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Insurance Retention Agent Jobs in Chicago, IL (NOW HIRING)

SKY SERVICES LLC

Retention Agent

Schaumburg, IL

$17 - $20/hr

As a Retention Agent for Sky Auto Protection, you will: * Re-negotiate contracts in an effort to ... Health insurance * Paid time off * Vision insurance Experience level: * 1 year Shift: * 8 hour ...

HUB

Personal Lines Retention Agent

Des Plaines, IL · Remote

$25.64/hr

As a dynamic start-up backed by a leading global insurance brokerage, VIU by HUB blends cutting ... The Personal Lines Retention Agent provides a high level of service to our individual clients and ...

HUB

Team Lead

Des Plaines, IL · On-site

... insurance industry experience (Property & Casualty preferred) * 2+ years as a top-performing Retention agent or similar customer service role with demonstrated success achieving retention goals

Insure Online

Insurance Sales Agent

Chicago, IL · On-site

$40K - $60K/yr

Work expiration lists to ensure client retention and provide alternate quotes when increases ... The desire to become a top-notch Sales Agent! * Bi-lingual Spanish a plus! Insure Online p rovides ...

Insure Online

Insurance Sales Agent

Bedford Park, IL · On-site

$40K - $60K/yr

Work expiration lists to ensure client retention and provide alternate quotes when increases ... The desire to become a top-notch Sales Agent! * Bi-lingual Spanish a plus! Insure Online p rovides ...

Insure Online

Insurance Sales Agent

Bedford Park, IL

$40K - $60K/yr

Work expiration lists to ensure client retention and provide alternate quotes when increases ... The desire to become a top-notch Sales Agent! * Bi-lingual Spanish a plus! Insure Online p rovides ...

Promoted2

Remote Insurance Agent

Gary, IN · Remote

$60K - $110K/yr

Remote Insurance Sales Agent | $60k-$110k+ First Year | No Cold Calling Earn strong first-year ... Manage client pipeline using our CRM system * Follow up to ensure satisfaction and policy retention

Promoted2

Remote Insurance Agent

Chicago, IL · Remote

$60K - $110K/yr

Remote Insurance Sales Agent | $60k-$110k+ First Year | No Cold Calling Earn strong first-year ... Manage client pipeline using our CRM system * Follow up to ensure satisfaction and policy retention

Promoted2

Remote Insurance Agent

Chicago, IL · Remote

$60K - $110K/yr

Remote Insurance Sales Agent | $60k-$110k+ First Year | No Cold Calling Earn strong first-year ... Manage client pipeline using our CRM system * Follow up to ensure satisfaction and policy retention

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All JobsInsurance Retention Agent JobsInsurance Retention Agent Jobs in Chicago, IL

Insurance Retention Agent information

See Chicago, IL salary details

$25.8K

$67K

$125.2K

How much do insurance retention agent jobs pay per year?

As of Aug 2, 2026, the average yearly pay for insurance retention agent in Chicago, IL is $66,982.00, according to ZipRecruiter salary data. Most workers in this role earn between $45,800.00 and $79,300.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as an Insurance Retention Agent, and why are they important?

To thrive as an Insurance Retention Agent, you need strong knowledge of insurance products, policy terms, and customer account management, often supported by a high school diploma or relevant insurance certifications. Familiarity with CRM software, policy management systems, and call center platforms is typically required. Excellent communication, problem-solving, and negotiation skills help you build rapport and address client concerns effectively. These abilities are essential for maintaining customer satisfaction, reducing policy cancellations, and driving business growth.

What is the difference between Insurance Retention Agent vs Insurance Customer Service Representative?

AspectInsurance Retention AgentInsurance Customer Service Representative
CredentialsLicensing may be required; sales and retention trainingGenerally customer service training; licensing varies
Work EnvironmentCall centers, insurance offices, remoteCall centers, insurance offices, remote
Employer & Industry UsageInsurance companies, agenciesInsurance companies, agencies, brokers
Primary FocusRetaining existing clients, upselling policiesHandling inquiries, providing policy info, resolving issues

While both roles involve communication with clients, Insurance Retention Agents focus on maintaining client relationships and reducing policy cancellations, often involving sales skills. Insurance Customer Service Representatives primarily address client questions and support needs. The roles overlap in work environment and credentials but differ in primary responsibilities.

Why do most insurance agents quit?

Most insurance retention agents quit due to high rejection rates, pressure to meet sales targets, and job stress. The role often involves commission-based pay, which can lead to income instability and burnout over time.

What jobs pay 4000 a week without a degree?

An Insurance Retention Agent can potentially earn around $4,000 weekly through commissions and bonuses, especially with experience and high sales performance. Other high-paying roles without a degree include sales positions, real estate agents, and certain entrepreneurial ventures, often requiring strong communication skills and self-motivation. These jobs typically involve commission-based pay structures and may require licensing or certifications depending on the industry.

What are some common challenges Insurance Retention Agents face, and how can they overcome them?

Insurance Retention Agents often encounter challenges such as handling dissatisfied clients, addressing concerns about policy costs, and competing with offers from other companies. To overcome these challenges, agents should focus on building strong relationships with clients, actively listening to their needs, and demonstrating the unique value of their company's products. Additionally, staying well-versed in policy details and industry trends empowers agents to provide tailored solutions and improve retention rates.

What is the highest paying insurance agent job?

The highest paying insurance retention agents typically earn higher commissions and bonuses, especially those working in specialized or high-value markets such as commercial insurance or life insurance. Experienced agents with strong sales skills and industry certifications can also increase their earning potential significantly, often reaching six-figure incomes in top roles or agencies.

What are Insurance Retention Agents?

Insurance Retention Agents are professionals who work for insurance companies or agencies with the primary goal of retaining existing clients. They reach out to policyholders whose policies are up for renewal or at risk of cancellation, addressing concerns, answering questions, and offering solutions to keep their business. Their responsibilities often include explaining policy benefits, handling customer complaints, and sometimes negotiating discounts or policy adjustments. By maintaining strong client relationships, they help reduce customer churn and support the company’s long-term growth.

What does a insurance retention specialist do?

An insurance retention specialist is responsible for maintaining existing client accounts by addressing their concerns, providing policy information, and offering solutions to retain their business. They often use communication skills and customer relationship management (CRM) tools to improve customer satisfaction and reduce policy cancellations.
What are popular job titles related to Insurance Retention Agent jobs in Chicago, IL? For Insurance Retention Agent jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Insurance Retention Agent jobs in Chicago, IL look for? The top searched job categories for Insurance Retention Agent jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Insurance Retention Agent jobs? Cities near Chicago, IL with the most Insurance Retention Agent job openings:
Insurance Retention Agent jobs near you
Infographic showing various Insurance Retention Agent job openings in Chicago, IL as of July 2026, with employment types broken down into 1% Locum Tenens, 92% Full Time, 5% Part Time, and 2% Contract. Highlights an 91% Physical, 2% Hybrid, and 7% Remote job distribution, with an average salary of $66,982 per year, or $32.2 per hour.

Retention Agent

SKY SERVICES LLC

Schaumburg, IL

$17 - $20/hr

Full-time

Medical, Dental, Vision, PTO

Re-posted 3 days ago

Job description

Outside of a home, vehicles are the second biggest financial investment a person can make. Not only are the costs of vehicles going up, the cost of vehicle repairs are as well. The average car loan in the United States is now 72-months at a cost of $550 dollars per month. On top of that, consumers have to worry about unexpected car repairs, be it a $90 sensor of a $4,000 transmission.

Simply put: Owning a car can be expensive and stressful.

That’s where we come in!

Here at Sky Auto Protection – a leader in the vehicle service contract industry – we provide consumers with an easy and affordable solution to protect themselves against unexpected vehicle repairs. As a nationwide provider of certified vehicle service contracts (commonly referred to as extended warranties), we protect tens of thousands of consumers nationwide by covering the cost of parts, labor, taxes, rental, roadside services, and even hotel and food reimbursement in the worst case scenario of breaking down far from home.

We are currently looking for driven, dedicated individuals to join our Customer Service team. As a Retention Agent for Sky Auto Protection, you will:

  • Re-negotiate contracts in an effort to retain customer business
  • Manage customer accounts
  • Answer consumer questions about their policy, claims and/or billing
  • Work with cross functional team members including finance, billing, sales, and administrators
  • Always remain positive in the face of adversity

All of our Retentions Agents receive the following:

  • Hourly wage plus commission
  • Paid training
  • Paid vacation and sick leave

We would like applicants to be proficient in Microsoft Office (Word, Excel, PowerPoint) and Customer Relationship Management software, but is not necessary for employment consideration.

While we would prefer applicants with retention/customer service experience, it is not required as we are confident in our training program, regardless of work experience or background.

If you are reliable, dedicated, committed, willing to exceed expectations and eager to work, you would be a perfect member to our team!

Sky Auto Protection is an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status.

Job Type: Full-time

Pay: $17.00 - $20.00 per hour

Expected hours: 40 per week

Benefits:

  • Dental insurance
  • Health insurance
  • Paid time off
  • Vision insurance

Experience level:

  • 1 year

Shift:

  • 8 hour shift
  • Day shift
  • Evening shift

Weekly day range:

  • Monday to Friday
  • Weekends as needed

Work setting:

  • In-person

License/Certification:

  • Driver's License (Preferred)

Work Location: In person

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