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Trainee Insurance Jobs in Chicago, IL (NOW HIRING)

Medical Insurance and Dental Plans * On-the-job training * Advancement Opportunities * Promote-From-Within Culture Start Building your Career with Menards Today! Are you looking to start an exciting ...

Medical Insurance and Dental Plans * On-the-job training * Advancement Opportunities * Promote-From-Within Culture Start Building your Career with Menards Today! Are you looking to start an exciting ...

Medical Insurance and Dental Plans * On-the-job training * Advancement Opportunities * Promote-From-Within Culture Start Building your Career with Menards Today! Are you looking to start an exciting ...

Medical Insurance and Dental Plans * On-the-job training * Advancement Opportunities * Promote-From-Within Culture Start Building your Career with Menards Today! Are you looking to start an exciting ...

Medical Insurance and Dental Plans * On-the-job training * Advancement Opportunities * Promote-From-Within Culture Start Building your Career with Menards Today! Are you looking to start an exciting ...

Medical Insurance and Dental Plans * On-the-job training * Advancement Opportunities * Promote-From-Within Culture Start Building your Career with Menards Today! Are you looking to start an exciting ...

Medical Insurance and Dental Plans * On-the-job training * Advancement Opportunities * Promote-From-Within Culture Start Building your Career with Menards Today! Are you looking to start an exciting ...

Medical Insurance and Dental Plans * On-the-job training * Advancement Opportunities * Promote-From-Within Culture Start Building your Career with Menards Today! Are you looking to start an exciting ...

Medical Insurance and Dental Plans * On-the-job training * Advancement Opportunities * Promote-From-Within Culture Start Building your Career with Menards Today! Are you looking to start an exciting ...

Medical Insurance and Dental Plans * On-the-job training * Advancement Opportunities * Promote-From-Within Culture Start Building your Career with Menards Today! Are you looking to start an exciting ...

Medical Insurance and Dental Plans * On-the-job training * Advancement Opportunities * Promote-From-Within Culture Start Building your Career with Menards Today! Are you looking to start an exciting ...

Medical Insurance and Dental Plans * On-the-job training * Advancement Opportunities * Promote-From-Within Culture Start Building your Career with Menards Today! Are you looking to start an exciting ...

Medical Insurance and Dental Plans * On-the-job training * Advancement Opportunities * Promote-From-Within Culture Start Building your Career with Menards Today! Are you looking to start an exciting ...

Medical Insurance and Dental Plans * On-the-job training * Advancement Opportunities * Promote-From-Within Culture Start Building your Career with Menards Today! Are you looking to start an exciting ...

Medical Insurance and Dental Plans * On-the-job training * Advancement Opportunities * Promote-From-Within Culture Start Building your Career with Menards Today! Are you looking to start an exciting ...

Medical Insurance and Dental Plans * On-the-job training * Advancement Opportunities * Promote-From-Within Culture Start Building your Career with Menards Today! Are you looking to start an exciting ...

Medical Insurance and Dental Plans * On-the-job training * Advancement Opportunities * Promote-From-Within Culture Start Building your Career with Menards Today! Are you looking to start an exciting ...

Medical Insurance and Dental Plans * On-the-job training * Advancement Opportunities * Promote-From-Within Culture Start Building your Career with Menards Today! Are you looking to start an exciting ...

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Showing results 1-20

Trainee Insurance information

See Chicago, IL salary details

$26.3K

$44.8K

$65.4K

How much do trainee insurance jobs pay per year?

As of Jul 31, 2026, the average yearly pay for trainee insurance in Chicago, IL is $44,843.00, according to ZipRecruiter salary data. Most workers in this role earn between $34,000.00 and $52,500.00 per year, depending on experience, location, and employer.

What does a trainee insurance role involve?

A trainee insurance role typically involves learning the fundamentals of the insurance industry, including understanding different types of insurance policies, risk assessment, and customer service. Trainees often assist senior staff with policy administration, claims processing, and underwriting tasks. The position is designed to provide hands-on experience and training, allowing individuals to develop the skills needed for a successful career in insurance. Over time, trainees may have opportunities to specialize in areas like sales, claims, or underwriting, depending on their interests and company needs.

What are the key skills and qualifications needed to thrive as a Trainee Insurance professional, and why are they important?

To thrive as a Trainee Insurance professional, you need a basic understanding of insurance principles, analytical skills, and a relevant educational background such as a degree in finance, business, or economics. Familiarity with insurance software, CRM systems, and potentially industry certifications like CII (Chartered Insurance Institute) is advantageous. Strong communication, attention to detail, and a customer-focused mindset are standout soft skills in this role. These abilities are crucial for accurately assessing risk, building client trust, and ensuring efficient and compliant insurance operations.

What are some common challenges faced by trainee insurance professionals during their first year on the job?

Trainee insurance professionals often encounter challenges such as grasping complex policy details, adapting to regulatory requirements, and building effective communication skills with clients. Balancing administrative responsibilities with learning about different insurance products can also be demanding. However, with mentorship and on-the-job training, trainees gradually develop the confidence and expertise needed to succeed in the industry.

What is the difference between Trainee Insurance vs Insurance Agent?

AspectTrainee InsuranceInsurance Agent
Required CredentialsTypically no formal license, on-the-job trainingLicensed, often requires certification
Work EnvironmentTraining programs, supervised learningClient-facing, sales-focused
Employer & Industry UsageInsurance companies, training rolesInsurance agencies, sales roles

In summary, a Trainee Insurance is an entry-level position focused on learning and training within the insurance industry, often without requiring a license. An Insurance Agent, however, is a licensed professional responsible for selling insurance policies and advising clients. The trainee role is a stepping stone toward becoming a licensed insurance agent.

What are the most commonly searched types of Insurance jobs in Chicago, IL? The most popular types of Insurance jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Trainee Insurance jobs? Cities near Chicago, IL with the most Trainee Insurance job openings:
Infographic showing various Trainee Insurance job openings in Chicago, IL as of July 2026, with employment types broken down into 73% Full Time, and 27% Part Time. Highlights an 100% In-person job distribution, with an average salary of $44,843 per year, or $21.6 per hour.

Insurance Sales Trainee

Merrill Insurance Agency

Chicago, IL โ€ข On-site

$30K - $50K/yr

Part-time

Life, PTO

Re-posted 27 days ago


Job description

The Tremaine Merrill Farmers Insurance Agency is hiring driven Licensed Insurance Producers to join our growing team!

As a key member of our agency, youll work closely with clients to provide exceptional service, identify their insurance needs, and recommend tailored solutions. This is a rewarding opportunity to grow your career with competitive pay, advancement opportunities, and a supportive, dynamic environment.

If youre motivated, customer-focused, and ready to make a meaningful impact in the insurance industry, we encourage you to apply. Prior experience in insurance is preferred, and an active insurance license is required.

What are we looking for?

  • Passionate and Self-driven
  • Motivated
  • Competitive
  • Strong verbal and written communication skills
  • Adaptable

What do we provide our employees?

Competitive Pay: Base salary with unlimited income potential, commission, and bonuses for outstanding performance

Comprehensive Training: Gain hands-on experience and benefit from a supportive team environment

Career Growth: Opportunities to advance within the organization

Flexible Work Schedule: PTO, holidays off, and a flexible work environment

*Additional Perks: Youtube or Spotify Premium Subscription, professional development opportunities, and access to the latest technology tools


Benefits

Commission Only

Paid Time Off (PTO)

Work from Home

Flexible Schedule

Mon-Fri Schedule

Career Growth Opportunities

Evenings Off

Youtube or Spotify Premium Subscription


Responsibilities
  • Develop personalized insurance solutions for clients, including Auto, Home, Business, and Life insurance
  • Foster strong client relationships as a trusted advisor
  • Provide clients with risk assessments and advice tailored to their needs
  • Utilize technology and digital tools to streamline and enhance the client experience
  • Work toward milestone bonuses as you achieve agency goals and milestones
  • Collaborate with a dedicated team and engage in continuous learning opportunities

Frequently Asked Questions

1) What kind of training will I receive?

Our team provides training in sales techniques and product knowledge to set you up for success, along with ongoing mentorship.

2) Is this a commission-only role?

No, we offer a base salary plus uncapped commission potential and performance bonuses.

3) What can I expect to earn in my first year?

With a strong sales approach, you can expect to earn $70,000+ in your first year, combining your base salary, commissions, and bonuses.

4) Are there opportunities for businss ownership?

Absolutely! Our Protg Program is a professional development initiative designed to serve as a pathway to business ownership. It provides hands-on training, mentorship, and the tools you need to prepare for the opportunity to own your own agency.

5) What does the onboarding and training process look like?

Our onboarding process is designed to help you get up to speed quickly and confidently. It includes a comprehensive orientation, access to online training resources, and ongoing mentorship from the Agency Owner and District Office. Youll have all the support you need to succeed in your new role!

Why Tremaine Merrill Farmers Insurance Agency?

At the Merrill Insurance Agency, we believe in building lasting relationships with our clients while fostering a supportive and flexible work environment for our team. As a Sales Producer, youll be part of an agency that values innovation, collaboration, and work-life balance, empowering you to thrive professionally while enjoying the flexibility you deserve.

We pride ourselves on creating a positive and inclusive team culture where every individual has the opportunity to grow, succeed, and make a real impact. Youll have the freedom to tailor your work around your personal and professional goalsall while contributing to the growth and success of an agency that truly cares about its people and its clients.


Requirements
  • Illinois or bordering town resident
  • Sales experience or a client-facing background preferred
  • Proven trustworthiness, dependability, and commitment to ethical behavior
  • Strong verbal and written communication skills
  • Enthusiastic, coachable, and motivated to achieve goals
  • Clean Criminal Background Check
  • Previous Remote Experience
  • Active Property and Casualty Life. (Other licensing opportunites available after. Ie: Life/Health/Securities Licensing Assistance provided)