What are You Really Worth with Legacy Advisors, Episode #283

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.

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.

The commercial insurance landscape is evolving—fast. As the market hardens across many lines, producers are learning that generalist approaches no longer cut it. Wholesale partners who specialize, who truly live and breathe their niche, are not just valuable—they’re essential.

That’s where professionals like Dylan Jordan and his team at Amwins come in. With a laser focus on medical malpractice, human services, and life sciences, they’ve become go-to problem solvers for agents navigating the most difficult-to-place risks. If you’re a retail agent walking away from complex accounts—or worse, mishandling them—it might be time to rethink your strategy.