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Life Insurance Jobs in Chicago, IL (NOW HIRING)

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Life Insurance Agent

Elgin, IL · On-site

$10K - $25K/mo

Now Hiring -- Insurance Agents and Future Agents Ready to Build Something Real Whether you're already licensed or you've never sold a policy in your life, keep reading. At Bold Services, we teach ...

New

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Life Insurance Agent

Elgin, IL · On-site

$10K - $25K/mo

Now Hiring -- Insurance Agents and Future Agents Ready to Build Something Real Whether you're already licensed or you've never sold a policy in your life, keep reading. At Bold Services, we teach ...

New

Be Seen First

Life Insurance Agent

Elgin, IL · On-site

$10K - $25K/mo

Now Hiring -- Insurance Agents and Future Agents Ready to Build Something Real Whether you're already licensed or you've never sold a policy in your life, keep reading. At Bold Services, we teach ...

New

Life Insurance Agent

Chicago, IL · Remote

$50K - $100K/yr

This role does require a Life and Health Insurance License, but don't worry--we'll help you obtain it through a streamlined online course that takes just 7-10 days. Please note: Success in this role ...

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Life insurance license (or willingness to obtain one) * Self-motivated with a strong work ethic * Able to pass a background check * Professional working proficiency or fluency in both English and ...

Be Seen First

Life insurance license (or willingness to obtain one) * Self-motivated with a strong work ethic * Able to pass a background check * Professional working proficiency or fluency in both English and ...

Remote Life Insurance Agent

Joliet, IL · Remote

$69K - $150K/yr

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

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 ...

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 ...

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 ...

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 ...

Remote Life Insurance Agent

Gary, IN · Remote

$69K - $150K/yr

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

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 ...

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

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 ...

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Showing results 1-20

Life Insurance information

See Chicago, IL salary details

$31.4K

$90.8K

$135.6K

How much do life insurance jobs pay per year?

As of Aug 3, 2026, the average yearly pay for life insurance in Chicago, IL is $90,843.00, according to ZipRecruiter salary data. Most workers in this role earn between $74,700.00 and $103,100.00 per year, depending on experience, location, and employer.

What jobs pay 4000 a week without a degree?

High-paying jobs that can reach $4,000 a week without a degree often include roles such as insurance sales agents, real estate brokers, commercial pilots, or skilled trades like electricians and plumbers. These positions typically require specialized training, licensing, or experience rather than formal college degrees and may involve commission-based pay or overtime opportunities.

What are typical career advancement opportunities for someone starting in a life insurance sales role?

Professionals who start in life insurance sales often have multiple career paths available as they gain experience. Many advance to roles such as senior agents, team leaders, or sales managers, where they may oversee other agents or entire teams. Some professionals choose to specialize in areas like estate planning or become independent brokers, expanding the range of products and services they offer. Ongoing professional development, such as obtaining advanced certifications or designations, can also open doors to higher-level opportunities in insurance sales, management, or even regional leadership roles. Companies often provide training and mentorship programs to support this career growth.

What are the key skills and qualifications needed to thrive in the Life Insurance position, and why are they important?

To thrive in life insurance sales, you need a solid understanding of insurance products, financial services, and a relevant licensing certification such as a state-issued life insurance license. Familiarity with customer relationship management (CRM) software, quoting tools, and digital application systems is typically expected. Outstanding interpersonal communication, resilience, and consultative selling are important soft skills in this role. These competencies enable life insurance professionals to effectively build client relationships, navigate complex products, and achieve sales goals in a competitive market.

Is it hard to get a life insurance job?

Getting a life insurance job typically requires relevant sales or customer service experience, a license in insurance sales, and strong communication skills. Entry-level positions may be accessible with minimal experience, but higher roles often demand industry knowledge and certifications. The difficulty varies based on the job market and individual qualifications.

Is life insurance a good career?

Life insurance is a viable career option that involves selling policies and providing financial planning services. Success often depends on strong sales skills, industry knowledge, and obtaining relevant licenses such as the Series 6 or 63. It can offer flexible schedules and commission-based income, but requires persistence and client relationship management.

What is a Life Insurance job?

A Life Insurance job typically involves selling and managing life insurance policies to help clients secure financial protection for their families. Professionals in this field assess clients' needs, explain policy options, and guide them in selecting the right coverage. They may work as agents, brokers, or underwriters for insurance companies. Strong communication and sales skills are essential in this career.

Why do most insurance agents quit?

Most insurance agents quit due to the challenging nature of sales, high rejection rates, and the need for persistent prospecting. The job often involves commission-based pay, requiring strong communication skills and resilience, which can lead to burnout and high turnover.
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 cities near Chicago, IL are hiring for Life Insurance jobs? Cities near Chicago, IL with the most Life Insurance job openings:
Infographic showing various Life Insurance job openings in Chicago, IL as of July 2026, with employment types broken down into 1% As Needed, 73% Full Time, 21% Part Time, and 5% Contract. Highlights an 95% Physical, 2% Hybrid, and 3% Remote job distribution, with an average salary of $90,843 per year, or $43.7 per hour.

Life Insurance Agent

Family First Life Bold Company

Elgin, IL • On-site

$10K - $25K/mo

Full-time

This job post has expired today. Applications are no longer accepted.


Job description

Now Hiring — Insurance Agents and Future Agents Ready to Build Something Real

Whether you’re already licensed or you’ve never sold a policy in your life, keep reading. At Bold Services, we teach business owners how to build wealth with strategies most agents never learn, like the Executive Bonus Plan. And we teach our people how to actually deliver it.  If you’re licensed, great. We’ll hand you the training, the scripts, and the system to close at a higher level. If you’re not licensed yet, even better. We’ll help you get there and build you from the ground up, no bad habits to undo.  Here’s who we want. Hungry. Coachable. Someone tired of the nine-to-five grind who knows their why and is willing to work for it. You don’t need experience. You need drive.  What you get: real mentorship, a proven lead and content system, and a team building something bigger than a paycheck.  Apply now