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Senior Life Insurance Jobs in Chicago, IL (NOW HIRING)

West Monroe

Senior Consultant, Insurance

Chicago, IL · On-site

$133K - $157K/yr

West Monroe is seeking a Senior Consultant to join our Insurance practice in Chicago. Our growing ... Employees (and their families) are covered by medical, dental, vision, and basic life insurance.

Indeed

Senior Insurance Analyst

Chicago, IL · On-site

Reporting to the Senior Insurance Manager, you'll play a pivotal role in embedding practical ... Benefits - Health, Work/Life Harmony, & Wellbeing We care about what you care about. We have a ...

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All JobsLife Insurance JobsSenior Life Insurance JobsSenior Life Insurance Jobs in Chicago, IL

Senior Life Insurance information

See Chicago, IL salary details

$25.8K

$82.7K

$168.4K

How much do senior life insurance jobs pay per year?

As of Aug 26, 2026, the average yearly pay for senior life insurance in Chicago, IL is $82,707.00, according to ZipRecruiter salary data. Most workers in this role earn between $42,800.00 and $106,100.00 per year, depending on experience, location, and employer.

What is a senior life insurance agent?

A Senior Life Insurance agent is a licensed professional who specializes in helping seniors find suitable life insurance policies that meet their needs, such as final expense, whole life, or term life coverage. These agents assess clients' financial situations, explain policy options, and guide them through the application process to ensure they secure the right coverage. Senior Life Insurance agents often work with multiple insurance providers to offer tailored solutions and provide ongoing support throughout the life of the policy.

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

To thrive as a Senior Life Insurance Agent, you need in-depth knowledge of insurance products, industry regulations, and sales strategies, typically supported by a valid state insurance license. Familiarity with customer relationship management (CRM) software, electronic application systems, and underwriting processes is essential. Strong interpersonal skills, active listening, and trust-building abilities set top performers apart in this role. These skills are crucial for effectively advising clients, building lasting relationships, and achieving sales targets in a highly competitive market.

What are some common challenges faced by senior life insurance agents, and how can they overcome them?

Senior Life Insurance agents often face challenges such as building trust with clients, navigating complex product offerings, and staying current with industry regulations. Overcoming these requires strong interpersonal skills, continuous professional development, and a deep understanding of clients’ needs. Successful agents invest time in client education, use reliable CRM tools to manage relationships, and participate in ongoing training to stay updated on new products and compliance requirements. Collaboration with underwriters and support staff can also streamline the application process and improve client satisfaction.

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

AspectSenior Life InsuranceLife Insurance Agent
CredentialsMay require industry experience, licenses, and advanced certificationsRequires licensing, often with less experience needed
Work EnvironmentTypically employed by insurance companies or agencies, focusing on senior clientsIndependent or employed, selling policies to a broad client base
Industry UsageSpecializes in policies for seniors, retirement planningSells various life insurance products across demographics

Senior Life Insurance professionals focus on providing insurance solutions tailored for seniors, often working within insurance companies. In contrast, Life Insurance Agents sell a variety of policies to clients of all ages, working independently or for agencies. While both roles require licensing, Senior Life Insurance roles often demand more industry experience and specialized knowledge.

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 Senior Life Insurance jobs in Chicago, IL?

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

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

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

What cities near Chicago, IL are hiring for Senior Life Insurance jobs?

Cities near Chicago, IL with the most Senior Life Insurance job openings:

Senior Life Insurance jobs near you
Infographic showing various Senior Life Insurance job openings in Chicago, IL as of August 2026, with employment types broken down into 65% Full Time, 31% Part Time, and 4% Contract. Highlights an 92% In-person, 4% Hybrid, and 4% Remote job distribution, with an average salary of $82,707 per year, or $39.8 per hour.

IL-Woodridge Senior Insurance Agent & Leadership Opportunity Life, Health & Medicare | Independent A

Woodridge, IL • On-site

AMERICAN SENIOR BENEFITS LLC
See more jobs at AMERICAN SENIOR BENEFITS LLCexternal

$50K - $100K/yr

Full-time

Medical, Life, Retirement

Re-posted 18 days ago

Job description

At Chicago One Financial, powered by American Senior Benefits 

we help America’s seniors protect what matters most through trusted life insurance, health insurance, Medicare, and retirement solutions. As a nationally growing, independent insurance agency with 175+ locations nationwide, we empower our agents with access to toprated carriers, advanced training, and true income potential.

Our mission is simple: serve seniors with integrity while building longterm, rewarding insurance careers.

Why This Insurance Career Stands Out


Uncapped commissions + renewal (residual) income
Fasttrack leadership & agencybuilding opportunities
Comprehensive licensing, training & mentorship provided
Flexible schedule with field, hybrid, or local territory focus
Multiple Arated insurance carriers & Medicare products

This is ideal for licensed insurance agents, careerswitchers, or emerging leaders seeking longterm income, autonomy, and advancement.


What You’ll Do
  • Conduct client needs assessments and personalized insurance consultations
  • Educate clients on life insurance, health insurance, Medicare, and supplemental products
  • Present and enroll clients in the bestfit insurance solutions
  • Complete applications, underwriting, and policy processing with accuracy and integrity
  • Set up premium payment methods and provide ongoing client support
  • Assist clients through claims followups and policy reviews
  • Build and manage your own book of insurance business
  • Follow up with clients to ensure retention, satisfaction, and referrals
  • Train and support team members as you advance into sales leadership
Leadership & Growth Path

This role offers a clear path to management and agency ownership. Highperforming agents may:

  • Recruit and mentor new insurance agents
  • Lead local teams and territories
  • Advance into Regional or National Leadership roles
  • Earn override income and longterm residuals

Hear From The Team


What We Look For

Competitive, goaldriven mindset
Strong communication & relationshipbuilding skills
Ability to learn insurance products quickly
Professional integrity and clientfirst approach
Leadership experience (a plus, not required)
Ability to start within 6 weeks

Active Life & Health Insurance License preferred
Licensing support available for qualified candidates

*Compensation is highly customizable, and should be discussed directly with the onboarding manager. 


USD $50,000.00 - USD $100,000.00 /Yr.

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