The Orchestrator

In February 2026, Block cut roughly four thousand jobs — about forty percent of its workforce — and CEO Jack Dorsey tied the decision to AI productivity. Block followed with the essay Chapter 1 described, “From Hierarchy to Intelligence,” arguing that most companies give everyone a copilot to make the existing structure slightly better, while Block claims to be after a different structure.¹ Block also built Goose, the open-source agent discussed earlier in this book, as part of that bet.

Whether those cuts were mostly about AI or mostly a correction for prior over-hiring is contested, and analysts said so at the time. The organizational thesis still matters here regardless, because a company that installs assistants into the old org chart is doing one thing while a company that redesigns coordination around systems that can act is doing another. Orchestration is the second project, and headcount theater that pretends the first project is the second belongs in the failure chapter rather than this one.