What I Told the New CFO First
Day one, he asked what to look at before the board meeting in two weeks. I told him three things, none of them in the model he'd been sent.
"What should I look at before the board?" the new CFO asked on day one. The board met in two weeks. I gave him three things, none of them in the model he had been sent.
First, the two customers I would be least surprised to lose at their next renewal. Both sat in the top ten by revenue. Neither showed up on any retention dashboard. Each had a specific reason, a champion who had left, a workflow change inside the customer that pushed our product to the edge, that I knew from CSM calls and the CRM never recorded. Together they were 12 percent of revenue, spread across two contracts the model treated as safe. It is the kind of exposure I wrote about in the customer concentration nobody named.
Second, the three deals the reps had marked commit that I would not personally bet on. Each had a tell: a procurement delay with no clean path, a champion who had gone quiet, a buyer asking for terms the deal could not honestly carry. The committed number was 4.8 million dollars. The number I would have wagered on was closer to 3.6 million. That gap was the CFO's first real surprise, the same gap that shows up when a pipeline is marked seventy percent won.
Third, the lines in the model where finance's estimates were soft. Customer success cost-to-serve was understated, because the team was absorbing complexity no one had costed. Hosting was understated, because the projection ran off last year's contract, which was up for renegotiation at worse terms. Two line items, undercosted together by about 400,000 dollars against the year.
The model the new CFO received was accurate as far as it went. The three things I told him were what it could not yet see. That disclosure is what compresses a new CFO's ramp from a quarter to a month. Without it, he finds each one alone, usually after the board meeting has already happened, while he runs on the clean version the model shows.
The discipline is uncomfortable. Telling a new CFO which numbers I distrust means admitting which numbers I have let the board see anyway. That admission is the price of getting him useful sooner. Most founders defer it, and pay the deferral back in ramp time.