Data-Driven Sales & Private Equity

Kevin Davis and I spent this episode of the BoogieBoard Tiki Lounge tracing a path that started in the late 90s in the White House's Office of Scheduling and Advance, where my actual job was building briefing books three or four weeks ahead of every presidential stop — essentially the manual, fax-machine version of what AI meeting prep does in two minutes today. Kevin joked that I was the original AI, and honestly, that's not far off.

We spent a good chunk of the conversation on territory design, which I think is the most underrated lever a CRO has. Early in my career, I inherited a team where one seller — who happened to be his manager's neighbor and best friend — was credited as the best rep in the company, retiring at 180% of quota. When I actually dug into the data, it turned out 90% of his industry's headquarters sat inside his territory alone; the rest of the team was fighting over the remaining 10% of the market. Once we redesigned the territories evenly, he became the lowest performer on the team, and the sellers who'd actually been good at selling finally had the chance to prove it. Territory design is the great equalizer — it's what separates the people genuinely winning from the people just collecting bluebirds.

We also talked about the discipline of moving from anecdote to evidence, something I had to learn the hard way moving from sales into marketing leadership: data isn't the plural of anecdote, and a leader who extrapolates from their last deal instead of the last few hundred opportunities is going to build the wrong plan. That rigor is the whole premise of The CRO's Guide to Winning in Private Equity — replacing gut calls with a documented process you can actually defend in the boardroom.