In this episode of Power Producers Shoptalk, host David Carothers
kicks off a new series on captive insurance with special guest Warren
Cleveland of Captive
Coalition. They dive into the critical dilemma facing insurance agents
today: the risk of losing their best clients to competitors who offer captive
solutions. David
and Warren
discuss why many agents are unaware or unprepared for this threat, leaving
their top accounts vulnerable. The conversation focuses on the necessity of
being proactive, identifying the right opportunities for captives, and
integrating this conversation into an agent’s workflow to protect and grow
their book of business.
Warren
Cleveland shares a personal story of losing a $300,000 revenue client,
not because of poor service, but because he couldn’t offer the captive
solution they needed. The discussion highlights that the biggest clients are
actively being targeted, and business owners are seeking solutions for the lack
of transparency and control in the traditional insurance market.
The conversation stresses the importance of initiating the captive
conversation before a competitor does. David and Warren
explain that if an agent has to react to a client’s question about captives,
they are already in a defensive position and have likely lost control of the
relationship.
The episode outlines the ideal profile for a captive
prospect: typically businesses spending $250,000 or more in casualty premium
with a good loss history and a commitment to risk management. They
strongly advise that these conversations should not happen at renewal but
rather as part of a forward-looking, strategic discussion during events like
quarterly claims reviews.
David
explains how leveraging captives can allow agents to expand their
geographic footprint and dominate a specific niche, like HVAC contractors. By
becoming the expert, an agent can build a substantial book of business by
targeting middle-market accounts that other agents are neglecting.
If agents don’t bring up captives, frustrated
business owners will search for solutions themselves. Warren notes that
many captive managers are ready to work directly with these business
owners, cutting the original agent out of the picture entirely. The key
takeaway is that agents must own and control the conversation.
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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