The CRO Lifecycle | Revenue Rebels

Max Greenwald opened our conversation on Revenue Rebels by asking about Chicago's Most Inspiring Individual award, not about revenue at all. Fourteen years ago I started volunteering at a homeless shelter down the street that was going broke, spending $2 million of a small church's budget to run it. We spun it off as its own nonprofit, called it Care for Friends, and this year opened a new $10 million facility right in Lincoln Park. We now see about 12,000 homeless guests a year and get most of them housed within six months of first contact.

From there we got into the harder math of scaling a company from $3 million to $10 million in revenue, which is right where Max's own company, Warmly, sits today. My advice to him: the things you had to do to get to a million and to three are generally the opposite of what gets you to ten. His head of revenue, Keegan, is a great seller and still close to every key deal, but past the ten-million mark nobody can personally be in every deal, and holding onto that habit becomes the ceiling on how big the company can get.

We also talked about why the average CRO now lasts about 18 months in the seat. It's rarely because they missed the number; it's because they weren't able to tell the board what the number was going to be early enough for anyone to react. It's okay to tell us it's raining outside — what we need is an informed view of how much longer we need our umbrellas out. The CROs who last are the ones who give their boards time and visibility, not just results.

We closed on the founder's side of that same equation: the moment a CEO has to delegate every piece of work down to the lowest-paid person capable of doing it, freeing themselves up for the vision, strategy, and investor conversations that only they can have.