Building Your Risk Financing Strategy with Captive Insurance

tiny businessperson standing in a large concrete maze in the middle of tall office buildings

Danielle Brown-Bourgeois , Courtney Hylant , Claire Richardson , Hylant Global Captive Solutions | August 11, 2026 |

tiny businessperson standing in a large concrete maze in the middle of tall office buildings

When considering starting a new captive or modifying an existing one, most organizations begin by asking questions such as "Should we have a captive?" It isn't whether your organization should have a captive. It's whether your overall risk financing strategy accurately reflects the way you do business right now and how you'll do it tomorrow. A captive might play an important role in that strategy, but it shouldn't be where you begin the conversation. Step one involves asking a more fundamental question: How should we finance risk to best support our long-term business objectives?

A strategic assessment is the first step in making those decisions. Typically, that assessment combines analysis of historical loss data, financial risk-bearing capacity, business objectives, existing insurance programs, and future operational plans to determine the most effective financing approach.

That involves asking targeted questions: What risks does your organization face today? Which risks are predictable enough to retain? Which are best transferred? How much volatility can your balance sheet comfortably absorb? What is your true economic cost of risk—not just insurance premiums, but retained losses, collateral requirements, capital commitments and financial uncertainty?

These questions establish the framework for every decision that follows, and the answers create real business value because they're driven by a thorough analysis instead of simple assumptions.

Organizations that already operate captives need to ask many of the same questions, although they may approach them from a different perspective. Has the captive kept pace with the business? Is it financing the right risks? Are there opportunities that didn't exist when the captive was first established? Has the company's appetite for retaining risk changed?

Captives often become part of the organization's infrastructure. Premiums are paid. Claims are handled. Board meetings occur. Everything functions as expected. Meanwhile, the business and its industry continue to evolve. Yet the captive often remains largely unchanged, renewing policies year after year, still structured around assumptions that may no longer reflect today's business.

One recent strategic assessment illustrates how easily companies can overlook potential opportunities. As they reviewed a client's existing captive, our consulting team began asking questions about the organization's employee benefits program.

The client's immediate response was "Why are you asking about that?" This revealed how narrowly the organization viewed its captive. It had never considered that the captive could support employee benefits as part of a broader financing strategy. We often see human resources handling employee benefits, which can be a great fit in the captive. However, if departments don't regularly communicate on insurance, this opportunity can be overlooked. These lines of coverage are often high-frequency, low-severity claims and help diversify the risk in the captive.

Such responses aren't unusual. While it's true that a captive is an insurance company, viewing it that way limits its potential to support the company's strategic business objectives. When a captive is properly integrated into an organization's overall financing strategy, it becomes a much more versatile financial tool than many executives realize.

The same basic principle applies to how a captive's surplus is managed and used. All that accumulated capital is really valuable when it's being deployed intentionally and strategically. Your objective shouldn't be to accumulate surplus for its own sake. It should involve putting capital to work where it creates the greatest long-term value.

Depending upon the organization's objectives and leadership's comfort level, excess surplus might support expanding the captive into new lines of coverage, investing in loss prevention initiatives, enhancing claim management capabilities, or even making strategic loans to the parent organization to support initiatives for future growth.

Another common finding from our team's strategic assessments is that knowledge fades over time. People retire or take jobs elsewhere. Directors move off the board and are replaced by people who inherited a captive they weren't involved in creating and may not fully understand. That's why education is critical. Helping leadership reconnect the captive to the organization's broader financial strategy often accomplishes far more than simply recommending changes to coverage, capital, or governance.

An effective strategic assessment doesn't begin with a predetermined destination. When it's complete, the recommendation might be to establish a captive, expand one, or make changes to an existing captive. Sometimes, the recommendation is to leave the current structure largely unchanged because it already aligns well with the organization's objectives. Those are all different answers to the same business questions.

That's why organizations should reframe their questioning to be all-inclusive. They should begin by determining the risk financing strategy that best supports the business they're building. Once that strategy is clear, the role of a captive often becomes clear as well.

The above information does not constitute advice. Always contact your insurance broker or trusted advisor for insurance-related questions.

Danielle Brown-Bourgeois , Courtney Hylant , Claire Richardson , Hylant Global Captive Solutions | August 11, 2026