Frameworks, core principles and top case studies for SaaS pricing, learnt and refined over 28+ years of SaaS-monetization experience.
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The SaaSPocalypse of early 2026 is not a correction. It is a prelude. Roughly $2 trillion in software market value erased over twelve months, a full trillion of it between mid-January and mid-February alone. SaaS multiples compressed below those of the broader market for the first time in the history of the sector. Orlando Bravo, the most prominent software investor in the world, calling some of the declines "very warranted."
Workday down nearly half over the same stretch. Salesforce, Adobe, ServiceNow, Monday.com, and Atlassian all taking real hits as enterprise customers began questioning their seat assumptions. These are not signs of a temporary dip you can wait out. They are the market telling you, in the most expensive language it knows, that your business model is structurally impaired.
The reason is simple, and it is the same reason McCabe moved so fast: when your AI agent makes your product so effective that customers need fewer seats, your product's success destroys your revenue. It is arithmetic.
And while you are watching your seat counts erode, AI native companies are building the replacement from scratch. It is a rebuild we watch up close at Monetizely. Sierra, founded by Bret Taylor and Clay Bavor in 2023, launched publicly in February 2024. In May 2026 it raised a $950 million Series E at a $15.8 billion valuation.
Sierra charges purely on outcomes: you pay when the AI resolves the customer's problem, and you do not pay when it does not. They never had to transform away from a seat model because they never had one.
McCabe framed it as a civilizational shift, not a software cycle.
His own words: "The story of digital technology is really short and it's punctuated by a small number of things. Microprocessors, personal computers, the internet, maybe mobile. Now there's AI. I think AI is bigger than all these things. And all of these things disrupted all categories. So not only is this likely to disrupt all the categories, it's going to disrupt in the most aggressive, violent ways. And if you're not in it, you're about to get kicked out of all of it."
This is why the hail mary is no longer the aggressive play. It is the default play. The "prudent" approach, the one built on waiting, studying, piloting, and forming a committee, is the one that kills you.
Join companies like Zoom, DocuSign, and Twilio using our systematic pricing approach to increase revenue by 12-40% year-over-year.