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Jack Dorsey calls for elimination of middle managers at Block Inc, replacing them with AI

Block Inc. CEO Jack Dorsey co-authored an essay arguing that AI makes middle management obsolete, as the company cuts 40% of its workforce. The new model replaces managers with individual contributors, DRIs, and player-coaches, using AI systems to route information. This signals a permanent shift that could influence other tech companies.

read3 min views1 publishedJun 20, 2026
Jack Dorsey calls for elimination of middle managers at Block Inc, replacing them with AI
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Block's CEO co-authored an essay arguing that artificial intelligence makes traditional management layers obsolete, as the company slashes 40% of its workforce

Jack Dorsey wants to fire your boss. And your boss’s boss. And probably the person who manages the conference room calendar, too.

The Block Inc. CEO co-authored an essay titled “From Hierarchy to Intelligence” with Sequoia Capital’s Roelof Botha, laying out a vision where AI replaces the traditional middle-management layer that has defined corporate America for decades. Block has already cut approximately 4,000 jobs, reducing its workforce by about 40%, from over 10,000 employees to roughly 6,000.

The manifesto and the math #

The essay, published on March 31/April 1, 2026, traces the origins of corporate hierarchy back to Roman military structures, through 1840s US railroad management frameworks, past post-WWII American corporate pyramids, and into today’s matrix organizations. Their conclusion: all of it is outdated infrastructure built for a world that no longer exists.

The new organizational model at Block replaces traditional managers with three types of roles: individual contributors, Directly Responsible Individuals (DRIs), and player-coaches. DRIs own outcomes on specific projects. Player-coaches are senior people who still do hands-on work while mentoring others. Neither role involves the classic middle-manager function of aggregating information from below and translating it for people above.

Block is building what the essay calls “world models,” AI systems designed to maintain real-time context about the company’s operations and customer insights derived from transaction data. Instead of a regional manager synthesizing weekly reports into a deck for a VP, these systems will route information dynamically and surface decisions to the people best positioned to make them.

Dorsey has been explicit that this isn’t a temporary belt-tightening exercise. The restructuring is framed as a permanent shift empowered by AI tools, a philosophical reorientation of how Block operates rather than a reaction to a bad quarter.

Why this matters beyond Block #

The essay’s co-authorship with Roelof Botha adds another dimension. Sequoia Capital is arguably the most influential venture firm in Silicon Valley, with a portfolio spanning the biggest names in tech. When a Sequoia managing partner puts his name on a document arguing that middle management is obsolete, it sends a signal to every founder and CEO in their network.

Dorsey’s advocacy for flatter organizations isn’t new. His tenure at Twitter was marked by periodic attempts to reduce bureaucratic layers. The difference now is that large language models and AI coordination tools have matured enough to make the theoretical arguments practically executable.

What this means for investors #

The financial logic is straightforward. Fewer employees means lower operating costs. If Block can maintain or grow its output with 6,000 people instead of 10,000, the margin expansion would be significant.

Block processes enormous volumes of transaction data through Square, Cash App, and its other products. That data becomes exponentially more valuable in a world model architecture, where AI systems can derive real-time customer insights and operational intelligence without human intermediaries.

Investors watching Block over the next several quarters should focus on two metrics: whether revenue per employee improves meaningfully, and whether product velocity — the pace at which Block ships new features and services — holds steady or accelerates.

Disclosure: This article was edited by Editorial Team. For more information on how we create and review content, see our

Editorial Policy.

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