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Chronicles

The story behind the story

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Workers describe a deteriorating culture at Jack Dorsey's Block as morale plunges amid rolling layoffs and a push to use AI tools to improve productivity

Workers describe a deteriorating culture at Block, the company behind Square and Cash App, where layoffs continue and employees are expected to use AI tools daily.

Wired Reece Rogers

Context & Ripple Effects

Block's workforce pressure was already visible in reports that jobs could be eliminated during annual performance reviews, putting up to 10% of the workforce at risk. This account adds the employee-level consequence: the cuts and daily AI-use mandate are being experienced together rather than as separate initiatives.

The story also sits in a longer arc of deeper Dorsey involvement at Square during an earlier period of strain, followed by reporting on a 40% reduction in Block's workforce and Dorsey's “mini AGI” ambition. That sequence makes workplace adoption of AI central to Block's operating model, not simply an optional software rollout.

First-order effects

  • Block employees face a more uncertain working environment as rolling job cuts coincide with an expectation to use AI tools daily; morale and trust are the immediate operational costs.
  • Management gains a clearer mechanism to standardize productivity expectations around AI across the company, while Square and Cash App teams must absorb the disruption of fewer or changing colleagues.

Second-order effects

  • Teams may prioritize work that can be demonstrated, measured, or accelerated through AI tools, shifting managers' evaluation criteria and reducing time for work whose output is less easily captured.
  • The combination of layoffs and AI mandates raises retention risk for experienced staff, which can make preserving product and operational knowledge harder even as Block seeks efficiency gains.

Third-order effects

  • If this approach persists, Block becomes a test case for whether AI-led workforce compression can sustain product execution without eroding the organizational trust needed to retain talent.
  • The broader pressure is toward treating AI adoption as a management and labor-model decision—not merely a tooling choice—making culture, measurement, and accountability increasingly intertwined.

The trend: This is part of the shift from voluntary workplace AI experimentation to AI use being embedded in productivity targets and workforce restructuring.

Discussion

  • @prietschka Paul Rietschka on bluesky
    This is certainly a product of Dorsey mismanaging the company for years.  —  Many missed opportunities.  —  But this is going to be the route of so many companies in tech as the “real” AI revolution rolls out, i.e., mandated use, layoffs, failed projects, more layoffs, rinse and …
  • @rtehrani Rich Tehrani on x
    After hundreds of workers were laid off in early February from Jack Dorsey's Block, some of the people remaining at the company say the internal culture has devolved to a point where performance anxiety is running rampant, using generative AI is required, and overall morale is
  • @thiccreese Reece on bluesky
    NEW: “Top-down mandates to use large language models are crazy,” says one current Block employee.  “If the tool were good, we'd all just use it.”  —  My latest for @wired.com  —  www.wired.com/story/inside...
  • r/technews r on reddit
    Inside the Rolling Layoffs at Jack Dorsey's Block