Jerry Brooner is a four-time Chief Revenue Officer who has built and scaled revenue organizations through some of the defining moments in modern enterprise tech. He stood up the strategic enterprise team at Dropbox and led it through its IPO, was the founding CRO at Scout RFP through its acquisition by Workday, served as president of global field operations at Enable from Series A to unicorn, and most recently drove 4X ARR growth as CRO of AI-native procurement platform Levelpath. He calls himself a 'late CRO': before ever carrying a quota, he deliberately rotated through operations, marketing, partnerships, consulting, sales ops, and product — a diverse foundation he credits for making him a more effective revenue leader. Earlier in his career he spent roughly a decade at SAP running large enterprise deals, went through his first IPO at Callidus, and was acquired at Siebel Systems (bought by Oracle).
“The ones that I found that really had an impact on their business understood the whole business.”
“One of the fundamental skills people are lacking, especially younger generations, is the ability to pick up the phone and call somebody — and even more so now in the AI age, that's a fundamental skill.”
“As long as you are learning something in your job, you should stay there and learn that skill.”
“It taught me how to converge at volume and velocity product-led growth into an enterprise sales motion.”
“My mantra that my team became: if we're in a competitive sales cycle against Box, one of us is in the wrong cycle — and it's probably us.”
“Don't improve your weaknesses. Ignore your weaknesses. Know what they are, and then be like, I'm not going to go there.”
“Everyone knows the roadshow. But before any of that happens, there's a secret roadshow — every exec is flying on different jets, it's like an event somewhere that's not really an event.”
“You've got to tell Wall Street about everything, or things go bad. No one loves surprises — no one — but especially Wall Street.”