Jack Dorsey Declares War on the Middle Manager: AI's Got the Keys Now

Jack Dorsey just pulled off what every tech CEO secretly dreams about — cutting roughly 4,000 employees while calling it something other than layoffs. In his new essay "From Hierarchy to Intelligence," co-authored with Sequoia Capital's Roelof Botha, Dorsey argues Block's mass departure wasn't about saving cash. It was a permanent restructuring to replace middle managers with artificial intelligence. The man who once made us all carry tiny computers in our pockets is now trying to make us obsolete. Bold strategy, Cotton.

The timing? Dorsey says he noticed a capability shift in December when Anthropic's Opus 4.6 and OpenAI's Codex 5.3 showed they could actually handle large codebases without falling apart. That was all the proof he needed. Suddenly the machines weren't just writing haikus about sandwiches — they were touching production code and living to tell about it. Dorsey saw the writing on the wall and apparently decided to help it along.

The logic goes something like this: corporate hierarchies exist because organizations got too big for one person to manage. Someone had to route information up and down the chain. Managers aggregated context, played messenger, and kept teams aligned. Now AI can do all that continuously and at scale. The messenger, according to Dorsey, is obsolete. It's giving "your manager is a middleman" energy, and honestly? Some of us in the crypto space have been saying this about traditional finance for years. Now Dorsey's applying it internally. The irony of a former Twitter chief executing a hostile takeover on middle management isn't lost on anyone.

So what's replacing the management layers? Two AI-driven "