Corporate structures built for the Roman legion are breaking under AI’s weight. Jack Dorsey told Brian Halligan that the traditional org chart, a 2,000-year-old relic for managing human-scale communication, is obsolete. At Block, he’s replacing it with what he calls a “mini-AGI” - an AI that ingests every Slack message, email, and code commit to become the company’s central nervous system.
The proof is in the cuts. Block executive Owen Jennings said on The a16z Show that the decades-long correlation between employee count and output “basically broke” in December 2025. The company responded by eliminating 40% of its development teams, shrinking 14-person feature groups down to squads of one to six. AI handles the rest through internal tools like Builder Bot, which autonomously writes, tests, and merges code.
This shift creates a new class of exhausted engineer. Simon Willison explained on Lenny’s Podcast that senior developers now orchestrate four or more AI agents in parallel, making high-level architectural decisions all morning. “By 11:00 a.m., I am wiped out,” he said. The work isn’t disappearing; it’s transforming from typing code to managing cognitive load across a fleet of simulated workers.
Simon Willison, Lenny's Podcast:
- AI is supposed to make us more productive.
- It feels like the people that are most AI are working harder than they've ever worked.
- >> Using coding agents well is taking every inch of my 25 years of experience as a software engineer.
The endpoint is the “dark factory.” Willison described companies spending $10,000 daily on tokens to run simulated employees that stress-test software 24/7. In this model, no human reads or writes code; safety depends on massive AI swarms. The risk, he warned, mirrors the Challenger disaster - confidence grows with each uneventful launch until a systemic, unverified flaw causes collapse.
For Dorsey, the goal is total fluidity. Block is deploying generative UI bots that create unique app interfaces for each user, moving from static code to on-the-fly assembly. The internal structure has been flattened to three roles: Individual Contributor, Directly Responsible Individual, and Player-Coach. Middle management is gone.
The transformation is early and messy. As noted on Presidio Bitcoin Jam, Block’s own rollout of new features like Bitcoin payments faces real-world friction from legacy hardware and fragmented software updates. But the direction is set. The company betting its future on intelligence networks, not org charts.
