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

PSI Groups

Life Health Insurance Agent

Chicago, IL · On-site

The life insurance industry is changing fast. Millions of families are still uninsured or ... Training is provided. Licensing support is available. If you are looking for more than another ...

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All JobsHealth Insurance Trainer JobsHealth Insurance Trainer Jobs in Chicago, IL

Health Insurance Trainer information

See Chicago, IL salary details

$11

$27

$49

How much do health insurance trainer jobs pay per hour?

As of Sep 3, 2026, the average hourly pay for health insurance trainer in Chicago, IL is $27.85, according to ZipRecruiter salary data. Most workers in this role earn between $19.57 and $32.21 per hour, depending on experience, location, and employer.

What is a health insurance trainer?

Health Insurance Trainers are professionals who provide education and training about health insurance products, policies, regulations, and procedures. They typically work for insurance companies, healthcare organizations, or training agencies, helping employees, agents, or clients understand health insurance plans, compliance requirements, and best practices. Their responsibilities may include developing training materials, conducting workshops or seminars, and staying updated on industry changes to ensure accurate information is delivered. Health Insurance Trainers play a crucial role in improving the knowledge and effectiveness of insurance staff and agents.

What are the key skills and qualifications needed to thrive as a health insurance trainer?

To thrive as a Health Insurance Trainer, you need in-depth knowledge of health insurance policies, training methodologies, and usually a background in healthcare or insurance administration. Familiarity with learning management systems (LMS), presentation software, and certifications such as Certified Professional in Learning and Performance (CPLP) are commonly required. Strong communication, adaptability, and interpersonal skills help trainers engage diverse learners and address complex topics effectively. These skills and qualifications ensure that training is accurate, compliant, and impactful, supporting organizational success and regulatory adherence.

What are some common challenges health insurance trainers face when delivering training to new hires?

One of the main challenges Health Insurance Trainers encounter is effectively communicating complex policy details and regulations to trainees with varying levels of experience. Trainers must break down technical concepts into understandable terms while ensuring compliance requirements are met. Additionally, adapting training methods to accommodate different learning styles and keeping sessions engaging can be demanding. Trainers often collaborate closely with HR and compliance teams to ensure training materials remain up-to-date with changing laws and company policies.

What is the difference between Health Insurance Trainer vs Health Insurance Agent?

AspectHealth Insurance TrainerHealth Insurance Agent
CertificationsTypically requires industry certifications and training credentialsRequires licensing and certification specific to insurance sales
Work EnvironmentPrimarily conducts training sessions, workshops, and seminarsWorks directly with clients, selling insurance policies
Employer & Industry UsageEmployed by insurance companies, training organizations, or as independent trainersEmployed by insurance agencies or as independent agents
Primary FocusEducating and training others about health insurance products and regulationsSelling health insurance policies and advising clients

While both roles involve health insurance knowledge, a Health Insurance Trainer focuses on educating others, whereas a Health Insurance Agent primarily sells policies. Understanding these differences helps job seekers identify the right career path in the health insurance industry.

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

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

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

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

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

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

Health Insurance Trainer jobs near you
Infographic showing various Health Insurance Trainer job openings in Chicago, IL as of August 2026, with employment types broken down into 73% Full Time, and 27% Part Time. Highlights an 90% In-person, and 10% Remote job distribution, with an average salary of $57,928 per year, or $27.9 per hour.

Life & Health Insurance Agent

TransGlobal Holdings Co.

Chicago, IL • Remote

Full-time, Contractor

Medical, Life, Retirement

Posted 6 days ago

Job description

We are seeking motivated and licensed Life & Health Insurance Agents who are interested in building their own client base, growing their sales business, and expanding their income opportunities through an All-in-One Financial Services platform.

What You’ll Do

  • Develop and manage your own client relationships and prospect for new business
  • Identify clients’ insurance, retirement, and financial needs
  • Present appropriate Life & Health insurance solutions
  • Build and maintain a long-term book of business
  • Participate in ongoing product and sales training
  • Collaborate with other professionals to help meet clients’ broader financial needs

What We’re Looking For

  • Active Life & Health Insurance License required
  • Previous sales experience preferred
  • Strong communication and relationship-building skills
  • Self-motivated and comfortable working independently
  • Strong interest in sales and business development
  • Willingness to learn and continuously develop
  • Entrepreneurial mindset and desire to build a long-term business

What We Provide

You build the client relationships. We provide the platform, resources, and opportunities to help you grow.

  • Remote work flexibility
  • Product and sales training
  • Illustration and case design support
  • Underwriting and application support
  • Professional collaboration and networking opportunities
  • Opportunities to earn additional compensation by referring clients to other qualified professionals and services within our network
  • Access to an All-in-One Financial Services platform, including:
    • Life & Health Insurance
    • P&C  
    • Medicare
    • Annuities & Retirement Planning
    • Investments
    • Tax Services
    • Real Estate
    • Private Lending

About Us

TransGlobal stands as one of the largest insurance general agencies in the US, boasting over 30 offices nationwide. We pride ourselves on delivering an all-in-one financial service platform covering insurance, real estate, lending, investment, retirement planning, and tax services. With a network of over 5000 licensed professionals, we represent top-rated insurance companies offering products tailored to diverse client needs. Visit our website: TransGlobalUS.com.

Compensation & Employment

  • Independent Contractor (1099)
  • Commission-based compensation
  • Additional compensation opportunities through qualifying referrals, subject to applicable laws, regulations, and program terms
  • Remote and flexible schedule
  • No guaranteed salary or employee benefits

This is an independent 1099 opportunity for licensed professionals who are motivated to build their own business and expand their income opportunities.