Jack Dorsey's fintech empire is quietly unraveling from within. Workers at Block, the company behind Square and Cash App, are describing a workplace transformed by continuous layoffs and mandatory AI tool adoption that's reshaping how one of Silicon Valley's most prominent fintech companies operates. The dual pressures of workforce reductions and forced automation are creating what insiders call a deteriorating culture at a company once known for its employee-friendly approach.
Block, Jack Dorsey's fintech conglomerate, is navigating a painful transformation that's exposing the human cost of Silicon Valley's AI-first future. Employees at the company are painting a picture of an organization caught between aggressive automation and persistent job cuts, a combination that's fundamentally altering the workplace culture at one of the payments industry's most recognizable names.
The complaints center on what workers describe as continuous, rolling layoffs that have created an atmosphere of uncertainty while the company simultaneously mandates daily use of AI tools across its operations. It's a stark shift for Block, which operates both the Square point-of-sale system used by millions of small businesses and Cash App, one of the most popular peer-to-peer payment platforms in the US.
According to employee accounts reported by Wired, the dual pressures have fundamentally changed how people work at Block. The mandatory AI adoption isn't just an optional efficiency tool - it's become a daily requirement, suggesting the company sees automation as central to its future operations even as it reduces its human workforce.
The timing is particularly revealing. Block isn't alone in pushing AI adoption, but the combination with ongoing layoffs suggests a deliberate strategy to transform operations with fewer people and more automation. It's a pattern playing out across tech, but Block's approach appears more aggressive than most, with the rolling nature of the cuts creating sustained anxiety rather than a single restructuring event.
