The Waymaker with Stuart Leo, Episode #181

Middle-mazrket businesses face unique challenges when it comes to managing their workers’ compensation programs. Unlike large enterprises, they often lack dedicated in-house resources for safety, compliance, and claims oversight; yet unlike small businesses, their scale subjects them to more sophisticated regulatory scrutiny and larger potential losses. In this environment, commercial insurance producers who master an integrated approach—combining precise prospecting data, impactful compliance applications, and exceptional claims handling—can both win new accounts and build lasting client relationships.

In the most challenging insurance market many of us have ever seen, independent agencies are grappling with a familiar foe: limited carrier access. Whether you’re a former captive agent trying to break into the independent space or a small agency trying to grow your commercial book, the obstacles are real. Direct appointments are hard to come by, especially for shops under $5 million in revenue, and wholesale markets can feel intimidating or like a last resort.

But they don’t have to be. With the right partner, wholesale and brokerage relationships can become a strategic advantage, not just a stopgap. This post explores how agencies can leverage smart market access to grow confidently, preserve profitability, and position themselves for long-term success.

The insurance industry is undergoing a profound transformation as middle-market agencies recognize the benefits and challenges of embracing a fully remote workforce. No longer viewed as a temporary workaround, remote models offer the potential to tap into nationwide and offshore talent pools, reduce overhead, and increase flexibility in an increasingly digital world. Yet, flipping the switch to virtual operations can expose gaps in documentation, dilute corporate culture, and strain traditional oversight mechanisms. In this post, we’ll explore the four pillars essential to building a high-performing remote insurance team—core values, hiring practices, onboarding processes, and KPI strategies—while also delving into best practices for managing domestic versus offshore employees, ensuring data security, leveraging productivity tools, and fostering trust and autonomy.

In today’s hard commercial insurance market, middle market business owners are more open than ever to solutions that give them greater control over their insurance costs. While guaranteed cost programs remain the default option, they often lack the flexibility and long-term savings that high-performing businesses crave. That’s where captive insurance comes in—a powerful but often misunderstood tool that enables clients to turn insurance from a sunk cost into a strategic asset.

Middle-market insurance agencies have long wrestled with the legacy “buy-bill-collect” model, in which carriers invoice agencies, agencies collect premiums from clients, and only then remit payment to carriers. This antiquated workflow creates operational friction, delayed cash flow, and elevated chargeback risks—all of which can erode profitability and client satisfaction. Today, however, powerful innovations in digital payments and agency management systems are enabling a modern “bill-collect-buy” paradigm that dramatically accelerates fund availability, minimizes disputes, and unlocks new revenue streams through premium financing.

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.