Forming or joining a captive insurance program can affect millions of dollars in premiums, capital, collateral, claims, financing, and long-term operating obligations. It is not a decision that should begin with a tax projection or a sales presentation.
The Executive Captive Insurance Assessment is a free interactive tool designed for business owners, CEOs, CFOs, controllers, risk leaders, benefits professionals, counsel, and outside advisers evaluating whether captive insurance deserves formal analysis.
It does not simply ask whether a captive sounds attractive. It examines whether your organization has a defined insurance problem, credible risk and loss information, sufficient capital support, appropriate governance, and a legitimate insurance purpose. It then identifies the most reasonable next path—including when that path is not a captive.
The purpose of this tool is not to approve a captive. It is to help determine whether the organization’s facts justify the time and expense of a formal feasibility study—and which structure or alternative deserves closer examination.
Most captive insurance resources explain what a captive is. This assessment goes further by applying the major business, financial, insurance, and governance questions to your organization.
The assessment is designed to help answer questions such as:
After completing the assessment, you will receive a personalized preliminary executive memorandum. Depending on your answers, the tool may direct you toward:
Your memorandum will explain:
Plan on approximately 20–30 minutes. The assessment is intentionally detailed because a captive can represent a long-term, multi-million-dollar risk-financing decision.
No documents are required to begin.
Nothing is uploaded, and no contact information is required. You may optionally download a small answer file and restore it later when actual figures become available.
New to the subject? Read What Is Captive Insurance? A Business Owner’s Guide for a detailed explanation of captive mechanics, benefits, costs, capital, financing, tax concerns, and available structures.
A detailed preliminary assessment for owners, CFOs, risk leaders, counsel, and advisers evaluating whether captive insurance deserves formal feasibility analysis.
This is a detailed preliminary assessment for business owners, CFOs, risk leaders, counsel, and advisers evaluating a potentially multi-million-dollar risk-financing decision.
The reason the organization is exploring a captive affects both the economics and the level of tax and substance risk.
A captive is a long-term operating commitment. Financial stability and ownership horizon matter more than revenue alone.
Select the recurring risks that could potentially be retained, pooled, or financed through a captive. Specialized life-related arrangements are intentionally excluded from this general P&C and benefits screening.
Use incurred losses when available—not merely cash paid during the year. Select Actual, Estimate, or Unknown for each material figure.
A credible result depends on more than premium volume. The quality, development, and volatility of the loss data determine whether the risk can be modeled responsibly.
A captive should solve a defined risk-financing problem. It should not be selected merely because it exists.
A captive needs acceptable capital, collateral, and liquidity support—not merely enough cash to pay an annual premium. Some support may be financed, but financing adds its own fixed obligations and must survive an adverse claims year.
Outsourcing technical work does not eliminate the owner’s governance responsibility.
Preference cannot override economics, but it helps identify which structures deserve comparison.
These questions do not determine tax treatment. They identify whether the project is being approached as a real insurance program or designed backward from a desired tax result.
This review shows the principal inputs used by the rule-based decision engine. You may save an answer file now and return later with actual figures.
The assessment does not issue a regulatory approval, actuarial opinion, tax opinion, or recommendation to form a captive. It identifies the next level of analysis that appears justified by the information entered.
A result suggesting that a group captive, protected cell, sponsored captive, or single-parent feasibility study deserves investigation means only that the organization appears to have enough economic and operational substance to examine that path more formally.
A result recommending commercial-program optimization, better data, or formal retention analysis is not a failed result. It may prevent the company from committing capital and professional fees to a structure that is premature, unnecessarily complex, or poorly matched to the underlying risk.
The tool does not assume that forming a captive is the correct answer. Commercial insurance changes, higher deductibles, formal self-insurance, group captives, sponsored facilities, protected cells, and standalone captives are evaluated as different paths.
Executives often know some figures precisely and others only approximately. The assessment uses estimates without pretending they are verified and adjusts the confidence of the result accordingly.
When a premium, loss, capital, collateral, or financing figure is estimated or unknown, the memorandum identifies it and explains where the actual figure is commonly found. You can then return and rerun the assessment with stronger information.
Capital support does not always have to come entirely from uncommitted cash. The assessment can consider external borrowing, letters of credit, funded trusts, surplus notes, and combinations of funding sources while also testing interest expense, guarantees, renewal risk, and adverse-year debt-service capacity.
The tool examines whether the project begins with a defined insurance problem, actuarially supported premiums, real claims administration, adequate capitalization, and independent professional review. Tax-first or fund-access motives trigger stronger warnings rather than an encouraging captive recommendation.
The final memorandum organizes the issues a captive manager, actuary, broker, attorney, CPA, claims administrator, lender, reinsurer, and investment adviser may need to address. That can make initial meetings more focused and reduce the risk of allowing one provider to define the entire project.
No email address, phone number, or company identity is required. The assessment is intended to help management think through the decision before choosing whether to involve outside professionals.
Would a Professional Review Help Clarify Your Result?
Use your memorandum as the starting point for a focused conversation about the insurance problem, possible structures, missing evidence, and whether further analysis is justified.
Discuss Your AssessmentNo. This is a preliminary educational assessment. A formal feasibility study requires detailed actuarial modeling, financial projections, structure and domicile analysis, professional cost estimates, legal and tax review, and consideration of regulatory requirements.
It will identify whether further captive analysis appears justified and which structure or non-captive alternative deserves closer review. It does not authorize formation or prove that a captive will improve the company’s economics.
No. Actual figures are preferable, but estimates and unknown answers are permitted. The result will identify the figures that should be verified and invite you to return with actual information.
Helpful information includes annual premium by coverage line, three to five years of paid and incurred loss history, current deductibles and self-insured retentions, large-loss information, exposure trends, available capital, collateral capacity, and any proposed financing terms.
Yes. The assessment considers several possible capital and collateral sources. It also examines whether financing costs, guarantees, lender terms, renewal risk, and an adverse claims year could place excessive strain on the operating business.
No. Historical premiums minus historical losses are not projected captive savings. Fronting, reinsurance, claims administration, operating expenses, capital costs, financing, loss development, taxes, and investment income must all be modeled before the economics can be evaluated responsibly.
The assessment can identify group captives, sponsored captives or protected cells, and single-parent captives as possible paths. It also considers commercial-program changes and formal risk-retention alternatives when a captive is not yet justified.
The tool is designed for business owners, CEOs, CFOs, controllers, risk and insurance leaders, benefits professionals, internal counsel, and outside legal, tax, accounting, insurance, or financial advisers. More than one decision-maker can complete it separately and compare results.
The assessment does not require contact information, and answers are processed locally in the browser. Users may optionally download an answer file for later restoration. Review the tool’s Terms of Use before beginning.
Rerun it after replacing material estimates with actual figures, obtaining complete loss runs, receiving lender or collateral terms, completing a commercial-market review, or experiencing a significant change in premiums, claims, ownership, capital, or business strategy.
