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

The insurance industry isn’t known for flash or flair. Most people picture gray suits, paperwork, and words like “renewal,” “loss runs,” or “premium audit.” But a new generation of producers is proving that this business doesn’t have to be boring. They’re showing that authenticity, energy, and creativity can make insurance not only engaging but a platform for meaningful connection and career fulfillment.

The world of commercial insurance is evolving rapidly. It’s no longer just about quoting policies and hoping for renewals. Today, producers have the opportunity to lead with value, bring strategy to the sales process, and create long-lasting client relationships that transcend policy pricing.

In the ever-evolving world of commercial insurance, marketing has become a critical lever for growth. Yet most agencies still struggle to understand what’s actually working. From websites that generate leads with no attribution to CRM systems that silo vital data, insurance agencies are often flying blind.

If you’re a commercial insurance producer trying to grow in the middle market, you’re probably aware that the old-school prospecting methods—cold calling hundreds of businesses, dropping off trinkets, hoping someone is “coming up on renewal”—are no longer enough. In today’s competitive environment, success isn’t about how many people you reach. It’s about reaching the right people at the right time with the right message.

Too many agents stop learning once they’ve earned their license. The bare minimum—meeting continuing education requirements—is not enough in today’s climate. Producers often resort to online forums, asking where they can complete CE hours “as quickly as possible.” This mindset directly impacts their ability to communicate complex subjects like reinsurance or risk modeling to clients in an understandable way. As a result, they struggle to retain accounts and close new business in an increasingly competitive market.

The problem? Too many producers are pitching too soon, to the wrong people, with nothing more than a quote to offer. This article walks through how to close more business by positioning yourself as a trusted advisor, selling Total Cost of Risk (TCOR) outcomes, and using a structured approach to differentiate at every stage of the sales process.