The Roman legion was the most sophisticated management system of its time. It was designed to project power from Rome to the edge of the empire, across two continents, thousands of miles, with no electricity, no phone, no internet. The solution was hierarchy: named individuals with consistent spans of control, passing orders down and sending information back up the chain. It worked for two thousand years.
Jack Dorsey said something similar recently that stuck with Tom Blomfield, YC General Partner. Most companies today are organised like Roman legions. Human beings are the conduit for information flowing up and down. That is not a metaphor. It is a structural fact. The meeting exists to move information between people. The manager exists to translate between layers. The report exists to carry signal upward. The briefing exists to carry decisions downward.
AI breaks the assumption underneath all of it. If information no longer needs a human to move it, the structure built to move information becomes optional. Not all of it. But more than you think.
Why We Have Hierarchies
The org chart was not inevitable. It was invented. The Steam, Steel and Infinite Minds piece traces it specifically: the modern org chart was created by the New York and Erie Railroad in 1855, one of the first organisations that needed to coordinate thousands of people across vast distances. Hierarchy was the best available technology for that coordination problem. It worked. The railroad built it. Every company since copied it.
Most companies today have a structure designed for a coordination problem that predates the telephone. The org chart is not a description of how things should work. It is a solution to a specific technical problem: how do you move information reliably across distance and time without modern communication technology? The answer was: appoint a human at every node of the network.
For most of human history, that was the only available answer.
The Middle Does One Thing
When Cloudflare's Matthew Prince restructured 20% of his workforce, the company was not struggling. It was growing at 30%. His explanation was precise. The vast majority of those affected were measurers. Middle managers across the organisation, operations functions, finance teams: people whose primary work was measuring, relaying, translating, and moving information between layers that could not communicate directly.
"They were translators, people who existed to relay context between layers that could not talk directly. Agents do not just measure faster, they eliminate the need for human middleware entirely."
Human middleware. The phrase clarifies what hierarchy is and why it degrades. Every time you add a layer between a decision and the information that informs it, you introduce delay, distortion, and cost. Companies try to solve this with flatter structures, better tools, more meetings. The problem is the architecture. You are still running information through human nodes.
What AI Actually Changes
Tom Blomfield put it plainly: "If you think about most companies today, they are organised like a Roman legion where human beings are the conduit for information flowing up and down. AI basically breaks that. If you can imagine companies operating where AI is the conduit for information flowing, you move from a hierarchically organised company to a sort of intelligent AI-powered organisation."
Here is what that looks like in practice.
Information flows through humans.
Information flows through shared systems.
This Does Not Mean Fewer People
This is the part most CEOs misread.
The Roman legion did not become obsolete because humans became less capable. It became obsolete because better coordination technology existed. The people who built railroads, ran them, and managed them were not replaced by the org chart. The org chart replaced a different, slower coordination mechanism. The people stayed. The structure changed.
The same will happen with AI. Builders and sellers, people creating things and people connecting with customers, are not being replaced. What is being replaced is the work that exists only because humans had to carry information between other humans. That work is now being done by agents.
"I think that is actually a broken way of thinking about AI, taking the old way of working and adding a more powerful engine onto it. You can actually reimagine what a company is." — Tom Blomfield, YC General Partner
What Most Companies Are Not Doing
Most companies have added AI tools to the existing Roman legion. The ChatGPT subscription sits next to the email client. The Copilot sits inside the IDE. The org chart is unchanged. The information still flows through the same human nodes.
That is AI adoption. It is not AI transformation. The productivity gains are real and worth capturing. But the structural assumption underneath the org chart, that information requires a human to carry it, has not been touched.
Redesigning the company around intelligence requires answering a different question: which of your current human nodes exist primarily to move information, and what happens if agents take that role?
That is a management question, not a technology question. The technology is ready. The question is whether the company is willing to ask it.
The Roman legion served its era well. Two thousand years. So did the railroad's org chart. A hundred and seventy years. The question is not whether hierarchy is bad. The question is whether it is still the best available solution to the coordination problem you are trying to solve.
The Diagnostic is where this question gets practical.
Bring it to a free Diagnostic. 30–45 minutes, one conversation. It maps which functions in your company are running human middleware that agents can replace, and what the first rebuild looks like.
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