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Life Insurance Agent Trainee Jobs in Chicago, IL

HMG Careers

Remote Life Insurance Agent

East Chicago, IN · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

New

Chime Insurance Group

Insurance Agent

Frankfort, IL · Remote

As an Insurance Agent at Chime Insurance Group, you will play a crucial role in helping clients ... Requirements Sell Life, Health & Medicare coverage remotely with a growing independent agency. 1099 ...

HealthMarkets, Inc.

Insurance Agent

Waukegan, IL

... your life. If youre an insurance agent with 4-5 years of experience, we want you. As an independent contractor licensed insurance agent with HealthMarkets, youll be collaborating with one of the ...

HealthMarkets, Inc.

Insurance Agent

Aurora, IL

... your life. If youre an insurance agent with 4-5 years of experience, we want you. As an independent contractor licensed insurance agent with HealthMarkets, youll be collaborating with one of the ...

HealthMarkets, Inc.

Insurance Agent

Schaumburg, IL

... your life. If youre an insurance agent with 4-5 years of experience, we want you. As an independent contractor licensed insurance agent with HealthMarkets, youll be collaborating with one of the ...

HealthMarkets, Inc.

Insurance Agent

Elgin, IL · On-site

... your life. If youre an insurance agent with 4-5 years of experience, we want you. As an independent contractor licensed insurance agent with HealthMarkets, youll be collaborating with one of the ...

HealthMarkets, Inc.

Insurance Agent

Naperville, IL · On-site

... your life. If youre an insurance agent with 4-5 years of experience, we want you. As an independent contractor licensed insurance agent with HealthMarkets, youll be collaborating with one of the ...

HealthMarkets, Inc.

Insurance Agent

Joliet, IL · On-site

... your life. If youre an insurance agent with 4-5 years of experience, we want you. As an independent contractor licensed insurance agent with HealthMarkets, youll be collaborating with one of the ...

HealthMarkets, Inc.

Insurance Agent

Chicago, IL · On-site

... your life. If youre an insurance agent with 4-5 years of experience, we want you. As an independent contractor licensed insurance agent with HealthMarkets, youll be collaborating with one of the ...

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Showing results 21-40

All JobsLife Insurance Agent JobsLife Insurance Agent Trainee JobsLife Insurance Agent Trainee Jobs in Chicago, IL

Life Insurance Agent Trainee information

See Chicago, IL salary details

$21K

$70K

$150.9K

How much do life insurance agent trainee jobs pay per year?

As of Aug 11, 2026, the average yearly pay for life insurance agent trainee in Chicago, IL is $69,984.00, according to ZipRecruiter salary data. Most workers in this role earn between $35,924.00 and $92,377.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a life insurance agent trainee?

To thrive as a Life Insurance Agent Trainee, you need a strong understanding of insurance products, basic sales techniques, and often a high school diploma or equivalent, with state-specific licensing required. Familiarity with customer relationship management (CRM) systems, insurance quoting tools, and completion of pre-licensing courses or certifications are typical technical requirements. Exceptional interpersonal skills, active listening, and resilience help distinguish top performers in this role. These capabilities are crucial for building client trust, effectively educating customers, and consistently achieving sales targets in a competitive market.

What is the difference between Life Insurance Agent Trainee vs Insurance Agent?

AspectLife Insurance Agent TraineeInsurance Agent
CertificationsTypically requires licensing, training programsRequires licensing, experience often preferred
Work EnvironmentTraining period, supervised environmentIndependent or team-based sales environment
Job ResponsibilitiesLearning sales techniques, shadowing agentsSelling policies, client consultations
Career StageEntry-level, training phaseFull-fledged sales professional

In summary, a Life Insurance Agent Trainee is in the training phase, focusing on learning and obtaining necessary licenses, while an Insurance Agent is a fully licensed professional actively selling policies and managing client relationships.

Why do most life insurance agent trainees quit?

Many life insurance agent trainees quit due to the challenging nature of building a client base, inconsistent income, and the need for strong sales skills. The job often involves long hours, rejection, and the requirement to pass licensing exams, which can be discouraging for some trainees.

Is it hard to get hired as a life insurance agent trainee?

Getting hired as a life insurance agent trainee can vary depending on the employer and location, but generally requires passing a licensing exam and completing training programs. Strong communication skills and a willingness to learn are important, and some companies prefer candidates with sales or customer service experience. The process may involve background checks and obtaining necessary licenses before starting the role.

What are some common challenges faced by life insurance agent trainees during their first year, and how can they overcome them?

Life Insurance Agent Trainees often encounter challenges such as building a client base from scratch, handling client rejections, and mastering complex insurance products. To succeed, new agents should focus on developing strong networking skills, seeking mentorship from experienced colleagues, and dedicating time to ongoing product and sales training. Proactively reaching out to potential clients and consistently following up can help build confidence and establish trust. Staying organized and resilient is key, as the first year is often the most demanding but also lays the foundation for long-term success.

Can you work for yourself as a life insurance agent trainee?

A life insurance agent trainee typically works under the supervision of a licensed agent or agency and is not usually authorized to work independently until they obtain their license. Once licensed, agents can often work as independent agents or start their own agency, but during training, they generally operate within a structured environment. Licensing requirements and regulations vary by state or country, which influence whether they can work independently at any stage.

What is a life insurance agent trainee?

A Life Insurance Agent Trainee is an individual who is in the process of learning how to sell life insurance policies to clients, typically under the guidance of experienced agents or through a structured training program. Trainees study the basics of different life insurance products, develop customer service and sales skills, and prepare for licensing exams required by the state. This entry-level role is designed to provide foundational knowledge about the insurance industry and help trainees gain real-world experience before becoming fully licensed agents. Successful completion of the training program often leads to a permanent position as a licensed life insurance agent. The position is ideal for those interested in a career in financial services and helping individuals plan for their financial future.
What are the most commonly searched types of Life Insurance Agent jobs in Chicago, IL? The most popular types of Life Insurance Agent jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Life Insurance Agent Trainee jobs? Cities near Chicago, IL with the most Life Insurance Agent Trainee job openings:
Life Insurance Agent Trainee jobs near you

Mortgage Protection Life Insurance Agent

GIA Legacy Planning

Chicago, IL • On-site, Remote

$105K - $137K/yr

Full-time

Posted 6 days ago

Job description

Mortgage Protection Life Insurance Agent
Location: Remote Position/Work from Home
Job Type: Full-Time/Part-Time
Compensation: Commission-Based
About Us:
We are seeking motivated Mortgage Protection Insurance Agents who are ready to grow their careers with unlimited earning potential. Whether you're experienced or new to the industry, we provide the training, tools, and support you need to succeed.
As part of our team, you'll receive exclusive leads through our proprietary CRM, access to our Summit training system to help you get up to speed quickly, weekly training, social media guidance, and proven sales platforms to help you grow your business.
If you're driven, coachable, and ready to make a difference while building a rewarding career, we'd love to hear from you!
Responsibilities:
  • Identify client needs and recommend tailored insurance solutions
  • Develop and maintain strong client relationships
  • Generate leads through networking, referrals, and company-provided resources
  • Educate clients on available policies and coverage options
  • Follow up with prospects to close sales and maintain customer satisfaction
  • Stay informed about industry trends and product offerings
  • Work independently while collaborating with a supportive team

What We Offer:
  • Competitive commission structure with potential for bonuses
  • Flexible work schedule (remote position)
  • Comprehensive training and mentorship programs
  • Access to top-rated insurance carriers and products
  • Opportunities for career growth and leadership development
  • Supportive team culture with ongoing coaching and professional development

Requirements:
  • Insurance license (or willingness to obtain one - we provide guidance)
  • Strong communication and interpersonal skills
  • Self-motivated with a results-driven mindset
  • Ability to work independently and manage time effectively
  • Have own technical devices to conduct laptop, iPad, and a cell phone

Locations Chicago, IL Remote status Fully Remote

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