AI is causing job losses in all sorts of companies, but these losses aren’t uniform across functions.
That’s the core argument from Matthew Prince, CEO of Cloudflare, who recently laid off more than 20% of his workforce — 1,100 employees — despite the company posting record revenue growth, strong free cash flow, and adding customers at an unprecedented rate. The cuts were deliberate and structural, not a sign of distress. And Prince wants the business world to understand exactly who AI is coming for.
A Framework From 1954
To explain his thinking, Prince reached back to Peter Drucker’s The Practice of Management, published in 1954. Drucker mapped the different roles inside every business, which Prince distills into three categories: builders, sellers, and measurers.
Builders create products. Sellers sell those products. Measurers do everything else: internal audit, revenue recognition, finance, legal, compliance, middle management, operations, and on and on.
The distinction matters because AI doesn’t threaten all three equally.
Who’s Safe — And Who Isn’t
Prince is unambiguous about builders: “Contrary to what some analysts predict, builders aren’t going anywhere. If an engineer on my team can now be 10 times as productive, I’m going to hire as many as I can find.” A more productive engineer isn’t a displaced one — it’s an argument to hire more of them.
Sellers are safe too. “Humans still control budgets, and they want to buy from people who take the time to understand their needs, build trust and fix whatever goes wrong.” Sales is fundamentally a relationship function, and Prince sees no AI replacement on the horizon.
Measurers are a different story. Prince argues they are critical — but unlike builders and sellers, their work is now highly automatable. “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.”
What This Looked Like At Cloudflare
The Cloudflare layoffs were a direct application of this framework. “The vast majority of those we laid off last week were measurers.” Middle managers were cut across the organization because AI allows for more direct reports per manager while still measuring and mentoring teams effectively. Operations functions were consolidated into a single group that can draw on AI for specific expertise when needed. Marketing was significantly reduced — which, as Prince notes, “like in most companies, was teeming with measurers.” Across the finance team, the company found opportunities to consolidate and automate.
For Cloudflare internally, AI has already transformed the audit function. “Internal audit previously picked a handful of business risk areas to scrutinize each quarter. Now we’re moving to a system in which every business risk is audited continuously.” The company is closing books faster, making fewer errors, and catching the ones it does make more reliably.
Not A Headcount Play
The counterintuitive part of Prince’s message: Cloudflare has a record number of open positions. This wasn’t about getting smaller. “In coming years I expect our number of employees will continue to grow. With fewer people needed for measuring, we can now invest more in people in the areas that drive growth.”
Nearly a million people applied for 1,111 paid internships at Cloudflare this past summer. Every intern hired was AI-native, and all of them were builders or sellers. Prince expects the majority to receive full-time offers.
This pattern — cutting measurers to fund builders and sellers — is likely to spread. Prince is explicit: “We haven’t found another example in U.S. business history of a public company growing at more than 30% that laid off more than 20% of its workforce. Yet what we did is likely going to become the norm over the next year.”
The Broader Picture
Prince’s framework gives sharper definition to a trend that’s been unfolding across the industry. Coinbase cut 14% of its workforce and is restructuring toward AI-agent-driven operations, flattening management layers and eliminating pure management roles. Intuit laid off 3,000 employees while doubling down on AI — a company whose core products sit squarely in finance and accounting, the archetypal measurer territory. Upwork cut 25% of its workforce citing AI-powered smaller teams. Finance job openings have already fallen to their lowest level since the 2008 financial crisis — not because companies are struggling, but because they need fewer people to do the same work.
The “measurer” label explains a lot of those cuts better than the vague “AI efficiency” language most CEOs deploy. Audit, compliance, middle management, finance operations, marketing analytics — these are all measurer functions, and they’re the ones being hollowed out first.
What It Means Going Forward
Prince’s conclusion is deliberately optimistic about the next generation: “AI isn’t the harbinger of bleak youth unemployment — it is quite the opposite.” His argument is that AI will finally let companies accurately measure individual contributions and identify future leaders — something that was always hard to do in organizations padded with measurement overhead.
The framing is direct: “AI won’t kill all jobs. But it will change every business. Ultimately, it will prove Drucker right. AI will allow us to better measure our organizations so the humans on our teams can focus on where they create and capture value: building and selling.”
For anyone in a measurement-heavy function — finance, compliance, middle management, operations — this is the clearest signal yet of where AI’s first wave is landing. Cloudflare moved first, and visibly. Others are moving too, just more quietly.