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.

“I want to challenge the assumption that we need to put a human in the middle of everything for a user to get great benefit from that,” he told Fortune. “I think there are actually a lot of interactions where the user would prefer not to talk to a human… It’s not about perfection. It’s about getting that user what they need in the moment.”

Capasso started OnProfit in 2024 with Alan Lockett, David Rubin, and Matt Stuart to build AI tools that unlock “found money”—revenue that is currently being left on the table due to unexecuted initiatives, underutilized products, or gaps in sales and customer coverage. Today, the Austin-based company is emerging from stealth, with a roster of customers currently 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’re focused on enterprises because fundamentally, they’re the biggest opportunities for this found revenue, found money,” said Capasso. “Our value proposition is where there’s a built-in coverage problem, a mismatch between opportunity and the resources to go after that opportunity.”

HomeStory president Chad Bockius has wrestled with this, working to optimize the real estate brokerage platform’s sales funnel. It’s essentially impossible to set up a system where no customer falls through the cracks at the vulnerable beginning of a sales process. 

“I know I’m leaving money on the table, but the economics don’t work,” said Bockius. “I just can’t hire enough people to solve that problem. So, I just lived with it and hated that metric.”

Bockius, who hired Capasso for his first sales job, said that using OnProfit’s platform has led to a “10% improvement in that… connection rate, and…that translates into about a 20% increase in revenue down at the end.”

It’s not even 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, SignalFire partner and former New Relic head of growth, said the revenue dilemma was his life for years.  

“Lots of revenue teams are just trying to keep the basics working well, a revenue cycle coming up, an upgrade opportunity tied to a new product release,” said Stoneham, also Stripe’s former CMO. “These seem trivial…but they typically aren’t. You need to get ten people in a room to make anything happen.”

There’s no shortage of potential competitors in the space (essentially everyone applying AI to the revenue and sales stacks). While AI may be the answer, at its core, these are not problems that can be solved solely with tech, said Adam Zeplain, Mark VC cofounder and managing partner. 

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

When I see Capasso, he’s got OnProfit swag that doesn’t feature the company name. Instead, the hat says “Found Money Club.” And that’s intentional. 

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

See you tomorrow,

Allie Garfinkle
X: @agarfinks
Email: alexandra.garfinkle@fortune.com
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VENTURE DEALS

- Protego Biopharma, a San Diego, Calif.-based developer of therapies for protein folding diseases, raised $130 million in Series B funding. Novartis Venture Fund and Forbion led the round and were joined by Omega Funds, Droia Ventures, YK Bioventures, and others.

- Sokin, a London, U.K.-based payments firm, raised $50 million in Series B funding. Prysm Capital led the round and was joined by Watershed Ventures and others. 

- Nevis, a New York City-based developer of AI tools for wealth management firms, raised $35 million in Series A funding from ICONIQ, Sequoia Capital, and Ribbit Capital.

- Tutor Intelligence, a Watertown, Mass.-based provider of AI-powered robot workers, raised $34 million in Series A funding. Union Square Ventures led the round and was joined by others.

- Raindrop, a San Francisco-based monitoring platform for AI agents, raised $15 million in seed funding. Lightspeed Venture Partners led the round and was joined by Figma Ventures, Vercel Ventures, and others.

- Jeeva AI, a San Francisco-based AI-powered platform designed to make sales teams more productive, raised $9 million in funding. JLL Spark led the round and was joined by Sapphire Ventures, Alt Capital, and others.

- Metri Bio, a Boston, Mass.-based developer of therapies for endometrial diseases, raised $5 million in pre-seed funding. Pillar VC led the round and was joined by Pace Ventures and others.

Private Equity

- Stonepeak and Energy Equation Partners acquired a 65% stake in JET, a London, U.K.-based fuel retailer, from Phillips 66 for approximately €2.5 billion ($2.9 billion).

- PayRange, backed by Ridgeview Partners, acquired Kiosoft Technologies, a Boynton Beach, Fla.-based cashless payment platform. Financial terms were not disclosed.

- The Goldman Sachs Group agreed to acquire Innovator Capital Management, a Wheaton, Ill.-based active ETF sponsor. Financial terms were not disclosed.