurance agent trainers when onboarding new agents, and how can they be addressed?

Insurance Agent Trainers often encounter challenges such as varying levels of industry experience among new hires, adapting training methods to different learning styles, and ensuring regulatory compliance is clearly understood. To address these, trainers typically use a mix of interactive workshops, role-playing scenarios, and ongoing assessments to reinforce key concepts. Open communication and regular feedback sessions also help trainers identify areas where agents need additional support, ensuring a smoother transition into their roles.

What is the difference between Insurance Agent Trainer vs Insurance Sales Manager?

AspectInsurance Agent TrainerInsurance Sales Manager
Required CredentialsLicenses for insurance sales, training experienceLicenses, management experience, sales background
Work EnvironmentTraining sessions, workshops, one-on-one coachingOverseeing sales teams, strategic planning
Employer & Industry UsageInsurance companies, training firmsInsurance companies, agencies
Search & Comparison IntentFocus on training roles, certification, coachingFocus on leadership, sales performance, management

While both roles involve insurance sales and require licensing, an Insurance Agent Trainer primarily focuses on educating and coaching agents to improve their sales skills. An Insurance Sales Manager oversees sales teams, sets strategies, and manages performance. The roles differ in scope: training versus management, but both are vital in the insurance industry.

Do insurance agent trainers get paid during training?

Insurance agent trainers typically receive compensation during training periods, especially if they are employed by an agency or company that pays trainers as part of their employment. Training may be considered part of their job responsibilities, and pay can include salary, hourly wages, or stipends depending on the employer's policies.

Is it hard to make money as an insurance agent trainer?

Making money as an insurance agent trainer depends on experience, sales skills, and the ability to attract clients or trainees. Income can vary widely, with successful trainers earning commissions, bonuses, or salaries based on performance and the size of their training programs.

Why do so many insurance agent trainers quit?

Insurance agent trainers often quit due to high job stress, demanding schedules, and the pressure to meet sales targets. Additionally, the role requires strong communication skills and ongoing certification, which can be challenging to sustain over time.

What are popular job titles related to Insurance Agent Trainer jobs in Chicago, IL?

For Insurance Agent Trainer jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Insurance Agent Trainer jobs in Chicago, IL look for?

The top searched job categories for Insurance Agent Trainer jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Insurance Agent Trainer jobs?

Cities near Chicago, IL with the most Insurance Agent Trainer job openings:

Insurance Agent Trainer jobs near you
Infographic showing various Insurance Agent Trainer job openings in Chicago, IL as of July 2026, with employment types broken down into 1% Locum Tenens, 92% Full Time, 5% Part Time, and 2% Contract. Highlights an 91% Physical, 2% Hybrid, and 7% Remote job distribution, with an average salary of $56,813 per year, or $27.3 per hour.

Insurance Sales Agent

HealthMarkets, Inc.

Chicago, IL • On-site

Contractor

Re-posted 7 days ago

Job description

Insurance Sales Agent
Insurance Sales Agent
Location: Chicago, Illinois
Job Number HM2025-0523 Date posted 02/02/2025 Join Us
HealthMarkets Overview
If you're looking for an exciting opportunity where you can change people's lives and achieve financial success as an independent insurance agent, you've come to the right place. Becoming an independent insurance agent with HealthMarkets is an opportunity unlike any other. HealthMarkets offers agents the resources and support they need to grow their businesses and succeed in the industry, all while making a difference in people's lives.
And who are we? HealthMarkets is a technology-enabled health insurance agency delivering high-touch, customized health and supplemental insurance solutions to individuals, families and small businesses. Millions of Americans depend on us to help explore their coverage options - and we're looking for independent insurance agents like you to help us continue that mission.
So, whether you're an experienced insurance agent looking for your next opportunity or are just starting out and looking for an opportunity to demonstrate your talents, HealthMarkets is the career move that can help change your life.
Job description
Never worked in the health insurance industry before? It's no problem. If you've got an entrepreneurial spirit and drive and are ready to start your own business, we want you. At HealthMarkets, independent agents are given the opportunity to achieve financial success on their own time and schedule. Need to coach your child's soccer game? Or show up to a family event? You've got the time because you work for yourself.
Plus, the opportunities for growth are endless. We provide you with the support, training, and resources you need to succeed on your terms. Get started today and watch your career take off to new heights.
48640-HM-0523
Disclaimer: Licensed Insurance Agents with HealthMarkets Insurance Agency are self-employed acting as independent contractors and not as employees. HealthMarkets independent licensed insurance agents shall for all purposes be deemed to be independent contractors and shall have no authority to act or represent themselves as an employee or partner of HealthMarkets Insurance Agency. An Independent licensed insurance agent with HealthMarkets is a commission only opportunity. HealthMarkets Insurance Agency, Inc., is licensed as an insurance agency nationwide except in MA. Not all agents are licensed to sell all products. Service and product availability may vary by state. 51934-HM-0326

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