Is Product Market Fit Getting Harder to KEEP?

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There are a ton of pieces written about finding product-market fit—what it feels like both quantitatively (customer retention) and qualitatively (people yanking the product out of your hands before it’s truly ready).

But what I want to talk about is keeping product-market fit.

And I don’t think I’m out of line in saying it’s gotten a hell of a lot harder.

Harry Stebbings had a great episode of 20 Minute VC, where he, , and Rory O’Driscoll discussed companies falling in and out of PMF.

Jason said that once upon a time, if you hit PMF and had a decent team, you were golden for about five years.

Around year three, you’d start incubating a new product to jump the S-curve and extend your growth runway. Add a new product. Expand to a new geo. You know the playbook.

What we’re seeing now is AI companies obliterating classic timelines—hitting $50M, $100M, even $200M in revenue within a couple of calendar years.

It looks kinda like this:

BUT… we’re also seeing companies lose PMF just as fast.

Rory noted he’s seeing companies fall in and out of PMF three times in two years. What used to be a five-year moat can vanish in five weeks.

And what really breaks my brain? A lot of these companies haven’t even been around long enough to test the physics of enterprise renewal cycles. The curve might actually look more like this:

This all got me thinking about “escape velocity.” That old triple-triple-double-double path to $100M? It used to earn you the right to become the incumbent.

But these days, it’s harder to know if someone’s really hit escape velocity—or if they just caught a tailwind. touches on this in an excellent Clouded Judgement Piece.

I run a lot of road races in my spare time. And it kinda reminds me of a “false peak.”

Here’s an elevation map from one I did last year. Around mile 6.5, when you’re already gassed, you push hard to get over a massive hill… only to discover there’s another hill from mile 7 to 7.5.

You thought you were done.

You were not done.

That’s what it feels like to chase PMF in 2025. You think you’ve made it—only to discover another climb, or worse, a valley in between.

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Employment Hero is one of Australia’s top tech breakouts. We spoke to their CFO Rob Patterson. Things we covered: