There is a moment when every founder recognizes that it’s most likely time to hire someone to direct sales efforts. Revenue is growing and the pipeline is filling while trying to build the product and operate the organization that’s in place. All too often owners who are in this position throw an ad on a site, hire an individual who seems to fit their notion of a fit, and within eighteen months let them go.
Every year, in conference rooms and video calls across the country, sales leaders perform a very familiar ritual. Last year’s numbers are gathered and a growth percentage is tacked on that will presumably satisfy the board. This is then divide it by the number of reps in the organization and a quota number is reached.
The Chief Revenue Officer is among the most consequential hires a tech company can make, and among the most frequently botched. That mismatch is expensive, and it’s almost always avoidable. This is not because boards lack intelligence or seriousness, but often this comes about due to the fact that the role is genuinely complex, the signals are easy to misread, and the pressure to fill the seat quickly tends to compress exactly the kind of deliberate, rigorous thinking the decision demands.