Insurance Agency 4.0 with Matt Masiello, Episode #93

The truth about professional sales isn’t flashy, and it certainly isn’t about charisma. If you think selling is about having the “gift of gab,” winging it on calls, or leaning on your likability to win deals, you’re doing it wrong—and that’s why you’re struggling. In this post, we’re breaking down lessons from a brutally honest conversation with Benjamin Dennehy, the UK’s Most Hated Sales Trainer®, about why so many producers in commercial insurance and other industries fall short—and what the top performers do differently.

Middle market producers often believe that bigger accounts come from quoting better, faster, or cheaper. But in reality, the leap from writing $5,000 policies to closing $1.2 million in premium starts with a different mindset. It starts with consulting over quoting. That’s exactly the story that unfolded at Producers in Paradise when Doug Benz shared how he landed the largest account of his career—not by selling insurance, but by solving problems no one else could.

This post breaks down the step-by-step strategy Doug and his mentor David Carothers used to win a high-stakes, complex account through total cost of risk analysis, claims data visibility, and certificate compliance solutions. If you’re a commercial producer trying to break into the middle market, this blueprint is for you.

At Producers in Paradise 2025, five insurance leaders took the stage to share exactly how they’ve built brands that drive real conversations and real revenue: Patrick McBride, David Carothers, Ciara Gravier, Daniel Wakefield, and Aaron Levine.

In a constantly evolving insurance landscape, commercial producers are being forced to adapt—quickly. Between InsurTech advancements, shifting market conditions, and increasing client expectations, producers must learn how to balance innovation with deep relationship-building and technical risk expertise. On a recent episode of the Power Producers Podcast, industry veteran David Carothers sat down with Brett Fulmer, principal at Newport Beach Insurance Center, to talk about navigating these dynamics with authenticity and strategy. What followed was a roadmap for producers who want to succeed in today’s middle market.

In the commercial insurance industry, success can come fast—especially for driven producers who are focused on the middle market. The money starts coming in, the book grows, and you find yourself standing in rooms where you once only dreamed of being. But with that success comes a subtle trap—one that’s caught more than a few top producers off guard: arrogance.

It’s not always loud or obvious. Sometimes, it’s the silent erosion of empathy. Other times, it’s the misplaced belief that your way is the only way. In this post, I want to explore how insurance producers can stay grounded even as their careers take off, how they can build respect by honoring where they came from, and how to avoid becoming the very kind of producer people whisper about after conferences for all the wrong reasons.

In the world of commercial insurance, no phrase inspires more dread—or confusion—than “workers’ comp audit.” Often, the root cause of these audits isn’t fraud or underreporting, but something far more preventable: incorrect workers’ compensation class codes.