When it comes to retaining large, high-value clients in the middle market, captive insurance should be one of the first solutions every producer considers. Yet many agents avoid the topic entirely—often for reasons that have less to do with the client’s needs and more to do with the producer’s own hesitations.
The truth? Failing to offer captives could cost you a $300,000 revenue client overnight. And in today’s competitive market, someone else will step in and take that account if you don’t.
In this post, we’ll break down the three biggest mental roadblocks holding agents back from selling captives, show you how to address them, and explain how to position yourself as the quarterback of the client relationship—while increasing your value and your compensation.
This blog featured insights from Warren Cleveland from Captive Coalition.
Captive insurance is not a mysterious product reserved for the elite few—it’s a financial mechanism that allows companies to take more control over their insurance costs and claim outcomes.
From the outside, a captive looks almost identical to a traditional insurance program. The fronting carrier is still AM Best-rated, the policy and certificates look the same, and coverage remains compliant. The key difference lies in how the money flows internally.
Instead of sending every premium dollar into a traditional carrier’s pool—where it may never come back—clients in a captive structure retain a portion of their premium, earn investment income on reserves, and share in underwriting profits if losses are controlled.
For middle market clients with solid loss histories, this can mean substantial savings over time. And for producers, it’s a chance to deliver a measurable financial win while locking in the relationship long-term.
“Agents won’t sell what they don’t understand.” This is the first—and most common—reason producers avoid captives.
No one wants to look unprepared in front of a client. The fear is understandable: if you can’t confidently explain the mechanics of a captive, you risk damaging credibility. But not having the knowledge shouldn’t be the reason you lose a client.
The solution? Commit to learning the fundamentals. Break down the concept for yourself first, then for the client. For example:
Some captive managers treat the agent as a middleman and cut them out of the picture. This fear keeps many producers from bringing up the option at all.
But the right captive partner wants the agent to be the quarterback—the hero of the story—because it’s your relationship and your client.
By positioning yourself as the strategic advisor who brings the captive solution to the table, you strengthen your role in the account. You’re not giving up control—you’re taking more of it.
Many producers claim they “don’t have the time” to learn captives. In reality, it’s a prioritization problem.
If keeping a $300,000 revenue client is less important than a tee time, the issue isn’t the complexity of captives—it’s mindset. The “easy renewal” approach might work for a while, but eventually someone will come along who can have this conversation with your client.
A one-time investment in learning how captives work can create a lifetime return in client retention and growth.
One bonus roadblock is uncertainty about compensation. Many agents don’t know whether they’ll earn a commission, a service fee, or something else entirely.
The answer? Control the conversation by controlling your compensation model.
Example: If a $500,000 premium account pays you a $50,000 fee for your work, that fee stays the same even if you cut the client’s premium in half over three years. In fact, if you’ve saved them $250,000 annually, you can justifiably ask for more—because you’re delivering measurable, ongoing results.
If you’re calling on a CFO, you’re talking to someone who thinks strategically about finances. That makes them the ideal audience for the captive conversation.
Still, not every prospect is ready to jump straight into a captive. Loss-sensitive plans like incurred loss retros can be a great stepping stone.
These programs:
Once those controls are in place, moving to a captive becomes a natural next step.
One of the best ways to sell a captive—or any risk-financing alternative—is to teach clients how insurance companies make money.
When clients see the numbers, they understand why a captive could be a better long-term fit.
Selling captives isn’t just about knowing the product—it’s about mastering your craft. There are no shortcuts.
The top producers prepare like elite athletes. They study their playbook (risk management solutions), practice consistently (prospecting and sales skills), and execute with precision. Those who rely on the “easy button” approach eventually lose to someone willing to put in the work.
Captive insurance offers producers an opportunity to:
The only things standing in your way are mental roadblocks—lack of understanding, fear of losing control, and perceived complexity. Remove them, and you open the door to a stronger, more profitable future for both you and your clients.
If you’re ready to start the conversation about captives with your best prospects, make the time to learn the mechanics, partner with a manager who values your role, and position yourself as the problem solver—not just the policy seller.
Brian’s journey isn’t one of shortcuts or overnight success. It’s the story of a man who has faced battlefields, boardrooms, and hospital beds — and come out the other side with an unshakable sense of purpose. His agency is young, his vision is clear, and his “why” runs deep.
Artificial Intelligence is no longer a buzzword for tomorrow. It’s today’s most powerful tool for increasing efficiency, lowering costs, and growing your book of business faster than ever before. For insurance producers and agency owners, this isn’t a matter of curiosity or a “nice to have” anymore. It’s a necessity. The reality is that your competition may already be using AI-powered tools to identify prospects, streamline service, and close deals before you even realize you’re in the game.
In every season of The Protege, one thing becomes crystal clear—success in the commercial insurance industry isn’t about where you start, it’s about who you become.
In this episode of the Power Producers Podcast, I sat down with Lloyd Brown, a middle market producer from Orlando, Florida, whose story is equal parts faith, resilience, and purpose.
Salespeople are often taught to be charismatic, friendly, and well-liked. But as David Carothers and high-ticket sales expert Austin Medlin explore in their recent conversation, that mindset could be the very thing sabotaging your close rate. Austin, the founder of CloseSales.com, brings a fresh perspective from outside the insurance industry that perfectly aligns with what commercial producers face daily: buyers who need leadership, not another friend.
That idea sits at the heart of a powerful conversation I had with Joe Hollier, better known as Mr. Hotel, on the Power Producers Podcast. Joe’s story is one that every producer can learn from. He started his career in hospitality, spent two decades working in restaurants and hotels, and eventually found his way into insurance. What he brought with him from hospitality turned out to be his biggest competitive advantage — the ability to understand people.
In the fast-paced world of commercial insurance, new trends and technologies seem to emerge daily. But some strategies stand the test of time—particularly when they’re rooted in deep client empathy, practical experience, and a commitment to legacy. In this post, we reflect on insights shared by Kevin Ring from the Institute of WorkComp Professionals during a recent Power Producers Podcast. Kevin joined David Carothers to honor the contributions of industry legend Preston Diamond and explore how his wisdom still applies in today’s sales landscape.
Please confirm you want to block this member.
You will no longer be able to:
Please note: This action will also remove this member from your connections and send a report to the site admin. Please allow a few minutes for this process to complete.
Responses