Cloudflare's CEO Prince just published an Op-Ed in the Wall Street Journal titled "How I Choose Which Cloudflare Employees to Replace With AI." In it, Mr. Prince invokes Peter Drucker's people buckets of "Builders, Sellers and Measurers" and argues AI is replacing Measurers:
AI isn't coming for builders or sellers, but it is coming for measurers. Tireless, independent, efficient and available, AI systems can now measure an organization with a level of objective detail and precision that was previously impossible even for the best employees.
Here's the thing: that's bullshit. How do I know? By asking a simple question: "Who benefits from this?" Cutting 20% of headcount at a company posting record revenue growth and strong free cash flow is one of the most reliable ways to expand operating margins, lower the expense base, and trigger a stock re-rating. It's a pure-play shareholder value move. It's blatant financial engineering for the cap table. The AI framing is just a cover story told so shareholders don't notice you might have overspent, overhired, and underdelivered in the past. A quick look at Cloudflare's recent numbers reveals their margin is actually under pressure because of higher infrastructure costs. Put another way, their AI efforts probably turned out to be very costly and didn't lead to additional revenue - so they had to cut staff. Wow, what a banger. And by the way: choosing the form of an Op-Ed in the Wall Street Journal, with medium and message going hand in hand, really gave it away.
Don't get me wrong. I don't think the AI argument is necessarily wrong - more on that in a bit. But a CEO's personal compensation is either directly or indirectly tied to the stock price. When a major restructuring announcement creates exactly the conditions for stock appreciation, the burden of proof shifts. You need more than a 70-year-old Drucker taxonomy and some enthusiasm about continuous auditing to make the case that this was a principled AI bet rather than a margin optimization dressed up as a philosophical statement.
The people who lost their jobs deserve a clearer accounting than "the future is builders and sellers." Especially when the person delivering that message probably had a six- to seven-figure financial reason to deliver it on the front page of the Wall Street Journal.
Now, let me come back to the AI argument. I actually believe the Cloudflare CEO's AI argument is real - but it doesn't go far enough. He says: AI makes each engineer vastly more productive, so builders are safe. But the logic runs the other way. If a single engineer can do the work of ten, the economically rational move is to employ one-tenth the headcount and capture the margin. "I'll hire as many as I can find" is the answer a CEO gives when they haven't followed their own reasoning to its conclusion. Because if you only had 10x Builders on your team, you would produce 10x the output - but never 10x the outcome. You would lose focus, spread yourself thin on too many fronts, and get whacked on Wall Street.
The reason builders feel safe today is that the 10x productivity claim is still aspirational for most organizations. The tooling exists; the management systems, hiring structures, and org designs haven't caught up. But they will. And when they do, the same reasoning used to eliminate measurers applies with equal force to builders: if AI can do this better, faster, and cheaper, the number of humans required drops.
I fear the builder/seller safe harbor might just be a lag, not a guarantee. Organizations are still figuring out how to restructure around AI-amplified engineering. Once they do, the headcount math becomes uncomfortable in exactly the same way it became uncomfortable for finance, compliance, and middle management. The people reading today's narrative as a permanent forecast are mistaking the direction of travel for the destination. The only category that seems truly safe is the one writing the WSJ op-eds about which categories are safe.
Thoughts? Find me on Bluesky.