Your book of business is under constant attack. Competitors are targeting your best accounts every day, just like cybercriminals probing a website for vulnerabilities. If you don’t have a plan to defend and grow your client relationships, you’re leaving yourself exposed.
One of the most effective tools to protect and retain your best clients—especially in the middle market—is captive insurance. But here’s the key: captives are not just another market option to toss into the mix at renewal. They are a long-term business continuity strategy designed to keep you in control of your book while positioning you as a trusted strategic advisor.
This blog features insights from Warren Cleveland from Captive Coalition.
Think of your book of business like a website. Even when you’re not aware of it, competitors are working to find weaknesses—whether that’s pricing, service gaps, or perceived lack of expertise. The moment they spot an opening, they’ll pounce.
The truth is, in a hard market, this competitive pressure only intensifies. If your retention plan is simply “hope the client stays,” you’re gambling with your income. Captive insurance gives you a defensive moat around your best accounts, making it harder for competitors to create a compelling reason for your clients to leave.
More Than Just Another Market
Captives are often misunderstood. Many producers think they’re just an alternative market to quote against traditional carriers. That’s a mistake. Captives should never be pitched as a quick fix or a “silver bullet” to save on premiums.
When sold correctly, captives are about stability, control, and transparency—not chasing a cheaper price. They create a long-term partnership between you and your client, where the relationship is no longer tied to the whims of the traditional insurance market.
The Client-for-Life Factor
Once a client is in a well-performing captive, there’s little incentive for them to leave. Moving from one captive to another requires significant new collateral and provides minimal competitive advantage if performance is strong.
For the producer, that means long-term client retention. For the client, it means predictable costs, transparency in where every premium dollar goes, and a risk management strategy that rewards good performance over time.
Common Producer and Agency Owner Missteps
Even top agencies sometimes miss the captive opportunity. Common mistakes include:
When you avoid captives out of fear or lack of knowledge, you leave your book vulnerable to producers who do understand and can sell the long-term strategic benefits.
The best time to introduce captives is 90 days after renewal—when the client isn’t distracted by immediate insurance decisions and you have their full attention.
From there, you should begin a drip education process that builds understanding and trust over time. This includes explaining collateral requirements, the long-term return timeline, and the strategic advantages.
Clients should know months—if not a full year—in advance how captives work before they’re ever asked to commit significant capital.
What Strategic Advisors Do Differently
Most producers are seen as salespeople because they tie their value to the product they deliver. Strategic advisors, on the other hand, sell their intellectual capital and processes—and they win more often because of it.
Strategic advisors are called before big decisions are made. They’re part of the client’s planning process, helping map out growth strategies, risk management approaches, and cost-control methods.
The Business Owner Mindset
Successful business owners don’t write six-figure checks on a whim. They take calculated risks based on trust, education, and clear ROI. Your job as a producer is to guide them through that decision process so they feel confident in the strategy.
For producers: Start planting the seeds about captives well before renewal. Build the narrative around stability, control, and strategic growth—not just pricing.
For business owners: Ask your current broker if they’ve explored captives for your business. If they haven’t, that’s a red flag that they might not be thinking long-term about your risk management.
The producers who will dominate the next decade aren’t the ones who can “find a cheaper quote.” They’re the ones who operate as strategic advisors—helping clients make informed, proactive decisions about managing risk.
Captive insurance isn’t for everyone, but for the right client, it’s the ultimate retention tool, growth strategy, and business continuity plan rolled into one.
If you want to protect your book, deepen client relationships, and compete on value instead of price, it’s time to add captive insurance to your playbook—before your competitors do.
The commercial insurance world isn’t for the faint of heart. It’s unpredictable, chaotic, and constantly demanding producers to manage competing pressures—client needs, renewal deadlines, life events, prospecting goals, and agency responsibilities. And if you’re a middle-market producer, multiply that by ten.
In the middle market commercial insurance space, the role of the producer has never been more critical—or more misunderstood. Too many producers still view their job as selling policies instead of what it truly is: protecting the assets and livelihoods of the businesses they serve.
The middle market rewards depth, not breadth. Yet many producers still approach it like a volume game, quoting everything that moves, chasing price, and hoping activity turns into production. From the outside, it looks like hustle. From the inside of the underwriting and wholesale world, it looks like noise.
Personal lines has quietly become one of the most competitive segments in the insurance industry. Agencies that once dominated their local markets are now fighting to differentiate themselves against direct writers, digital-first carriers, and large brokers with massive content machines.
The cyber insurance market has always been unpredictable. Over the past decade, we’ve seen it move from an emerging line of coverage to one of the most volatile, swinging rapidly between soft and hard market cycles. But today, cyber has entered one of the softest markets in recent memory—and that presents a rare opportunity for both agents and clients.
For most of my 20-year career, captives felt like something reserved for the insurance elite—the jumbo accounts, the Fortune-level operations, the companies with multimillion-dollar manual premiums and entire departments dedicated to risk management. If you had asked me ten or fifteen years ago whether a $250,000 account was a legitimate captive candidate, I would’ve laughed. I thought captives were reserved for companies so complex and so large that the only rational way to insure them was to build an insurance company around their risk.
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