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Captive Insurance Agent Jobs in Illinois (NOW HIRING)

Insurance Agent

IL · Remote

$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 ...

Manage licensed sales agent licensing and compliance across all active and expansion states ... Proven track record of success leading, scaling, and optimizing an in-house or captive insurance ...

Captive Insurance Agent information

See Illinois salary details

$24.2K

$63K

$117.7K

How much do captive insurance agent jobs pay per year?

As of Sep 3, 2026, the average yearly pay for captive insurance agent in Illinois is $63,008.00, according to ZipRecruiter salary data. Most workers in this role earn between $43,100.00 and $74,600.00 per year, depending on experience, location, and employer.

What is a captive insurance agent?

A Captive Insurance Agent is an insurance salesperson who works for a single insurance company, selling only that company's products. Unlike independent agents who represent multiple insurers, captive agents receive training, support, and leads from their parent company. They often benefit from exclusive products, company-backed marketing, and potential salary or commission structures. This role requires strong sales and customer service skills to help clients find policies that fit their needs while meeting company sales targets.

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

To thrive as a Captive Insurance Agent, you need in-depth knowledge of insurance products, strong sales acumen, and a valid state insurance license. Familiarity with CRM software, quoting platforms, and company-provided training programs is typical in this role. Outstanding customer service, persuasive communication, and resilience are crucial soft skills that enhance performance. These skills ensure agents efficiently match clients with appropriate products, meet sales targets, and foster long-term client relationships within a competitive industry.

What are the typical challenges faced by captive insurance agents, and how can they overcome them?

Captive Insurance Agents often face the challenge of meeting sales targets while offering only the products of one insurance company, which can limit options for certain clients. To overcome this, successful agents develop a deep understanding of their company's offerings and learn how to tailor solutions to a wide range of client needs. They often work closely with supportive teams, including sales managers and underwriters, to strategize on complex cases. Building lasting relationships through excellent customer service and ongoing professional development also helps agents stand out and achieve their goals.

Is it better to be a captive insurance agent?

Being a captive insurance agent means working exclusively for one insurance company, which can provide stability, training, and a clear product line. However, it may limit flexibility and earning potential compared to independent agents who can offer multiple carriers' policies. The choice depends on personal career goals and preferred work environment.

What are the most commonly searched types of Captive Insurance Agent jobs in Illinois?

The most popular types of Captive Insurance Agent jobs in Illinois are:

Infographic showing various Captive Insurance Agent job openings in Illinois as of August 2026, with employment types broken down into 1% As Needed, 70% Full Time, 24% Part Time, and 5% Contract. Highlights an 85% Physical, 1% Hybrid, and 14% Remote job distribution, with an average salary of $63,008 per year, or $30.3 per hour.

$60K - $150K/yr

Contractor

Re-posted 2 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.