Standard diligence covers the financials, the legal, the tech, and the competitive position. It doesn't assess the state of the category belief — and whether the company you're pricing is on the right side of it. In B2B SaaS, that gap is where the multiple lives or dies. Here is what it costs — and what closing it produces.
I joined Piano in 2016 wary. They had a product for an industry that had struggled for twenty-five years — ever since the internet made information free. Publishers had been losing the battle that long. Many had stopped believing they could win it.
My job was to build a global and elite customer success team that could retain and grow the accounts. It became immediately clear to me that if we relied on each publisher to figure out how to build a new direct revenue stream on their own, most wouldn't be able to do it, and we would lose most of them. So I decided I had better figure it out and share the knowledge with all of them so they would succeed and grow with us.
I spoke with everyone at Piano who had come from the industry. Asked everything. Eventually something became clear: publishers knew their content was largely commoditized, but they kept trying to monetize it anyway. It made no sense. So I asked a different question. If content isn't the valuable asset — what is? The answer was their loyal audience. People who visited daily, spent time with them, loved being associated with them. People who would buy something, if it was worth buying.
I'd start by listening to them, all the trials and tribulations. They were desperate for an answer. And every time I delivered it, the response was the same. Not "what features does your product have?" or "what's the price?" Just: "How? How do we do that?" Eager and relieved.
That's when I knew we were no longer in a product conversation. We were solving their most critical business challenge — and from that moment, there was no competition. A deal in Spain that should have renewed at $80K became a four-year, $1M partnership. A deal in Ukraine closed at $750K in a market where the average contract had been $30K. The product didn't change. The conversation did.
A standard diligence process validates four workstreams. Each is rigorous within its lane. None asks the question that determines the multiple.
These questions don't replace the four standard workstreams. They complete them. Each one connects directly to valuation — ceiling, mispricing, compounding.
The founding belief — revenue predictability is a data and visibility problem — has been dominant for thirty-two years. Fewer than 20% of sales leaders rate their forecast accuracy as predictable after full category adoption. The median hasn't moved. The category has been solving the wrong layer of the problem with increasing precision.
Agentic AI is now attacking the business model of every company inside it — seat compression, interface bypass, and commoditization from below simultaneously eroding the moats incumbents built over twenty years. The incumbent response is to integrate agents into existing products. That is the wrong race: agents executing a mis-scoped belief faster still produce the wrong answer, just more efficiently. The two largest players are consumed by integration for 18–24 months. Nobody is watching the door that just opened.
The full analysis is in The Example — the category, the vendor landscape, the real problem named, and a specific read on People.ai: current ceiling, available conversation, and the questions the management presentation needs to answer.