Success can be a trap.
It’s a paradigm perhaps most commonly discussed in the context of the Innovator’s Dilemma—academic Clayton Christensen’s influential thesis around how large incumbent companies become too tied to existing customers and processes, and ultimately lose market share to competitors. To Tony Capasso, this framework carries through to the financial lifeblood of any business: revenue.
He says that, like product and engineering orgs, sales teams can “get stuck on the same golden goose of their product and revenue stream.” Over time, it gets harder to allocate resources to new opportunities, even if they’re crystal clear.
“Part of what that looks like is not having enough people,” said Capasso. “All my people are busy, and they’re all working on the core stuff. There may be new things they’re not trained on or that are hard to learn. And ultimately that’s what leads to risk. It’s the opportunity cost to pull someone off something core to work on something new. That’s the revenue dilemma. It’s asking: How do we expand our possibilities and go places we’re not currently going, without disrupting the whole machine?”
Capasso—who played professional soccer (and coached at UT Austin) before moving into sales and revenue leadership at Austin-based startups like Bazaarvoice—believes AI is uniquely equipped to help sales teams “find money” by automating sales interactions.






