The startup betting AI can unlock a new era of ‘found money’ for enterprises

This model is perhaps most commonly discussed in the context of the Innovator’s Dilemma – academic Clayton Christensen’s influential thesis about how large, incumbent companies become attached to existing customers and processes, and ultimately lose market share to competitors. For Tony Capasso, this framework extends to the financial lifeblood of any business: revenue.

Like product and engineering organizations, sales teams can “stumble upon the same golden goose for their product and revenue stream,” he says. Over time, it becomes difficult to allocate resources to new opportunities, even if they are quite obvious.

“Part of what it looks like is not having enough people,” Capasso said. “All employees are busy, and they’re all working on essential things. There may be new things that they’re not trained on or that are difficult to learn. And that’s ultimately what creates risk. It’s the opportunity cost of pulling someone from something essential to work on something new. That’s the revenue dilemma. It’s asking: How can we expand our capabilities and go places we’re not currently going, without disrupting the whole machine?”

Capasso—who played professional football (and coached at the University of Texas at Austin) before moving on to lead sales and revenue at Austin startups like Bazaarvoice—believes that AI is uniquely equipped to help sales teams “find the money” by automating sales interactions.

“I want to challenge the assumption that we need to put the human in the middle of everything for the user to get significant benefit from it,” he said. luck. “I think there are already a lot of interactions where a user would rather not talk to a human being… It’s not about perfection. It’s about getting what that user needs in the moment.”

Capasso started OnProfit in 2024 with Alan Luckett, David Rubin, and Matt Stewart to build AI tools that unlock “found money” — revenue that is currently left on the table due to half-executed initiatives, underutilized products, or gaps in sales and customer coverage. Today, the Austin-based company is coming out of stealth, with a list of clients that currently includes 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 enterprises because they represent the greatest opportunities for revenue generated and money earned,” Capasso said. “Our value proposition is in situations where there is a built-in coverage problem, a mismatch between the opportunity and the resources needed to exploit that opportunity.”

HomeStory president Chad Bockius has grappled with this, working to improve the real estate brokerage platform’s sales funnel. It’s basically impossible to create a system where no customer fails at a poor start to the sales process.

“I know I’m leaving money on the table, but the economy isn’t working,” Bockius said. “I can’t hire enough people to solve this problem. So, I lived with it and hated the scale.”

Using the OnProfit platform resulted in “a 10% improvement in…contact rate, and…that translates to about a 20% increase in revenue in the end,” said Bockius, who hired Capasso for his first sales job.

This isn’t to say 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 SignalFire partner and former head of growth at New Relic, said the revenue dilemma has been his life for years.

“A lot of revenue teams are just trying to keep the basics working well, the next revenue cycle, and the opportunity to upgrade associated with a new product release,” said Stoneham, who is also Stripe’s former CMO. “These things seem trivial… but they usually aren’t. You need to get ten people in one room to achieve anything.”

There is no shortage of potential competitors in this space (basically everyone applying AI to revenue and sales groups). Adam Zeppelin, co-founder and managing partner of Mark VC, said that while AI may be the answer, at its core, they are not problems that can be solved with technology alone.

“These are commercial problems,” he added. “These are not technology problems. You need to understand exactly the business problems these companies need to solve. It’s the technology itself, but there are no one-size-fits-all solutions.”

When I see Capasso, he has an OnProfit swag that doesn’t have the company name on it. Instead, the hat says “Found Money Club.” This is intentional.

“Who doesn’t want to join the Found Money Club?” Capasso laughs.

see you tomorrow,

Allie Garfinkel
tenth:@agarfinks
Email:alexandra.garfinkle@fortune.com
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