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Captive Jobs in Chicago, IL (NOW HIRING)

Captive Resources

AVP/VP, Captive Executive

Itasca, IL

$110K - $150K/hr

The Assistant Vice President/Vice President, Captive Executive will execute business development strategies, initiate contact with existing and potential customers, identify their needs and sell and ...

Captive Resources

AVP/VP, Captive Executive

Itasca, IL · On-site

The Assistant Vice President/Vice President, Captive Executive will execute business development strategies, initiate contact with existing and potential customers, identify their needs and sell and ...

Ryan Specialty

Associate Captive Executive

Chicago, IL · On-site

Working alongside a Captive Executive, you'll manage day-to-day program operations, own key client and broker relationships, and help shape the strategic direction of the captives you're assigned to.

Ryan Specialty

Associate Captive Executive

Chicago, IL · On-site

Working alongside a Captive Executive, you'll manage day-to-day program operations, own key client and broker relationships, and help shape the strategic direction of the captives you're assigned to.

Captive Resources

Captive Support Manager

Itasca, IL · On-site

Lead a team of Captive Support professionals by driving operational excellence, developing employees, and ensuring consistent delivery of service, quality, and productivity goals. This role partners ...

Captive Resources

Captive Support Manager

Itasca, IL · On-site

$105K - $110K/hr

Lead a team of Captive Support professionals by driving operational excellence, developing employees, and ensuring consistent delivery of service, quality, and productivity goals. This role partners ...

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Captive information

See Chicago, IL salary details

$14

$22

$51

How much do captive jobs pay per hour?

As of Sep 1, 2026, the average hourly pay for captive in Chicago, IL is $22.52, according to ZipRecruiter salary data. Most workers in this role earn between $16.11 and $22.31 per hour, depending on experience, location, and employer.

What is a captive in the context of insurance?

Captives are specialized insurance companies that are created and wholly owned by one or more non-insurance companies to insure the risks of their owners. They allow organizations to manage risk more efficiently and potentially reduce insurance costs by retaining profits that would otherwise go to third-party insurers. Captives can provide coverage that may not be available or affordable in traditional insurance markets and offer more control over claims handling and risk management. They are subject to regulations and must be legally established according to the jurisdiction in which they operate.

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

To thrive as a Captive Insurance Manager, you need in-depth knowledge of insurance principles, risk management, and a relevant degree such as finance or accounting. Familiarity with captive management software, regulatory compliance tools, and industry certifications like ACI (Associate in Captive Insurance) are often required. Strong analytical thinking, attention to detail, and excellent client communication skills set top performers apart. These competencies are crucial for effectively managing captive insurance operations, ensuring compliance, and delivering value to clients.

What are common challenges faced by captive insurance managers in maintaining compliance and regulatory standards?

Captive managers often encounter challenges in navigating complex and evolving regulatory environments, as regulations can vary by jurisdiction and frequently change. Staying compliant requires ongoing education, meticulous record-keeping, and close collaboration with legal and financial teams. Additionally, managers must ensure timely and accurate reporting while balancing cost-effectiveness and risk management. Building strong relationships with regulators and leveraging compliance software can help reduce potential pitfalls and maintain the captive’s good standing.

What is the difference between Captive vs Insurance Agent?

AspectCaptiveInsurance Agent
CredentialsLicensed insurance agents, often with specific company trainingLicensed insurance agents, typically with broader industry certifications
Work EnvironmentWork primarily for one insurance companyWork independently or for multiple insurers
Employer & Industry UsageInsurance companies, captive agenciesIndependent agencies, brokerages
Search & Comparison IntentUnderstanding employment with specific insurersComparing career options in insurance sales

Captive insurance agents work exclusively for one insurance company, representing its products. Insurance agents may work independently or for multiple companies, offering a broader range of options. The key difference lies in employment structure and product representation, affecting career flexibility and product knowledge.

What are popular job titles related to Captive jobs in Chicago, IL?

For Captive jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Captive jobs in Chicago, IL look for?

The top searched job categories for Captive jobs in Chicago, IL are:

Captive jobs near you
Infographic showing various Captive job openings in Chicago, IL as of August 2026, with employment types broken down into 92% Full Time, 5% Part Time, and 3% Contract. Highlights an 69% Physical, 8% Hybrid, and 23% Remote job distribution, with an average salary of $46,850 per year, or $22.5 per hour.

AVP/VP, Captive Executive, Health Solutions

Itasca, IL • On-site

Captive Resources
Insurance Services • 51 - 200 employees
Learn more about Captive Resourcesexternal

Full-time

Medical

Re-posted 25 days ago

Job description

Consult with and advise group captive Board of Directors, execute business marketing strategies, support contact with existing and potential customers, identify their needs and manage ongoing services to meet those needs. Assist in developing and facilitating the captive proposal process for specific brokers/prospective captive members including pricing indication development and captive presentations. Create and build long term captive relationships. Requires extensive out of town travel, including proposal presentations, workshops, and board meetings.
ESSENTIAL EDUCATION AND EXPERIENCE: Bachelor's Degree in Business, Marketing/Sales, or other related discipline and at least five (5) years of experience in Health Insurance business development, underwriting or related. Experience with employee benefits and/or self-funded medical plans.
SKILLS/COMPETENCIES REQUIREMENTS:
  • Consult with Board of Directors on captive strategies, review and assess customer needs, and create customer relationships
  • Participate in Board of Directors meetings
  • Support efforts to manage and increase membership in assigned accounts
  • Support and maintain on-going broker, vendor, and captive relationships
  • Responsible for premium growth through existing renewals and assisting with new business development
  • Prepare analysis on captive data, strong communication skills required
  • Participate in on-site visits
  • Facilitate, create, and conduct PowerPoint presentations
  • Communicate price indications and captive proposals with team members and functional groups using standard models
  • Establish budgets
  • Responsible for directing contractual negotiations and assisting/participating in the negotiations as necessary
  • Responsible for professional looking documentation, including board books, proposals, and submissions
  • Communicate back to internal groups the outcome of the negotiations/proposals i.e. clear details, critical timeframes, and expectations
  • Oversee activities needed to support each assigned captive team
  • Actively participate in workshops and relationship building within assigned captive through interactions, structured activities, etc.

PRIORITIES: Captive Consulting, Membership Growth, Customer Service/Relationships
Equal Opportunity Employer
This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights notice from the Department of Labor.

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