Driving Business through Curious Leadership with Jon Bassford, Episode #384

In today’s competitive insurance marketplace, middle-market agencies must leverage every available advantage to win and retain business. One of the most underutilized yet powerful resources at an agent’s disposal is the wholesale market. By establishing strong partnerships with wholesalers, agents can access capacity, expertise, and proprietary programs that are often unavailable through direct channels. However, success in the wholesale arena requires more than simply submitting risks and hoping for the best.

In the fast-paced world of commercial insurance, where every hour counts and every interaction matters, producers and agency owners are turning to artificial intelligence not as a replacement for human connection—but as a force multiplier. AI tools like ChatGPT are no longer just novelties or futuristic concepts. They are strategic business assets, helping commercial producers streamline workflows, scale personalization, and reclaim valuable time.

Most commercial insurance producers fail not because they lack talent, but because they lack a plan. They enter the year with vague production targets—usually handed down from management—and hope that pure effort or luck will lead to success. But in the middle market, hope is not a strategy.

If you want to build a book of business that produces consistent results and long-term revenue, you need to think like a business owner. That means developing a business plan that is personal, measurable, and rooted in data. In this post, we’re going to show you how to reverse engineer your sales goals, simplify your sales pipeline, and build a weekly rhythm that supports growth without burnout.

When it comes to retaining large, high-value clients in the middle market, captive insurance should be one of the first solutions every producer considers. Yet many agents avoid the topic entirely—often for reasons that have less to do with the client’s needs and more to do with the producer’s own hesitations.

The truth? Failing to offer captives could cost you a $300,000 revenue client overnight. And in today’s competitive market, someone else will step in and take that account if you don’t.

In this post, we’ll break down the three biggest mental roadblocks holding agents back from selling captives, show you how to address them, and explain how to position yourself as the quarterback of the client relationship—while increasing your value and your compensation.

Middle market insurance producers face a “sleeping giant” opportunity in professional lines—namely cyber insurance, management liability (Directors & Officers and Employment Practices Liability), and broader professional liability coverages. Too often, these critical products are treated as afterthoughts, tacked onto a renewal packet rather than leveraged as strategic revenue drivers and client-retention tools. In this comprehensive guide, we’ll explore why professional lines deserve your full attention, how to overcome common obstacles, and which actionable strategies will unlock growth across your book of business.

The landscape of commercial insurance is evolving at an unprecedented pace. As agencies strive to serve middle-market clients more effectively, many find themselves asking: how can we harness the power of AI in insurance to streamline operations, reduce errors, and free up producers for high-value tasks?

In this deep dive, we’ll explore the two fundamental pillars of AI—generative and analytical—outline practical steps for embedding automation into repeatable workflows, examine real-world case studies, and offer guidance on security, vendor selection, and change management. Whether you’re a curious producer or an operations leader, this post will give you actionable insights to start small and build momentum toward a more efficient, technology-enabled future.