Jack Dorsey Wants AI to Do the Middle Manager's Job at Block

Your daily brief on leadership and business

Most companies give employees an AI assistant and keep the org chart as it is. Block's co-founder Jack Dorsey wants to replace a piece of the org chart itself. In a blog post written with Block's lead independent director Roelof Botha, he argued that AI can track projects, spot issues, assign work and share critical information faster than human managers can.

The post came weeks after Block cut about 4,000 employees, roughly 40% of its staff, in a restructuring Dorsey linked to the rapid acceleration of AI. Some of those who lost their jobs were later quietly brought back. According to the authors, Block is in the "early stages" of moving toward a model in which AI performs much of the coordination work that middle management does today.

Questioning the hierarchy

The core argument is that hierarchy itself is the bottleneck. "Hierarchy and middle management impede information flow," the authors wrote. They said the real question was never whether companies needed those layers, but whether humans were the only option for what the layers do. Their answer: not anymore. The ambition is a company built as "an intelligence, or mini-AGI."

In practice, Block's employees would fall into three roles:

• individual contributors, who build and maintain the operating systems;
• directly responsible individuals, who solve specific problems and can draw on whatever resources they need;
• player-coaches, who mentor and support others while still writing code and building.

Why remote work matters here

The authors tie the idea to remote-first working. In a company where work is already machine-readable, they argue, AI can continuously maintain a real-time picture of what is being built, what is blocked, where resources go and what is working, instead of waiting for managers to compile reports. People would still make the key business and ethical decisions.

The proposal is ambitious and, for now, unproven. But it frames a question every manager may soon face: which parts of the job are judgment and which are just moving information around? The second part, it seems, is officially up for grabs.