Jack Dorsey Pitches AI as Replacement for Middle Managers as Block Cuts Nearly Half Its Staff

Jack Dorsey is positioning artificial intelligence as a structural replacement for middle management at Block Inc., outlining a vision in which AI systems coordinate work across engineering teams without the need for human supervisory layers. The comments came weeks after Block announced it was cutting nearly half its workforce, one of the largest proportional layoffs at a major tech company in recent memory. Dorsey framed the reductions as part of a deliberate organizational redesign rather than a cost-cutting response to market pressure. In Dorsey's model, AI handles the coordination, prioritization, and communication functions traditionally performed by middle managers, allowing engineers and other individual contributors to work more directly with leadership and with each other. The argument tracks with a broader pattern at several technology companies, where founders and executives have used AI adoption as justification for flattening organizational hierarchies. Block, which operates the Square payments platform and the Cash App consumer finance product, employed roughly 8,000 people before the layoffs were announced. The cuts represent a significant contraction for a company that expanded aggressively during the pandemic era and has since faced slower growth and margin pressure. Dorsey has long been skeptical of managerial overhead. His public statements on company structure have historically emphasized small, autonomous teams over traditional corporate hierarchies. The framing of AI as an organizational tool, rather than purely a product feature, represents a notable extension of that philosophy. The announcement raises questions about how AI systems will handle performance management, conflict resolution, and career development functions that middle managers currently provide alongside coordination work.