We’re kicking off our Founder Series on Between Two Quarters with Charley Dehoney, Co-Founder & CEO of Upwell—nvp capital’s first native GenAI investment (early 2023). In this episode, Charley and I dig into his 20+ year journey in logistics, the working-capital pain that sparked Upwell, and what it really takes to commercialize AI software for the enterprise. 

Here are some key takeaways from our conversation:

• The problem picked him. Years running trucking brokerages taught Charley that you can move freight flawlessly—but a single invoice error (missing PO, routing code, or document) can freeze payment and crush cash flow. The real squeeze sits between accounts payable and accounts receivable terms: carriers want net-15; shippers push 30–90 days. Upwell exists to close that gap.
• GenAI unlocked the “judgment” step. APIs/OCR/RPA weren’t the blockers—decisioning was. Foundation models now let Upwell read documents, map each shipper’s payment standards, and flag invoice exceptions before they’re sent—keeping dollars out of exception limbo and in the bank.
• Nail one wedge; don’t boil the ocean. Early interest isn’t a product. Upwell resisted doing “a little of everything” and shipped a focused set of high-need workflows where value is unmistakable.
• Enterprise sales is a contact sport. Meet big companies where they are (yes, on Teams), follow up impeccably, and send call notes same day. Your champion is fighting internal inertia—help them look great.
• It’s not a pilot—it’s a proof of concept. Define one use case, lock baselines up front, measure, and broadcast results so your sponsor earns political capital. Align your impact to their career outcomes.

The founder reality

Charley learned cash-flow pain the hard way. Early on, AR delays piled up, invoice exceptions stalled payments, and reserves dwindled—culminating in a Thursday when he sold his car for cash to make payroll. It was a gut-check moment that clarified the real problem: if invoicing isn’t right and cash doesn’t arrive on time, the whole operation grinds to a halt. Along the way, his wife—an ex–software seller with a finance brain—stepped into the business and made the numbers impossible to ignore: AP vs. AR, burn vs. runway, what had to change. Her belief that the problem was solvable—and that Charley should be the one to solve it—helped push the idea from “this hurts” to “this has to exist,” shaping the company Upwell would become.

From idea to first customers

Charley later saw the same AR chaos at scale inside global enterprises—solved with offshore BPOs, latency, and error-prone handoffs. Two forces converged in 2022: a named Order-to-Cash category (Gartner) and the ChatGPT moment, which made automated judgment calls viable. With CTO Aaron (an AI vet), Upwell started aggregating a catalog of shipper payment rules and used LLMs to interrogate each invoice: Is the PO present? Is the routing code right? Do the docs match the standard? Catch exceptions pre-submission, keep cash predictable.

By late 2023, Upwell was demoing aggressively, refining its first use cases, and winning early adopters. Working closely with those customers did more than validate the concept — it confirmed that Upwell had moved from nice-to-have to need-to-have.

Seeking more founders like Charley

Charley’s journey captures what it really takes to build in the enterprise trenches — and why we back founders who’ve lived the pain they’re solving. His lessons are universal: validate before you brand, ship focus, and run the enterprise playbook with persistence and precision. Charley’s path from payroll panic to building and validation a platform shows that conviction and clarity beat hype every time.

That’s the kind of founder we love to back at nvp capital — operators who turn firsthand pain into generational products.

Watch the full conversation below to hear Charley’s full story: