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Entry Level Captive Insurance Agent Jobs in Chicago, IL

Insurance Agent

IL · On-site +1

$60K - $150K/yr

... model and the career/captive model so that you can be in control of your practice with ... Compensation: $60,000.00 - $150,000.00 per year YOUR FUTURE as an Independent Insurance Agent ...

AMG (The Alliance) is a premier insurance marketing organization, dedicated to providing our ... If you are looking for an opportunity to build a business, and become a top sales agent, we are ...

Ocean Imports Agent

Elmhurst, IL · On-site

$50K - $55K/yr

... or Entry level candidates with a degree related to Supply Chain or International Business ... Dental insurance * Health insurance * Paid time off * Vision insurance Ability to commute/relocate:

Ocean Imports Agent

Elmhurst, IL · On-site

$50K - $55K/yr

... or Entry level candidates with a degree related to Supply Chain or International Business ... Dental insurance * Health insurance * Paid time off * Vision insurance Ability to commute/relocate:

Ocean Imports Agent

Elmhurst, IL · On-site

$50K - $55K/yr

... or Entry level candidates with a degree related to Supply Chain or International Business ... Dental insurance * Health insurance * Paid time off * Vision insurance Ability to commute/relocate:

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Showing results 1-20

Entry Level Captive Insurance Agent information

See Chicago, IL salary details

$25.8K

$67K

$125.2K

How much do entry level captive insurance agent jobs pay per year?

As of May 28, 2026, the average yearly pay for entry level captive insurance 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 is the difference between Entry Level Captive Insurance Agent vs Insurance Sales Representative?

AspectEntry Level Captive Insurance AgentInsurance Sales Representative
CredentialsLicensing required, often specific to captive insurerLicensing required, varies by state and product
Work EnvironmentAgency offices, captive insurer settingsIndependent or agency-based, various settings
Employer & IndustryCaptive insurance companies, insurance industryInsurance agencies, brokerages, insurance industry
Search & Comparison IntentUnderstanding roles within captive insuranceGeneral insurance sales roles, career options

While both roles involve selling insurance products, an Entry Level Captive Insurance Agent works specifically for a captive insurer, focusing on their exclusive products, whereas an Insurance Sales Representative may sell a variety of insurance policies across multiple companies. The former typically requires specific licensing and works within a captive environment, while the latter may have broader product options and work in diverse settings.

What are the most commonly searched types of Captive Insurance Agent jobs in Chicago, IL? The most popular types of Captive Insurance Agent jobs in Chicago, IL are:

$60K - $150K/yr

Full-time, Part-time

Posted 4 days ago


Job description

Red Oak Risk Management is looking for sales professionals in the insurance and financial industry that want to be fiercely independent, but not alone. We have built Red Oak with a focus on being agent-centric by combining the best of the independent model and the career/captive model so that you can be in control of your practice with infrastructure and systems that support you to achieve success. We believe this model is the best approach for you as the agent and, in turn, for the client. If you feel:
- You are not getting paid what you are worth
- You are not in control of your practice
- You are not getting enough support
- You are not providing enough solutions for your clients
Then apply for a position at Red Oak. We would be honored to have the conversation.
Qualifications:
- A life, OR health, OR property and casualty license with at least one year of experience. However, for the right candidate, we are open to applicants without a license.
- The belief that if you focus on doing what is in the best interest of your client, you will make great money.
- Great interpersonal skills and ability to build rapport with clients and the team.
- Do it first mindset.
- Person of integrity and honor.
- Type of person that would ask for forgiveness rather than permission.
Responsibilities:
- As an agent with Red Oak you are responsible to build your book of business. We have systems, training, vendors, mentorship, best practices, and more to support you in that endeavor, but it must be understood that the "buck" stops with you.
- Take the initiative to achieve your personal goals, which will also fulfill our company goals.
- Establish customer relationships and recommend products based on a customer-focused, needs-based review process.
- Use our technology platform to provide easy communication to customers as well as to complete back-office tasks.
Benefits:
- Flexible Schedule. We value results not, time.
- Independence. You have the autonomy to make decisions on your own.
- Ownership of your book of business day one (except on P&C, after training is done and with success that too is yours)
- Ability to work from home.
- High commissions and renewal structure. With transparency on the compensation structure.
- No monthly fees, or joining fees. We pay for your technologies, email, website, and other operating expenses.
Still need more reasons to apply?
- Path to management with a proven track record of success. We will even support you to create your own agency if that is what you want.
- Full technology suite such as CRMs, websites, email, calendar tool, webinar tool, raters, case design, illustration software, and more.
- Complete Red Oak business system & sales process
- Participation in a team that has a long-term vision and a track record of providing value to the industry.
If you believe that the Red Oak vision will help you achieve your goals within the industry, then apply. If you are content with where you are, then we wish you great success! We know that Red Oak won't be for everyone.
We believe that every agent that works with us can and should enjoy what they do. If not, then we are all doing something wrong.
Our success is measured not only by economic standards but by the trust and credibility we earn from our clients and agents.
It is with that in mind, that we are eager to connect with you and discuss the Red Oak value further.
Job Types: Full-time, Part-time, Contract
Pay: $60,000.00 - $150,000.00 per year, with uncapped potential and the ability to create residual income
This is a remote position.
Compensation: $60,000.00 - $150,000.00 per year
YOUR FUTURE as an Independent Insurance Agent Starts Here
If you're looking for a career that offers flexibility, job stability, competitive compensation, and more, then you've come to the right place! Working with an independent agency is a great career choice.
Independent insurance agents protect our customers by providing home, auto, business, life and health insurance policies to fit their individual needs. Independent agencies are not bound to offering products from only one insurance company. Instead, we can offer customers a choice of policies from a variety of insurance companies to provide the best protection at a competitive price.
The demand for insurance professionals is growing every day! Is this career right for you?
This agency is independently owned and operated. Your application will go directly to the agency, and all hiring decisions will be made by the management of this agency. All inquiries about employment at this agency should be made directly to the location, and not to Big I of Illinois Association.