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

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 ...

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All JobsInsurance Agent In Training JobsInsurance Agent In Training Jobs in Chicago, IL

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

Insurance Sales Agent

HealthMarkets, Inc.

Schaumburg, IL

Contractor

Posted 5 days ago

Job description

HealthMarkets Overview

If youre looking for an exciting opportunity where you can change peoples lives and achieve financial success as an independent insurance agent, youve 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 peoples 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 were looking for independent insurance agents like you to help us continue that mission.

So, whether youre 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? Its no problem. If youve 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 childs soccer game? Or show up to a family event? Youve 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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