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Entry Level Life Insurance Jobs in Chicago, IL (NOW HIRING)

Four Seasons Heating

Entry Level Technician

Chicago, IL · On-site

$40K - $75K/yr

Entry-Level HVAC Technician Paid Training • Clear Career Path • Hands-On Experience • Take ... Basic Life Insurance (free to employees) * Holiday Pay * Paid Time Off * 401k with Matching

GTS Transportation

Be Seen First

Driver Recruiter - Entry level

Burr Ridge, IL · On-site

$39K - $65K/yr

GTS Transportation is looking for a dynamic and energetic entry-level Driver Recruiter to join our ... Company-provided life insurance policy. * Wellness Perk: Company-paid Life Time Fitness discount ...

Aerotek

Entry Level Machine Operator

Buffalo Grove, IL · On-site

$18.50 - $20.45/hr

Entry Level Machine Operator- NO EXPERINCE REQUIRED Pay & Shift: 3rd shift: 6pm-6am rotating $19.50 ... Life Insurance (Voluntary Life & AD&D for the employee and dependents) * Short and long-term ...

New

Redwood Logistics

Entry Level Sales

Chicago, IL

$100/hr

Entry-Level Sales Reports To: Director of Training Location: Chicago, IL Environment: Onsite Status ... Short-term and long-term disability; life insurance policies subsidized by company * Additional ...

Redwood Logistics

Entry Level Sales

Chicago, IL

$100/hr

Entry-Level Sales Reports To: Director of Training Location: Chicago, IL Environment: Onsite Status ... Short-term and long-term disability; life insurance policies subsidized by company * Additional ...

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Showing results 41-60

All JobsLife Insurance JobsEntry Level Life Insurance JobsEntry Level Life Insurance Jobs in Chicago, IL

Entry Level Life Insurance information

See Chicago, IL salary details

$31.4K

$90.8K

$135.5K

How much do entry level life insurance jobs pay per year?

As of Aug 23, 2026, the average yearly pay for entry level life insurance in Chicago, IL is $90,771.00, according to ZipRecruiter salary data. Most workers in this role earn between $74,700.00 and $103,000.00 per year, depending on experience, location, and employer.

What is an entry level life insurance?

An Entry Level Life Insurance job typically involves helping clients understand and purchase life insurance policies. Responsibilities may include generating leads, explaining coverage options, and processing applications. Most positions require strong communication skills and a willingness to learn about insurance products. Some roles offer training and licensing support. This is a great starting point for a career in the insurance industry.

What does an entry level life insurance do?

A typical day for an Entry Level Life Insurance agent often involves reaching out to prospective clients, scheduling consultations, and meeting with individuals or families to assess their insurance needs. You’ll also spend time preparing quotes, completing applications, and following up on leads, either independently or as part of a team. Many agents participate in team meetings for training, role-playing sales scenarios, and staying updated on policy changes. The work environment is usually a mix of office-based tasks and fieldwork, offering variety and opportunities to develop valuable sales and customer service skills.

What are the key skills and qualifications needed to thrive in an entry level life insurance position?

To thrive as an Entry Level Life Insurance agent, you need strong interpersonal skills, basic knowledge of insurance products, and typically at least a high school diploma or equivalent. Familiarity with customer relationship management (CRM) software and the process for obtaining state life insurance licensing is also important. Outstanding communication, persistence, and the ability to build trust quickly are valuable soft skills for success in this field. These skills enable agents to effectively connect with clients, understand their needs, and provide the best insurance solutions in a competitive industry.

What are the most commonly searched types of Life Insurance jobs in Chicago, IL?

The most popular types of Life Insurance jobs in Chicago, IL are:

What are popular job titles related to Entry Level Life Insurance jobs in Chicago, IL?

For Entry Level Life Insurance jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Entry Level Life Insurance jobs in Chicago, IL look for?

The top searched job categories for Entry Level Life Insurance jobs in Chicago, IL are:

Entry Level Life Insurance jobs near you
Infographic showing various Entry Level Life Insurance job openings in Chicago, IL as of August 2026, with employment types broken down into 80% Full Time, and 20% Part Time. Highlights an 100% In-person job distribution, with an average salary of $90,771 per year, or $43.6 per hour.

Entry-Level Outside Sales Representative -- Teachers, Coaches & Educators Welcome

The Impact Insurance Agency

Dolton, IL • On-site

$65K - $85K/yr

Full-time

Medical, Life

Re-posted 2 days ago

Job description

Entry-Level Outside Sales Representative — Teachers, Coaches & Educators Welcome

 Company: Impact Insurance Agency
Pay: $65,000–$85,000 average first-year income | Commission + Optional 6-Week Base Draw
Schedule: Full-Time | Independent Contractor
Industry: Supplemental Insurance | B2B Outside Sales
Location: Local Territory | In-Person

A Career Path for People Who Naturally Support Others

Many educators and coaches reach a moment where they want to keep helping people grow — just in a new environment that offers flexibility, professional development, and long-term earning potential.

At Impact Insurance Agency, we partner with local businesses to provide supplemental insurance solutions that support employees and their families during life's unexpected moments. Teachers, mentors, and trainers often find this role to be a natural extension of what they already do best: building trust, encouraging others, and guiding meaningful conversations.

If you're someone who leads with empathy, enjoys connecting with people, and finds purpose in helping others succeed, this opportunity offers a rewarding next chapter.

The Opportunity

This entry-level outside sales role blends education, relationship-building, and ongoing client support. You'll meet face-to-face with business owners and employees, helping them understand benefit options in a way that feels clear, supportive, and approachable.

You don't need previous sales experience. Our structured training program is designed specifically for individuals transitioning from education, coaching, or other service-driven roles.

As an independent contractor, you'll manage your own local territory while working within a collaborative environment that provides mentorship, guidance, and consistency.

What You'll Do

  • Build genuine relationships with local business owners and their teams
     

  • Lead enrollment-style conversations that feel educational rather than sales-driven
     

  • Listen carefully and offer thoughtful, people-focused solutions
     

  • Support onboarding, follow-ups, and long-term client relationships
     

  • Manage appointments, scheduling, and territory activity
     

  • Participate in weekly collaboration, coaching, and professional development
     

Training & Support

  • Step-by-step onboarding designed for educators transitioning careers
     

  • Hands-on field mentorship and real-world learning
     

  • Health & Life licensing assistance and reimbursement
     

  • Coaching focused on communication, leadership, and relationship-based service
     

  • A collaborative culture built on encouragement, not pressure
     

Compensation & Structure

  • Commission-based income with performance bonuses
     

  • Average first-year income: $65,000–$85,000 (performance-based)
     

  • Optional 6-week base draw while building your client base
     

  • Flexible daytime schedule with autonomy over your territory
     

  • Advancement opportunities into mentoring, training, or leadership roles
     

Ideal Background

This opportunity may resonate with you if you:

  • Have experience as a teacher, coach, educator, trainer, or mentor
     

  • Enjoy helping people feel confident in their decisions
     

  • Communicate with warmth, patience, and professionalism
     

  • Thrive in relationship-driven environments
     

  • Value collaboration and meaningful impact in your work
     

  • Are willing to obtain a Health & Life Insurance license (support provided)
     

Why Impact Insurance Agency

Our culture is built around service, collaboration, and genuine encouragement. Many of our leaders started in entry-level roles and grew through mentorship, consistency, and a strong desire to help others succeed — both clients and teammates alike.

Apply Today

If you're ready to take the communication and leadership skills you've built in education and apply them in a people-focused professional career, we'd love to connect.

https://www.theimpactinsuranceagency.com/