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The middle manager Jack Dorsey wants to eliminate is you.
Block's CEO posted in April that there's "no need for a permanent middle management layer," and said he was compressing his org from five reporting tiers down to two or three. Meta's Reality Labs swapped traditional supervisor titles for "AI builder," "pod lead," and "org lead." Atlassian announced 1,600 layoffs in January with 900 cuts coming from research and development, framed as an AI pivot, despite Mike Cannon-Brookes telling 20VC five months earlier that the company would employ more engineers in five years. Salesforce cut 4,000 customer support roles and replaced them with AI agents, dropping that group's headcount from 9,000 to 5,000. Workday gutted Global Customer Operations.
The story has a name. Press is calling it the Great Flattening. Analysts at Gartner project that one in five firms will use AI to compress their middle management ranks by the end of 2026.
You are a founder running 22 people at $3M ARR. You read all of this. You start to think about flattening too.
Here's where the trap opens. The founders “cargo-culting” the Block playbook into a $3M ARR company are about to make their bottleneck worse than it has ever been.
