Over the past few months, a remarkable shift has taken place in the narrative surrounding the future of work. Three CEOs of fast-growing and successful technology companies made statements that, until recently, would have been considered corporate heresy.
First came Jack Dorsey, who announced in February that Block would reduce its workforce by more than 4,000 employees, shrinking from more than 10,000 people to fewer than 6,000. The announcement was particularly striking because it followed immediately after a shareholder letter celebrating strong growth, accelerating product momentum, and increasing profitability.
Dorsey’s explanation was pretty blunt: “Intelligence tools have changed what it means to build and run a company.” He went on to say that he does not believe that his company is early to this realization, but that most companies were late. According to him, within the next year, most companies will reach the same conclusion and make similar structural changes. “I’d rather get there honestly and on our own terms than be forced into it reactively,” he concluded.
A few weeks later, Matthew Prince, CEO of Cloudflare, published an op-ed that may prove to be one of the most important management essays of the AI era. Cloudflare had just laid off more than 20% of its workforce. Again, not because the company was struggling. Quite the opposite. Revenue growth was above 30%, free cash flow was strong, and customer growth was accelerating. “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,” Prince wrote.
Builders, sellers, and measurers
Prince also believes that situations like this will become normal. To explain why, Prince reached back more than seventy years to Peter Drucker’s 1954 classic, The Practice of Management, which divides employees roughly into three groups: Builders, Sellers, and Measurers. Builders are the ones who create the products. Sellers convince customers to buy from them. Measurers are “everyone else”: finance, legal, compliance, operations, audit, HR, middle management, and the countless internal functions that help organizations operate.
Perhaps the most fascinating part about the piece is this: Prince predicts that AI will not come for the builders or the sellers. It will come for the measurers.
The relevance of the builders is easy to understand. As someone who started his career as a programmer, I have always had enormous respect for them. There is something uniquely satisfying about creating, literally making something out of nothing: a blank screen becomes software, and an idea turns into a product.
Prince argues that AI will make builders dramatically more valuable, and his logic is simple. If an engineer becomes ten times more productive, why would you hire fewer engineers? You would probably want more of them. Not because the work disappears, but because the amount of value they can create explodes.
The same is true for sellers. Over the years, I have invested in many startups. Whenever founders ask me what I look for, they often expect answers about intelligence, experience, attitude, technological skills, or work ethic. And, yes, those things matter. For sure. But the ability to sell trumps everything.
A human premium
Glengarry Glen Ross is one of my favorite movies ever, depicting two days in the lives of four real estate salesmen and their increasing desperation when the corporate office sends a motivational trainer with the threat that all but the top two salesmen will be fired within one week. If you haven’t seen it, stop reading this column and go watch it. The cast alone is extraordinary: Al Pacino, Jack Lemmon, Ed Harris, Alan Arkin, Jonathan Pryce, Kevin Spacey, and an unforgettable Alec Baldwin delivering one of the most brutal motivational speeches ever filmed: “ABC. Always Be Closing.” More than about selling, the movie is about persuasion, trust, ambition, and human connection.
And that is why I agree fully with Prince when he writes, “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.” In a world increasingly filled with AI agents, synthetic content, and digital interactions, trust becomes more valuable, not less. The ability to build relationships may even become one of the most important economic skills of the next decade. Perhaps we are even entering an age of a Human Premium; who knows.
So that leaves Drucker’s third category: the measurers. This is where things become complicated.
I spend a surprising amount of my professional life speaking to finance leaders, HR executives, legal teams, auditors, compliance specialists, and operations managers. These are precisely the people Prince places in the category most vulnerable to AI. So, not surprisingly, Cloudflare reduced middle management layers, consolidated operations teams, automated finance functions, and reduced marketing roles. The internal audit moved from examining a handful of risk areas every quarter to continuously monitoring every risk across the organization.
Prince’s argument is difficult to dismiss. AI never sleeps or gets bored, and it can monitor and measure everything simultaneously, with a level of detail that was previously impossible. Drucker would have loved it.
Ark Fleet Ship B
And yet, reading his essay, I could not stop thinking about Douglas Adams’ Ark Fleet Ship B.
In The Hitchhiker’s Guide to the Galaxy, the inhabitants of the planet Golgafrincham came to believe that a large segment of their population served no useful purpose. To solve the problem, they loaded these supposedly expendable citizens onto a giant spacecraft known as Ark Fleet Ship B. Among the passengers were telephone sanitizers, account executives, management consultants, personnel officers, public relations specialists, security guards, and countless other intermediaries. Meanwhile, those considered truly valuable remained behind: the thinkers, the leaders, and the people who actually got things done.
What happened next is one of Douglas Adams’ greatest jokes. The people on Ship B eventually crash-landed on Earth and became our ancestors. Even more ironically, the people left behind on Golgafrincham all died after contracting a disease from a dirty telephone.
It proves that Adams understood something profound. Many of the functions we dismiss as bureaucratic only reveal their value when they disappear. Frederik Anseel beautifully described this phenomenon in an earlier newsletter edition, saying that we often assume that when something becomes automated, it simply disappears. But human systems tend to be functionally layered. He offered the example of universities: “With AI, you might think: ‘The core of a university is knowledge and information, and if AI makes knowledge abundant and free, then universities lose their purpose.’ But that logic misses an important point. A university isn’t just about transferring knowledge. It’s also a selection mechanism, a status signal, a certification system, a social connector, and a community that gives people identity and belonging.” The exact same things can be said about job functions, which have a top functional layer that is obvious to all, but many less visible layers that will only manifest themselves when they are gone.
A radically AI-native operating model
Which brings me to a third announcement. A few days ago, ClickUp CEO Zeb Evans announced that he was laying off 22% of his workforce while simultaneously introducing what he called a radically AI-native operating model. The company has reportedly deployed thousands of internal AI agents to perform increasingly complex work. Evans believes this will eventually create a “100x organization.” His most provocative statement was that employees capable of generating extraordinary impact with AI may earn salaries exceeding one million dollars per year.
He imagines a future in which smaller organizations deploy thousands of AI agents to perform tasks that once required large teams, while a small number of exceptionally productive individuals orchestrate the entire system. Individuals whom Cloudflare’s Matthew Prince believes will be builders and sellers.
Maybe. But I am not convinced the future belongs exclusively to builders and sellers while measurers disappear. What I suspect instead is that all three categories are beginning to merge. The best finance professionals will build. The best HR leaders will orchestrate AI systems. The best compliance officers will automate entire workflows. The best operations managers will become architects of intelligence. The best measurers will not be replaced by AI but become amplified by it. Perhaps dramatically so. Perhaps even enough to justify a million-dollar salary.
Don’t be late
The most important lesson from Prince, Dorsey, and Evans is not that AI is eliminating jobs. It is that AI is eliminating excuses to transform organizations faster than ever. Bureaucracy, hierarchy, and organizational complexity can no longer shield against accountability.
The future may belong neither to the builder, nor the seller, nor the measurer. It may belong to those capable of rethinking all three. Because history has a funny way of reminding us that the people we think are useless sometimes turn out to be the ones keeping the whole system alive. And those companies that understand that are probably not too early. It may be that everyone else is late.
The article originally appeared on LinkedIn.