Jack Dorsey's Block is undergoing a controversial transformation that's rattling employees across its Square and Cash App divisions. Workers are describing a deteriorating culture where ongoing layoffs run parallel to mandatory daily AI tool usage, according to a new report from Wired. The dual strategy marks one of the most aggressive corporate AI adoption mandates in fintech, even as the company continues trimming its workforce through what insiders call 'rolling' cuts that create constant anxiety.
Block, Jack Dorsey's fintech empire behind Square and Cash App, is conducting a high-stakes experiment that's leaving employees anxious and industry watchers divided. The company is simultaneously cutting staff through what workers describe as 'rolling layoffs' while mandating that remaining employees use AI tools every single day.
According to employees who spoke with Wired, the culture at Block has deteriorated significantly as the dual pressures mount. Workers report constant uncertainty about job security even as they're being pushed to integrate artificial intelligence into their daily workflows. The message is clear but uncomfortable: embrace AI or risk becoming redundant.
The timing tells its own story. While Block hasn't disclosed specific headcount numbers for these latest cuts, the rolling nature means teams never quite know when the next round will hit. Unlike traditional layoff cycles that happen once and allow companies to stabilize, this approach keeps employees in perpetual evaluation mode. One worker described it as 'death by a thousand cuts' where you're simultaneously proving your worth while learning to use the tools that might eventually replace you.
Block's mandatory AI adoption policy stands out even in an industry racing to implement machine learning and automation. Employees aren't just encouraged to experiment with AI tools - they're required to use them daily. The company has reportedly built this expectation into performance evaluations, making AI fluency a core competency rather than a nice-to-have skill.
