The Art of the Inevitable: Why I Stopped Underwriting Product-Market Fit

By Lisa Calhoun, Founder & Managing Partner, Valor Ventures

Every week I learn from driven founders showing me the art of the possible. They're living in a future, and I never get tired of going there with them. Generally, when I take an intro meeting with a founder, I already believe them — it is possible. That's exactly the problem. In this market, possibility is table stakes.

What I'm learning to underwrite now is the art of the inevitable — the thing whose time has come. I've written before on this blog that I believe distribution is the new moat, but that statement, while somewhat challenging for most at the time, didn't take it far enough. I have to say something slightly more heretical: I think product-market fit, as we were all taught it, is dead.

Fit assumes there's a fixed market. That's so 2022.

The classic PMF doctrine — build, iterate, listen, converge on fit — assumes the market is a relatively fixed target you can tune into. For SaaS, it was true. The access to intelligence via AI has broken that completely. The customer is now changing as fast as, or faster than, the startup, and is a dynamic canvas clinging to capital flows. AI is transforming the enterprise buyer twice at once: once at the level of the individual employee, and again at the level of the enterprise itself.

Your buyer is mutating faster than your roadmap

There's not a lot of research I can share on this, it's mostly my lived experience day in and day out. But I did give finding you some anchors a good try.

St. Louis Fed: within roughly two years of launch, nearly 40% of U.S. adults (18–64) were using generative AI — versus about 20% adoption for the personal computer three years in. The fastest technology diffusion ever measured, happening inside your customer's workforce whether their IT department planned for it or not.
Menlo Ventures: enterprise AI spend went from $11.5B in 2024 to $37B in 2025 — 3.2x in a single year — while the build-vs-buy preference flipped from 47% build to 76% buy in twelve months.
a16z's survey of 100 enterprise buyers, one CIO: "What I spent in 2023 I now spend in a week." I'm seeing this live across our region.

You can't converge on a moving target. You can only move with it — I think of it as adaptive fit. And the companies proving they can move with it aren't winning on product. They're winning on distribution.

What inevitable looks like up close

I'm sure I'm not the first VC who's wanted the founder to prove something is inevitable. How could you even do that? The companies I've underwritten in the last year all have elements of it.

UpDraft is a complex accounting system that came out of a deeply networked operator, PricewaterhouseCoopers alum Tim LaBelle, who lived the problem as a trusted managing director working for over 100 major accounts. From his earliest customers, he's reached into the top echelons of the global accounting infrastructure.
EasyAudit, the compliance infrastructure for serious businesses, didn't spring from a great idea to evolve product market fit. The founder, Christian Khoury, had lived with the problem as a compliance leader at Deloitte. Finding multi-billion dollar customers wasn't a new move — it was the move.
Evrim's depth in global economic intelligence from hard-to-find Chinese, Latin American, and Middle Eastern sources wasn't a great idea that could iterate its way into operation. The founders had defense clearances and a decade of experience in technical solutions with Thomson Reuters Special Ops. The distribution advantage came with the prompts, not after.

One had Epic.

It's not just Valor's portfolio, either. You can see more mature examples of winners going to market with out-positioning, especially via distribution. Abridge became the first ambient AI tool officially integrated into Epic's EHR through Epic's Pal program — which handed it preferential access to the 38% of U.S. hospital networks running Epic, and put it 3–6 months ahead of every competitor on integration depth. The result: $100M ARR by May 2025, Kaiser, Mayo, Hopkins and UPMC on the logo wall, and a valuation that ran from $2.75B to $5.3B in four months. Plenty of ambient scribes had comparable products — I've seen over a dozen of them pitch Valor. One had Epic.

Another quick example. Sierra went from $26M ARR at the end of 2024 to $200M by May 2026, and now works with 40% of the Fortune 50. Is that because Sierra's agents are categorically better? Pardon my doubts there, but I do doubt it. I think it's because Bret Taylor — former Salesforce co-CEO, current OpenAI chairman — has uncommon access to the top decision-makers of every large enterprise on the planet, major equity, and something to prove. That's not a go-to-market strategy. That's a person who can do distribution. When I say I underwrite the inevitable, this is what I mean: a team member whose Rolodex is the sales pipeline.

The C-suite is the new landing page

I'm paying keen attention to how deals get done today, and it's changing.

The bottoms-up, PLG-era canon of 2019–2021 said the buyer was the end user and the executive was the last to know.

With AI making every executive do the work of 20, and hollowing out middle management, that's inverted now. In a16z's data, AI innovation budgets collapsed from 25% to just 7% of LLM spend in a year — not because spend fell, but because AI moved into permanent IT and business-unit line items, owned by executives, mandated from the board down. Employees still discover the tools (Menlo found 27% of AI application spend arrives via PLG, ~4x traditional software) — but the contracts that matter are signed in the C-suite, faster than ever: 47% of enterprise AI deals reach production, nearly double the 25% rate of traditional SaaS.

Underwriting trillions, casually

For an investor, the market is doing its best to talk us out of price or round discipline. Pricing, as Samir Kaji has been documenting, has gotten unmoored — people are casually underwriting trillion-dollar outcomes. Founder Collective's research, discussed on Kaji's Venture Unlocked, looked at 25 years of the top 500 venture exits and found the median was roughly $2.7 billion.

We're seeing this movie in private equity, too. Chase the peak of the wave, pay for perfection, and hold when the exit window doesn't cooperate: at the end of 2025, per PitchBook, roughly 40% of PE-backed companies in the U.S. — more than $860 billion in net asset value — had been held for more than seven years, the highest level since 2016 and the third straight annual increase. That's what "possible, priced as certain" looks like a decade later. We're still waiting on realizations there.

The questions that replaced "could this work?"

So the question I ask in pitch meetings has changed. Not "could this work?" — almost everything in front of me could work. The questions are:

Who has to say yes for this to become inevitable — and do you already know them? Not "we'll hire enterprise sales." The last founder I underwrote showed me a key account list — with email addresses and discussions of last meetings.
What distribution agreement makes the market come to you? The Epic Pal, the platform marketplace, the channel partner with quota-carrying reps — there are contracts that convert someone else's (dynamically eroding) install base into your pipeline.
Who on the cap table has major equity, a chip on their shoulder, and access to the top ten decision-makers in the category? Because in a market where the buyer reinvents itself every year, the only durable fit is with the people, not the spec sheet.

The art of the possible gets you a meeting. The art of the inevitable gets you a term sheet — at least at Valor. I hope this helps.

Your move

Think product-market fit isn't dead — or think you're building the inevitable I should see next? Both conversations start the same way: show me the deck. Valor gives real analysis of your deck, from a fund that leads first rounds.

Share your deck with Valor → DeckCheck

— Lisa

Lisa Calhoun is Founder and Managing Partner of Valor Ventures, an Atlanta-based seed fund backing AI-augmented founders building the South's next generation of category leaders.