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Director Captive Insurance Jobs (NOW HIRING)

If you have a solid foundation in commercial insurance, thrive on ownership rather than oversight ... give directors a clear, confident view of program performance. * Engage directly with clients ...

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Director Captive Insurance information

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$11K

$80.9K

$148.5K

How much do director captive insurance jobs pay per year?

As of Sep 13, 2026, the average yearly pay for director captive insurance in the United States is $80,864.00, according to ZipRecruiter salary data. Most workers in this role earn between $60,000.00 and $93,000.00 per year, depending on experience, location, and employer.

What are the roles and responsibilities of a director captive insurance?

A Director of Captive Insurance oversees the management and operation of a captive insurance company, which is an insurance company established by a parent firm to insure its own risks. Their responsibilities include regulatory compliance, financial oversight, risk assessment, and ensuring the efficient administration of the captive. They also interact with regulators, auditors, and company leadership to ensure the captive meets its intended goals and adheres to legal requirements. Additionally, they may help design insurance programs and analyze loss trends to optimize risk management strategies.

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

To thrive as a Director of Captive Insurance, you need expertise in risk management, insurance regulations, and financial analysis, often backed by a bachelor's degree in finance, business, or a related field. Familiarity with insurance management systems, captive insurance software, and relevant certifications like ARM (Associate in Risk Management) or CPCU (Chartered Property Casualty Underwriter) is highly valued. Strong leadership, strategic thinking, and effective communication skills are essential for managing teams and collaborating with stakeholders. These skills are critical for effectively overseeing captive operations, ensuring regulatory compliance, and optimizing risk financing strategies.

What are the primary challenges faced by a director captive insurance when managing compliance across multiple jurisdictions?

A Director of Captive Insurance often faces the challenge of navigating complex and constantly evolving regulatory requirements that differ across jurisdictions. Staying compliant involves regularly monitoring changes in laws, maintaining thorough documentation, and coordinating with legal and compliance teams to ensure all filings and reporting deadlines are met. This role requires strong attention to detail, proactive communication with regulators, and the ability to adapt quickly to new compliance landscapes. Collaborating with external advisors and leveraging technology can help streamline these processes and mitigate risks.

What is the difference between Director Captive Insurance vs Underwriting Manager?

AspectDirector Captive InsuranceUnderwriting Manager
CredentialsInsurance licenses, industry certificationsInsurance licenses, underwriting certifications
Work EnvironmentCorporate, captive insurance companiesInsurance companies, brokerage firms
Employer & Industry UsageCaptive insurance providers, risk management firmsInsurance carriers, brokerage firms

The main difference is that a Director Captive Insurance oversees the management of captive insurance entities, focusing on risk retention strategies, while an Underwriting Manager handles the assessment and pricing of insurance policies within traditional insurance companies. Both roles require industry licenses and work within the insurance sector, but their focus areas and responsibilities differ significantly.

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

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Infographic showing various Director Captive Insurance job openings in the United States as of September 2026, with employment types broken down into 1% As Needed, 76% Full Time, 18% Part Time, and 5% Contract. Highlights an 84% Physical, 1% Hybrid, and 15% Remote job distribution, with an average salary of $80,864 per year, or $38.9 per hour.

Assistant Captive Director, Benefits

Rolling Meadows, IL • On-site

Arthur J. Gallagher & Co.
Insurance Services • 10K+ employees

Other

Posted 9 days ago


Arthur J. Gallagher & Co. rating

7.6

Company rating: 7.6 out of 10

Based on 93 frontline employees who took The Breakroom Quiz


Job description

Assistant Captive Director, Benefits

At Artex, we reimagine what risk management can be and we do it with bold thinking, deep expertise, and an unwavering belief in what's possible. As part of our global team, you'll help clients navigate complex risks through creative, forward-looking solutions that go beyond the expected. This is a place where innovation is encouraged, ideas are welcomed, and no two days look the same. We're a community of confidently curious problem-solvers, opportunity seizers, and collaborative thinkers, working together to challenge convention and shape the future of our industry. Here, you'll be supported to explore your potential, grow your expertise, and make a meaningful impact on a global scale.

Assistant Captive Director, Benefits reports to the Captive Director and is responsible for retaining, growing, and managing one or more Medical Stop Loss (MSL) Group Captives. The successful candidate will serve as a trusted advisor to captive members, clients, brokers, and service providers, helping drive the continued success and long-term growth of these complex risk financing programs. This is a highly visible role that combines client relationship management, strategic program oversight, and operational leadership. The individual will play a key role in guiding renewal strategy, supporting member engagement, analyzing program performance, and delivering exceptional service to captive participants. Working closely with internal stakeholders and external partners, this position offers the opportunity to influence business outcomes, solve complex challenges, and contribute to the growth of one of the industry's leading captive insurance organizations.

How you'll make an impact:

  • Manage the captive renewal process, including the collection, compilation, analysis, and presentation of updated client underwriting information.
  • Lead renewal discussions with insured members, clearly communicating rate changes, coverage modifications, and factors impacting premium increases or decreases.
  • Coordinate the planning, preparation, and delivery of materials for recurring captive member meetings.
  • Oversee the collection and distribution of loss summary reports to clients and captive service providers.
  • Provide responsive, high-quality service by addressing client inquiries and resolving issues in a timely manner.
  • Partner with the Captive Director to cultivate new business opportunities and follow up on prospect and referral activity from insureds and brokers.
  • Ensure all collateral requirements are met and educate members on annual collateral obligations and changes.
  • Maintain and monitor schedules related to premium payments, letters of credit, loss experience charges, and claims payments.
  • Manage policy issuance, endorsement activity, and premium audit processes to ensure accuracy and compliance.
  • Coordinate policy reviews and errors and omissions (E&O) assessments.
  • Oversee premium invoicing activities and monitor accounts receivable to support healthy cash flow management.
  • Review new business and renewal loss projections provided by carrier partners and identify key trends and exposures.
  • Analyze loss summaries for prospective business and provide initial recommendations and insights to the Captive Director.
  • Maintain and update medical stop-loss coverage templates to ensure consistency and accuracy across the captive program.
  • Foster strong, professional relationships with captive service providers, clients, brokers, and consultants.
  • Anticipate client and program needs, proactively identifying challenges and implementing effective solutions.
  • Ensure account management activities and systems adhere to corporate policies, procedures, and professional standards.
  • Provide leadership, direction, and performance oversight for the captive service consulting team.
  • Support strategic initiatives and special projects that contribute to the growth and success of the captive program.

About You:

  • Insurance qualification would be advantageous e.g. ARe or equivalent.
  • Minimum of five years post-qualifying experience within the re/insurance industry.
  • Minimum of five years of demonstrable team management experience.
  • Significant knowledge of the insurance marketplace and/or risk management regimes.
  • Advanced computer literacy skills, including Excel, Word and PowerPoint.
  • Demonstrable ability to manage teams, multi-task and adapt to changing priorities.
  • Highly motivated individual who is deadline driven and committed to delivering an excellent level of client service.
  • Excellent verbal, written, organizational skills with the ability to engage effectively at all levels.
  • Demonstrable career progression in previous roles.

Compensation and benefits at Gallagher are competitive and comprehensive, designed to support your well-being. Career development opportunities and ongoing learning are available, along with a collaborative, people-first culture with accessible leadership. The opportunity to do meaningful work with global reach and local impact is also provided.


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