Presales to CRO | Software Sales Simplified

Matt Long has known me for more than 25 years — we met as two of the first sales engineers ever hired at a Chicago startup called Introspect, back when I was still finishing a PhD in communication and had already given up on becoming a lawyer or a philosopher. On Software Sales Simplified, Matt and Kevin Donville and I traced that whole arc, including how a degree spent studying online social networks turned into a career reading rooms full of enterprise buyers.

The turning point from SE to AE came when I realized I was doing most of the work on every deal and making half the commission of the AE I was partnered with. The only two things standing between me and that paycheck were cold calling and contract negotiation, so I raised my hand and learned both. My dad, a surgeon, taught me the framework I still use to train sellers today: watch one, do one, teach one.

We spent a good chunk of the episode on what it's like advising private equity firms, which I compare to flipping a house — buy something with good bones, do the work, sell it for more a few years later. I told the story of two competitors, Runzheimer and Motus, pitching the exact same vehicle-reimbursement product: one walked customers through an hour of data-collection methodology, and the other closed the identical deal in ten minutes with a single slide. Being too close to your own solution is expensive; sometimes the most valuable thing an outside advisor does is boil ten minutes of real value out of an hour-long pitch.

That instinct for pattern recognition, knowing which parts of a pitch, a forecast, or a growth plan actually matter, is what The CRO's Guide to Winning in Private Equity is built around.