This is probably the most commonly discussed paradigm in The Innovator’s Dilemma – academic Clayton Christensen’s influential paper on how large existing companies can become too dependent on existing customers and processes, and ultimately lose market share to competitors. For Tony Capasso, this framework runs through the financial lifeblood of any business: revenue.
Like product and engineering organizations, sales teams can be “stuck in the same golden goose dilemma of product and revenue streams,” he said. Over time, it becomes increasingly difficult to allocate resources to new opportunities, even if they are crystal clear.
“Part of it is understaffing,” Capasso said. “All my employees are busy, and they’re working on core stuff. There might be something new that they’re not trained for, or that’s hard to learn. Ultimately that’s what leads to risk. It’s the opportunity cost of pulling someone out of the core job to do a new job. That’s the revenue dilemma. It asks: How do we expand our possibilities and get to places we’re not currently going without destroying the entire machine?”
Capasso played professional football (and coached at UT Austin) before holding sales and revenue leadership roles at Austin startups like Bazaarvoice. He believes AI has the unique ability to help sales teams “find the money” by automating sales interactions.
“I want to challenge the assumption that we need to put humans in the middle of everything in order for users to derive huge benefit from it,” he told us wealth. “I think actually in a lot of interactions, users don’t want to talk to people… It’s not about perfection. It’s about giving users what they need in the moment.”
Capasso co-founded OnProfit in 2024 with Alan Lockett, David Rubin, and Matt Stuart to build AI tools that unlock “discovery dollars” that are currently languishing due to unexecuted initiatives, underutilized products, or gaps in sales and customer coverage. Today, the Austin-based company is quietly emerging, with current clients including HomeStory, OEConnection and Commerce. OnProfit is backed by Lerer Hippeau, SignalFire and Mark VC, from whom it quietly raised a seed round in 2024. (It declined to disclose the amount raised.)
“We focus on businesses because, fundamentally, they are the greatest opportunities for revenue and capital,” Capasso said. “Our value proposition is that there is an inherent coverage problem, which is a mismatch between the opportunity and the resources to pursue that opportunity.”
HomeStory President Chad Bockius has been working hard to solve this problem and work on optimizing the sales channel of the real estate brokerage platform. It’s basically impossible to build a system where no customers slip through the cracks at the fragile beginning of the sales process.
“I knew I was leaving money on the table, but it just didn’t work out financially,” Bockius said. “I just can’t hire enough people to solve the problem. So, I just live with it and hate the metric.”
Bockius, who hired Capasso for his first sales job, said using OnProfit’s platform “increased connection rates by 10% and ultimately increased revenue by about 20%.”
It’s not that most revenue teams are doing anything wrong, it’s just that the basics of sales and revenue management require a lot of coordination. Jim Stoneham, a partner at SignalFire and former head of growth at New Relic, said revenue struggles were part of his life for years.
“A lot of revenue teams are just trying to keep the basics working well, with revenue cycles coming up and upgrade opportunities associated with new product launches,” said Stoneham, former chief marketing officer at Stripe. “These may seem trivial…but often they are not. You need ten people in a room to make anything happen.”
There’s no shortage of potential competitors in the space (basically everyone is applying AI to their revenue and sales stacks). Adam Zeplain, co-founder and managing partner of Mark VC, said that while artificial intelligence may be the answer, by nature, these problems cannot be solved by technology alone.
“These are business issues,” he said. “These are not technology problems. You need to understand exactly the business problems these companies need to solve. It’s the same technology, but there’s no one-size-fits-all solution.”
When I saw Capasso, he had OnProfit gadgets on him, but no company name displayed. Instead, the hat says “Found Money Club.” This is intentional.
“Who doesn’t want to join the Found Money Club?” Capasso laughed.
See you tomorrow,
Ellie Garfunkel
X:@agarfinks
e-mail:alexandra.garfinkle@fortune.com
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venture capital deals
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