Leaving Captivity with James Jenkins, Episode #263

Reinvention is one of the most powerful themes in the insurance industry. Some of the best commercial producers in the country did not grow up wanting to sell insurance. They did not study risk management in college. They did not come from an agency family. They found this industry after they tried something else. They found it after life pushed them toward a career where performance, autonomy, and mindset determine the outcome.

The most successful producers in the middle market did not get there because they quoted faster, smiled bigger, or knew how to talk longer. They got there because they learned how to differentiate themselves so clearly that prospects had no choice but to see them as trusted advisors. They learned to operate like businesspeople first and insurance technicians second. They learned how to tie operational mechanics to insurance outcomes. They learned how to control their time, their pipeline, and their future.

In commercial insurance, the most dangerous threats to your book of business aren’t always visible on the loss runs. One of the most overlooked vulnerabilities for middle market producers is ignoring the personal lines needs of their business owner and executive clients.

The commercial insurance industry is one of the few professions where someone can enter with no experience, no connections, and no background in risk management and still build a long, lucrative career. But success is never automatic. It requires hunger, humility, curiosity, and the willingness to keep showing up even when the process feels overwhelming. That is why the story of Pam Seidler has already started making waves among new and aspiring commercial producers.

In an industry where tradition often outweighs innovation, artificial intelligence and automation are slowly but steadily reshaping how independent insurance agencies operate. The push toward smarter, more efficient workflows is no longer a matter of if—but when. While many agencies are still evaluating how AI fits into their operations, early adopters are already reaping the benefits of streamlined submissions, faster processing, and actionable data insights.

The commercial insurance industry is changing faster than ever—and not always for the better. Consolidation is accelerating. Service levels are declining. Private equity is pushing agencies to scale in ways that strip out the personal touch that once defined the independent channel. But for the producers willing to do the work, lean into mentorship, and sharpen their craft, this isn’t a challenge—it’s an opportunity.