How Private Equity Evaluates CROs with JD Miller

Warren Zenna asked me something nobody else has on a podcast: what did being a licensed food sanitation manager teach me about leadership that the boardroom never did. It's a fair question — I'm also the guy who ran kitchen operations for Care for Friends, the Chicago homeless nonprofit, and gets recertified in safe fish handling every four years alongside my day job advising private equity boards.

We spent most of the conversation on what I call the system-inheritor problem: CROs get hired into companies where the systems are already broken, and they don't have the authority to have built them differently. The fix isn't heroics, it's a one-page plan — a single sheet that lines up new logo, renewal, and churn assumptions with the board before the year starts, so a missed number becomes a data point instead of an ambush. I also told Warren about the loss-interview discipline I run in every company I lead — hiring an independent third party to call losing prospects, because a salesperson will tell you the price was too high and a customer will actually tell you the sales team felt like used-car salesmen.

The best predictor of future performance is past performance, which is exactly why boards get nervous when a CRO can't explain the gap between the plan and the result. I've now evaluated 158 AI sales tools for my second book, and the ones worth using are the ones that make you show up more human in the room, not less.