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Director Captive Insurance Jobs (NOW HIRING)

Ryan Specialty

Associate Captive Executive

Chicago, IL · On-site

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 ...

Farnsworth Group

Finance Director

Normal, IL · On-site

$175K - $215K/yr

The Finance Director plays a critical role in mergers and acquisitions, capital planning, captive insurance modeling, real estate financial management, and enterprise-wide budgeting and forecasting.

Farnsworth Group

Finance Director

Peoria, IL · On-site

$175K - $215K/yr

The Finance Director plays a critical role in mergers and acquisitions, capital planning, captive insurance modeling, real estate financial management, and enterprise-wide budgeting and forecasting.

Farnsworth Group

Finance Director

Springfield, IL · On-site

The Finance Director plays a critical role in mergers and acquisitions, capital planning, captive insurance modeling, real estate financial management, and enterprise-wide budgeting and forecasting.

Farnsworth Group

Finance Director

Saint Louis, MO · On-site

$120 - $160/hr

The Finance Director plays a critical role in mergers and acquisitions, capital planning, captive insurance modeling, real estate financial management, and enterprise-wide budgeting and forecasting.

Farnsworth Group

Finance Director

Frisco, TX · On-site

The Finance Director plays a critical role in mergers and acquisitions, capital planning, captive insurance modeling, real estate financial management, and enterprise-wide budgeting and forecasting.

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All JobsFinance and Insurance JobsInsurance JobsInsurance Agency Manager JobsDirector Captive Insurance Jobs

Director Captive Insurance information

See salary details

$11K

$80.9K

$148.5K

How much do director captive insurance jobs pay per year?

As of Aug 21, 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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Director Captive Insurance jobs near you
Infographic showing various Director Captive Insurance job openings in the United States as of August 2026, with employment types broken down into 1% As Needed, 73% Full Time, 21% Part Time, and 5% Contract. Highlights an 89% Physical, 1% Hybrid, and 10% Remote job distribution, with an average salary of $80,864 per year, or $38.9 per hour.

Director Risk Management

Herschend Family Entertainment

Peachtree Corners, GA • On-site

Full-time

Posted 17 days ago

Job description

Herschend is the world's largest family-held themed attractions company, with a portfolio of over 40 family entertainment brands across North America, including destinations, resorts, theme parks, water parks, immersive experiences, and content enjoyed by audiences worldwide.
While each of our family brands offers something unique, all are united by a shared purpose: Bringing Families Closer Together by Creating Memories Worth Repeating®. Our 22,000 passionate hosts make this purpose possible through everyday acts of love and service-what we call Heartspitality®-the intersection of heart and hospitality.
As an equal-opportunity employer, we strive to provide environments where every host, guest, and partner feels welcome, valued, and loved. We firmly believe that words and actions matter, which is why all individuals are to be treated equally and with respect. For more information, visit www.Herschend.com.
Herschend is seeking a Director of Risk Management to lead and advance the company's enterprise insurance, captive strategy, and risk analytics. This is a hands-on leadership role in a lean, high-impact department, partnering closely with the Chief Financial Officer and external advisors to strengthen the company's insurance program and maximize long-term captive value.
The Director will own the enterprise insurance, and analytics function end-to-end, including captive strategy, actuarial interpretation, renewal oversight, executive reporting, and team development. The role includes leadership of three direct reports and meaningful exposure to senior executives.
The ideal candidate brings deep technical fluency in insurance, captives, and analytics, paired with the judgment, curiosity, and communication skills to translate complex risk concepts into clear business decisions.
About the Role
In this role, you will serve as the internal owner and primary point of coordination for Herschend's captive insurance strategy and enterprise insurance program. You will work closely with the Chief Financial Officer, Chief Legal Officer, captive manager, insurance broker, actuaries, and internal business partners to support strong governance, thoughtful risk financing, and data-driven decision-making.
Key Responsibilities
Enterprise Insurance Program
  • Partner actively with brokers on insurance renewals across all lines, owning execution.
  • Bring broader thinking, market awareness, and a willingness to challenge the status quo to renewal strategy - questioning what has always been done and exploring what could work better.
  • Manage broker, carrier, TPA, and actuary relationships at a senior level; serve as the point of accountability for program structure, coverage decisions, and risk transfer strategy - with close collaboration and support from the CFO.
  • Administer enterprise-wide TCOR budgeting and cost allocation across commercial and captive premiums.
  • Oversee actuarial workflows end-to-end: exposure submissions, claims data, report interpretation, and communicating results clearly to finance, leadership, and operating companies.
  • Serve as the internal owner and day-to-day liaison with the external captive manager.
  • With close collaboration and support from the CFO and external advisors, help define and evolve the strategic direction of the captive - including growth opportunities, new lines of coverage, and program enhancements that increase flexibility and value.

Claims Management
  • Manage third party claims administration relationship.
  • Lead and develop three direct reports who manage claims across the organization.
  • Responsible for claim outcomes across all product lines.

People Leadership & Team Development
  • Lead, mentor, and actively develop three direct reports with a genuine commitment to their growth - not just managing tasks, but developing capability and confidence over time.
  • Help your team think more broadly: challenge them to question assumptions, leverage technology, and bring fresh perspective to how things get done.
  • Balance delegation with accountability; create the conditions for your team to operate with increasing independence.
  • Foster a collaborative, intellectually curious team culture that reflects Herschend's values and Rooted in Innovation principles.

Senior Leadership Engagement
  • Translate complex insurance, captive, and actuarial concepts into clear, decision-ready language for executives and senior leadership.
  • Develop and deliver executive-level presentations for management meetings, board sessions, and senior leadership reviews.
  • Serve as a trusted resource and escalation point for time-sensitive risk issues, regulatory questions, and coverage decisions.
  • Grow into a strategic advisor role - this position has meaningful and growing exposure to the C-suite for those who earn it.

Required Qualifications
  • Demonstrated experience with sophisticated enterprise insurance programs, including direct captive insurance involvement - you understand how captives work, how they are governed, and how to make them more valuable over time.
  • Strong insurance analytics foundation: actuarial concepts, loss reserving, exposure analysis, data validation, and translating complex results into business decisions.
  • Track record of working effectively with brokers, actuaries, TPA's, carriers, captive managers, and regulators.
  • Proven ability to communicate complex insurance and risk concepts to non-technical audiences, including senior executives.
  • Bachelor's degree in Risk Management, Finance, Business, or a related field; advanced degree (MBA, CPCU, ARM,CRM) a plus.
  • Minimum 10+ years of progressive insurance, captive, or risk management experience.

Preferred Experience & Leadership Attributes
  • Experience supporting M&A due diligence or integration from a risk and insurance perspective.
  • You are genuinely curious - about technology, about better ways of doing things, about what you don't yet know.
  • You ask "why do we do it this way?" - and you follow through on the answer.
  • You are comfortable being accountable for things you didn't personally create, and making sound judgment calls with incomplete information.
  • You lead with precision and patience - accurate under pressure, steady in ambiguity.
  • You are a developer of people, not just a manager of tasks.
  • You thrive in a collaborative environment - working alongside a CFO and internal and external partners.

Ideal Candidate Profile
The successful candidate will be a technically strong, business-minded insurance and risk leader who is curious, precise, collaborative, and comfortable operating in a visible role with enterprise-wide impact.
Success in this role often comes from work that is preventative, interpretive, and built over time: strengthening coverage, improving governance, clarifying risk decisions, and helping the organization make better choices before issues arise.
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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