An Interview with the Headmaster with Jim Schubert, Episode #185

The cyber insurance market has softened in recent years. Requirements that were once rigid — like mandatory multi-factor authentication (MFA) or endpoint detection and response (EDR) tools — have been relaxed by many carriers. But here’s the danger: just because carriers aren’t demanding these safeguards today doesn’t mean businesses can afford to ignore them.

The insurance industry is entering one of the most transformative seasons in its history. For decades, our world has been shaped by carriers, underwriting cycles, prospecting methods, and the grit of producers willing to outwork their competition. But today, a new force is reshaping the landscape—and most producers, agency leaders, and industry professionals aren’t ready for it.

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.