When he is not talking about replacing middle managers with AI, billionaire Jack Dorsey is often talking up Bitcoin. (Photo by Marco BELLO / AFP) (Photo by MARCO BELLO/AFP via Getty Images)
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Billionaire Jack Dorsey cut first and explained later.
In February, Block, the financial technology company behind Square and Cash App, said it would lay off more than 4,000 people, about 40% of its workforce. Investors loved it. Shares jumped as much as 24% in extended trading. The payments company, which had $24 billion in revenue in 2025, said smaller teams and more artificial intelligence would help it move faster.
On Tuesday, Dorsey explained what he thinks those smaller teams may actually look like. In a blog post coauthored with former Sequoia managing partner Roelof Botha, he argued that AI could do much of what middle managers do today. Sequoia, with more than $50 billion of assets under management, is one of Silicon Valley’s most important venture capital firms. It backed companies like Google, Apple, Nvidia and Airbnb early. About 21 million Americans work in management occupations, according to the Bureau of Labor Statistics. That comes out to roughly 12% of the workforce. Dorsey and Botha are arguing that companies may not need as many of them in the future.
Most companies are built like pyramids. Information moves up from workers to managers to executives, then decisions come back down. Managers gather updates, pass along instructions, coordinate projects and keep teams aligned.
Dorsey and Botha argue that AI can now do much of that work now.
They compare modern companies to the Roman army. Roman leaders had to manage legions of soldiers spread across large distances. The answer was layers of command. One person managed a smaller group of people. Then another person managed those managers. Big companies still work the same way.
The difference, they argue, is that software can now track projects, spot problems, route work and share information faster than humans can. At a remote-first company like Block, where meetings, code changes, plans and messages are all recorded digitally, AI can build what Dorsey and Botha call a “world model” of the company. In plain English, that means AI can keep an always-updated map of what is happening inside the business.
The same goes for customers. Block sees millions of payments through Square and Cash App every day. Dorsey and Botha say that gives the company a real-time picture of what customers and merchants need. Instead of waiting for managers to pull reports and make decisions, AI could step in sooner.
Markets like the idea. Block’s shares rose about 3% after Dorsey and Botha published the paper. Investors generally reward companies that promise to cut costs and move faster because lower costs typically translate to higher earnings per share.
Still, there are reasons to be skeptical. Block isn’t operating from a position of strength. Outside of a brief post pandemic-era surge, its stock has mostly gone nowhere for the last decade. A company under pressure is often more willing to try something radical.
But Dorsey is probably right about one thing. If this works at Block, other companies will follow. Botha’s involvement makes that more likely. He spent years backing Silicon Valley’s biggest winners. If he thinks flatter companies powered by AI are coming, other executives will pay attention. And a lot of middle managers may soon be left trying to figure out where they fit in a large language model world.
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Source: https://www.forbes.com/sites/brandonkochkodin/2026/03/31/billionaire-jack-dorsey-thinks-ai-will-kill-middle-management/
