About Jon Webb

39 Years. Every Sales Job. One Standard.

Jon Webb is an Indiana State University 1987 graduate and Founder & Lead Principal of Major League Selling LLC.

Major League Selling wasn’t built in a classroom. It was forged over nearly four decades in the trenches — carrying a bag, leading teams, and eventually serving as Chief Commercial Officer — then writing the field manual he wished he’d had on day one.

I spent the first half of my career making the same mistakes every seller makes. Pitching when I should have been listening. Convincing when I should have been diagnosing. Then I met Paul Cherry — author of Questions That Sell — and something shifted. The best sellers aren’t closers. They are diagnosticians.

That insight changed everything. Major League Selling and Selling Against NO! are the result.

We don’t just diagnose deals; we install the habits required to WIN THE DAY!

Today, Jon speaks at national sales meetings, company events and industry conferences, and leads Major League Selling masterclasses.

Featured in Investor’s Business Daily and The Republic. See Media

The Ethos

We operate by one rule: Help, Serve & Influence. We don’t pitch — we diagnose. We don’t close deals — we open relationships that compound over time.

The Mission

We specialize in making the invisible Cost of Inaction visible to the buyer — turning stalled deals into strategic commitments. Our operating philosophy: Help, Serve & Influence. Not pressure. Not manipulation. Diagnosis.