Jack Dorsey and Roelof Botha think AI can make middle management obsolete 

For years, companies have been flattening their organizations and cutting down middle management. Weeks after slashing his staff by 40%, Jack Dorsey, CEO of payments company Block, foresees middle management’s complete extinction. 

In an essay published Tuesday, coauthored with Sequoia advisor Roelof Botha and titled “From Hierarchy to Intelligence,” Dorsey questioned the conventional wisdom of widely used organizational structures. 

“At Sequoia, we see that speed is the best predictor of startup success. Most companies are focused on AI as a productivity enhancer. Few are focused on the potential of AI to change how we work together,” they wrote. 

In February, Block laid off 4,000 employees, or about 40% of its workforce. Dorsey made his reasoning clear: “We’re already seeing that the intelligence tools we’re creating and using, paired with smaller and flatter teams, are enabling a new way of working which fundamentally changes what it means to build and run a company,” he wrote in a Feb. 26 X post.

Dorsey and Botha are rejecting what they see as 2,000 years of hierarchical organizational structures, starting with the Roman army, that relied...