Jack Dorsey to Middle Managers: AI Will Do Your Job Better (and Cheaper)

Block co-founder Jack Dorsey has dropped his vision for the future workplace: AI as your boss. Yep, the same guy who nuked 40% of Block's headcount in February is now suggesting we ditch middle management entirely and let algorithms handle the micromanaging. Move fast, break things, replace middle managers with prompt engineering—very on brand for a Bitcoin maximalist.

In a blog post with Block's lead independent director Roelof Botha, Dorsey argued that AI can track projects, spot problems, assign tasks, and share critical info faster than any human manager could. Block is apparently in the "early stages" of building what they call "a company built as an intelligence, or mini-AGI." That's right, Skynet but for payments. Hope you like having your PTO requests processed by a language model.

"We're questioning the underlying assumption: that organizations have to be hierarchically organized with humans as the coordination mechanism," they wrote. "Instead, we intend to replace what the hierarchy does." Imagine explaining to your manager that the algorithm has decided your department is redundant. Gaslight, gatekeep, replace with LLM.

To be fair, most companies using AI today are just giving everyone a copilot—making the existing structure work slightly better without changing it. It's like putting a turbocharger on a horse and calling it a revolution. But Dorsey and Botha want something different: a company run by machines, with humans playing supporting roles. Think of it as a DAO, but instead of rugging the community, the smart contract just optimizes you out of a job.

The timing is, let's say, interesting. Block slashed roughly 4,000 jobs in February, with Dorsey pointing to AI's rapid acceleration at the company as the reason. Some of those laid-off workers were quietly brought back in March, so it's not entirely doom and gloom for humans. Nothing says "we believe in human potential" like a hiring freeze that lasts until Q2.

Dorsey and Botha still see people in key roles—just reorganized. Workers would fall into three categories: "individual contributors" who build and maintain operating systems, "directly responsible individuals" tasked with solving specific problems using whatever resources they need, and "player-coaches" who mentor others while still writing code. Basically: the ones doing the work, the ones holding the bag when things go wrong, and the ones pretending they still have work-life balance.

The duo argued that traditional hierarchies are too slow. Information flows from workers to managers to executives and back down—a process they say AI could streamline dramatically. It's like comparing a Bitcoin transaction to a wire transfer. One has