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How Do I Introduce Captives to a New Prospect?

April 13th, 2026

2 min read

By Warren Cleveland

Hero Image How do I introduce captives to a new prospect
How Do I Introduce Captives to a New Prospect?
2:38

I Have a Prospect That I Want to Introduce Captives To. How Do I Do It?

The good news is you don't need to walk in with a full presentation. You don't need to explain how captives work. You don't need loss runs or five years of documents. What you need is one good question and four numbers.

Here's the approach.

Start with the pricing calculator. Before you ask your prospect for anything formal, you just need to know what they're paying for workers' comp, general liability, and auto on an annual basis, and what their average losses have looked like over the last five years. That's it. That's a back-of-the-napkin conversation you can have in the first ten minutes of any meeting.

You're not asking for their carrier. You're not asking for their current agent's involvement. You're just asking a few questions that any business owner can answer off the top of their head.

Then you take those numbers, run them through the calculator, and show them what they would have kept had they been in a captive over the last five years. You're not presenting a proposal. You're not explaining risk transfer, fronting carriers or fund structures. You're just circling a number on a page and saying, based on what you told me, this strategy could have saved you $800,000. Are you interested in learning more?

That's the whole first conversation. And here's why it works. Most business owners don't think about insurance as anything other than an expense. They write the check and move on. When you show them a number that represents what they left on the table, you reframe the entire conversation. Insurance stops being a cost and starts being something they could have controlled. That's when they lean in.

From there, if they want to understand more, you walk them through a short 101. How a captive works, what's good about it, what's not for everybody. Come at it with both sides, not a pitch. Let them decide if they want to go further. If they do, that's when you ask for the documents. And at that point, they're motivated to get them because now they understand what's at stake.

Don't lead with the mechanics. Lead with the money and the problem you're solving. The mechanics can come later. First, you need them to care.

We have the resources to back you up at every step of this. The calculator. The Captive 101 guide. The email you can send before you even have the first meeting. You don't have to figure out how to say this on your own.

We'll help you with everything else.

It's always your client. Never ours.

Warren Cleveland

Warren Cleveland launched Captive Coalition after firsthand experience as an independent agency owner revealed a major gap in the market: agents lacked access to the knowledge and resources needed to compete with large brokerages offering captive insurance solutions. Warren brings over a decade of insurance leadership—including as President of ReNu Insurance Group—and a career that spans aviation, real estate, and commercial insurance. His mission is to ensure agents stay in control, keep their best clients, and confidently lead with captives. Warren Cleveland, ACI, CIC, AAI