Take Control of Your Insurance with Captive Solutions

Move beyond traditional insurance limitations. Gain greater control over your coverage, costs, and risk management strategy.
Healthcare & Commercial Captives

Two Powerful Ways to Transform Your Insurance Strategy

Traditional insurance forces you to accept rising premiums with little transparency or control over your coverage. Winter-Dent's captive solutions put you in the driver's seat, allowing you to customize your insurance program while retaining profits from strong risk management.

Commercial Captive

Your safety record should work for you, not your carrier.

A captive structure allows you to benefit from proactive risk management, retain underwriting profits when claims are kept low, and gain greater control over long-term insurance costs.


✅ Premiums based on your actual claims history

✅ Financial rewards for strong safety programs

✅ Complete transparency in premium management

✅ Customized risk management assistance

✅ Reduced accident rates through safety focus

✅ Retain underwriting profits and investment income

Is This Right for You?

Typically best for businesses with $100,000+ annually on workers’ comp premiums with a combined workers' comp, auto, and general liability minimum of $250,000, and claims consistently below 50% of premiums paid.

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Healthcare Captive

Rising healthcare costs and lack of control plague traditional group health plans.

A healthcare captive offers a smarter alternative where your organization takes ownership of its healthcare spend.


✅ Access to established, turnkey coverage solutions

✅ Direct relationships with top-tier reinsurance carriers

✅ Wholesale pricing that reduces middleman expenses

✅ Dedicated program services and support team

✅ Customized risk management assistance

✅ Greater flexibility and transparency


Is This Right for You?

Best for organizations with 50+ eligible employees who are financially stable and committed to implementing wellness programs that improve employee health.

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Dive Deeper into Captive Solutions

Your Captive Insurance Learning Center

Everything You Need to Know About Captives

Everything You Need to Know About Captives

Discover the essentials of captive insurance. Learn what captives are, how they work, real-world advantages, eligibility requirements, and long-term financial benefits.

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Property & Casualty Captive eBook

Property & Casualty Captive eBook

Explore how a captive provides customized coverage without compromising on protection or cost. Learn how captives financially reward proactive companies.


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A Complete Guide to Captives Resource

A Complete Guide to Captives Resource

Get answers to your most important questions. This comprehensive resource covers different types of captives and detailed comparisons with traditional insurance.

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Workers' Comp Captive Playbook

Workers' Comp Captive Playbook

Navigate your complete transition from traditional workers' comp to captive membership—from evaluating fit to maximizing ROI with this step-by-step playbook series.

Read Series
Insights

Learn More About Captives

Take Our Quick Assessment

Am I a Candidate for a Captive?

Want to determine your company’s readiness for captive participation and discover what steps to take toward smarter risk financing? It takes less than 5 minutes!

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Ready to Explore a Captive for Your Business?

Our team can help you determine if a captive is the right fit and guide you through every step of the process. Start a conversation today to see how proactive risk management can pay off for your organization.

Email Us

info@winter-dent.com

Call Us

(573) 634-2122