Jack Dorsey says he wants all 6,000 Block employees reporting directly to him, betting that AI will make traditional management layers obsolete.
Jack Dorsey has a new organizational chart for Block, and it looks like a flat line. The Block CEO and cofounder told Sequoia Capital's "Long Strange Trip" podcast that his ideal structure would eliminate every management layer between him and the company's roughly 6,000 employees. That means no middle managers, no directors acting as intermediaries, just one executive and thousands of individual contributors connected through what he calls an "intelligence layer."
It sounds absurd, and Dorsey knows it. By his own admission, the idea is "ridiculous" under a traditional corporate hierarchy. But his argument hinges on a premise that is rapidly gaining traction across Silicon Valley: large language models can handle the coordination, oversight, and communication work that middle managers have historically owned. If AI becomes the connective tissue between leadership and staff, the reasoning goes, the old pyramid structure becomes unnecessary weight.
Block is not starting from scratch on this front. The company has already reduced its headcount by more than 4,000 employees, roughly 40 percent of its workforce, as Business Insider recently reported. The maximum distance between Dorsey and any remaining employee currently sits at five layers. His target is to compress that to two or three layers within a year.
Dorsey's vision rests on building what he described as a "mini-AGI," a company-specific artificial intelligence system capable of routing information, surfacing relevant data, and even making low-level operational decisions. In this model, AI does not just assist employees. It actively coordinates them, replacing the bureaucratic functions that middle managers typically perform, such as status updates, progress tracking, resource allocation, and escalation.
This is not purely theoretical. Companies like Shopify and Meta have already experimented with flattening their organizations while simultaneously investing in internal AI tools. Musk's own companies, including xAI and X, operate with notably flat structures and minimal middle management. The pattern is clear: tech leaders are looking at AI not just as a product to sell, but as an internal operating system that rewrites how companies function.
For Block specifically, the shift aligns with its broader pivot toward an "AI-first" identity. Dorsey has been publicly vocal about repositioning the payments company, formerly known as Square, as something closer to a technology platform. Eliminating management layers and replacing them with AI infrastructure is both a cost-cutting measure and a symbolic statement about where the company is heading.
What It Means for Workers and the Market
Here is the uncomfortable reality for middle managers everywhere: the role is under pressure from multiple directions. Layoffs across the technology sector have disproportionately affected management positions since late 2022. Companies discovered during the pandemic that smaller, flatter teams could maintain output. Now, AI tools are making those flatter structures more viable by automating the coordination work that justified manager headcount in the first place.
But the 6,000-person direct-report model raises serious questions about scalability and burnout. Even with AI handling routine coordination, Dorsey would need to exercise judgment on an enormous number of decisions daily. He acknowledged this on the podcast, describing his role as "the extra checkpoint" whose primary skill becomes judgment about what the company should build. Whether one person can effectively serve that function for thousands of employees without creating bottlenecks remains an open question.
There is also the cultural dimension. Middle managers often serve as translators between executive vision and frontline execution. They interpret strategy, mentor junior staff, and catch problems before they escalate. AI can surface data, but it cannot replace the human judgment that comes from understanding team dynamics, reading between the lines of a struggling employee's silence, or making a gut call on a risky project.
Still, Dorsey's bet is significant because it signals where the wind is blowing. If Block can demonstrate that a large company operates effectively with AI-managed coordination and minimal human management layers, expect other technology companies to follow. The pressure on middle management roles will intensify, and the skills companies value in leaders will shift toward strategic judgment, technical fluency, and the ability to work alongside AI systems rather than above them.
Watch what happens at Block over the next twelve months. If Dorsey gets anywhere close to his two-to-three-layer target, it will not just be a restructuring story. It will be proof that AI is reshaping corporate architecture from the inside out, and that the middle manager, as we have known it for decades, may be entering its final chapter.
