Cloudflare CEO Matthew Prince’s op-ed: “How I choose which Cloudflare employees to replace with AI”

Matthew Prince, the chief executive of Cloudflare, has spent months defending almost every sentence he wrote about his company’s AI-driven layoffs. The one line he keeps at arm’s length is the headline, which happens to be the most honest sentence of the lot.

“How I choose which Cloudflare employees to replace with AI.”

That was the title The Wall Street Journal ran over Prince’s op-ed in May, shortly after Cloudflare cut 1,100 jobs, roughly 20 percent of its staff. When Nilay Patel read it back to him on The Verge’s Decoder podcast, Prince pushed back: “I didn’t get to choose the title, because again, the way media works today is they create the titles, but yes, but I wrote the rest of it.”

The rest of it is a rubric for choosing

The rest of it is a method. Borrowing from Peter Drucker, Prince sorted the company into builders, sellers and measurers. Builders and sellers stay, and Cloudflare says it wants to hire as many as it can. Measurers were the majority of those let go: internal audit, finance, legal, revenue recognition and a layer of middle management. “AI isn’t coming for builders or sellers, but it is coming for measurers,” he wrote.

His examples are specific. An investor-relations team of about 20 people used to spend two weeks assembling earnings documents; Cloudflare cut that to three minutes. Managers who once averaged six direct reports now run up to 12, which flattened the org chart and, by Prince’s account, exposed a tier of middle managers who “just weren’t the right folks.” The company also trained models on its known high performers and ran them across the workforce to surface rising stars, conceding that “there were some mistakes.”

Each of those is a decision about who stays. The headline Prince disowns simply says so out loud.

Not a company in trouble

What makes the case unusual is the balance sheet. “I didn’t do it because Cloudflare is struggling,” Prince wrote, and the numbers support him: first-quarter revenue of $639.8 million, ahead of analyst estimates and more than 30 percent up on the year. That makes the lazy reading, a weak company dressing up cuts as strategy, hard to sustain. Skeptics have a sharper suspicion. Marc Andreessen, quoted by Fortune, put it bluntly: “Now they all have the silver bullet excuse: Ah, it’s AI.”

Prince’s answer is that the reshuffle is coming for every industry and that moving first is the kinder option, because it is easier to find a new job before everyone else reaches the same conclusion. He also described what going early cost him: a sliding share price and death threats “from just random people who are anti-AI.” His word for peers who hesitate is blunter than anything the Journal printed. The quotable half reads: “If you’re a real leader, get out there and actually do the work.”

The founder who argues in public

None of this is out of character. Prince has a long habit of agonizing over Cloudflare’s power in print and then acting on it, most famously when the company cut off the neo-Nazi site Stormfront. He writes his hardest decisions out, signs them and takes the questions. That is why the quibble over the title stands out. A CEO who narrates every step of a restructuring objects only to the sentence that names who does the selecting.

And the selecting has not been handed to a machine. Prince draws that line himself: “If every promotion decision is made by some totally unaccountable AI system, that seems wrong.” The tools measure; the chief executive decides. What AI has changed at Cloudflare is where the measuring happens. It has moved from a department of people to a set of models that report upward, which concentrates the choice instead of dissolving it.

Cloudflare now employs somewhere between 4,500 and 5,000 people, and Prince expects that number to grow again, heavy on builders and sellers. The measurers are not coming back. Their work now runs through systems that answer to Prince, which makes the Journal’s editors more accurate than he would like. Someone does choose. It is him.

Tags: layoffs, Cloudflare, Matthew Prince, Middle managers, The Wall Street Journal