At Block Inc., the financial technology company behind Square and Cash App, something unusual is happening. Employees are required to send weekly email updates to CEO Jack Dorsey, who uses artificial intelligence to summarize thousands of messages. Meanwhile, layoffs are unfolding not as a single announcement but as a slow, weeks-long process that has left staff in limbo.

The company, co-founded by Dorsey in 2009 after his departure from Twitter, has approximately 11,000 employees. Up to 10 percent may lose their jobs by the end of February 2026. Management says it’s about performance. Workers say something else is happening.

The Rolling Layoffs

Unlike traditional layoffs announced in a single day, Block has chosen to execute terminations over several weeks. Staff members don’t know week to week whether they’ll still be employed.

“We don’t yet know if our livelihoods will be affected, and this makes it incredibly hard to make major life choices without knowing if we still have a job next week,” read one employee complaint submitted during an all-hands meeting with Dorsey, according to a transcript seen by WIRED.

Arnaud Weber, Block’s engineering lead, sent an email after the first wave characterizing the departures as performance-related. “As part of our 2025 performance cycle, we have parted ways with teammates who weren’t meeting the expectations of their role,” Weber wrote. “These departures were based on clear performance gaps.”

Multiple employees who spoke with WIRED disagreed with this framing, suggesting the layoffs reflect broader cost-cutting disguised as merit-based decisions.

The AI Mandate

At the center of Block’s current culture is an unusual requirement: workers must send weekly email updates to Dorsey, who then uses generative AI to summarize the thousands of messages he receives.

During the same all-hands meeting, Dorsey said that frequent topics cited by workers in their latest messages included “widespread concerns about layoffs,” “performance anxiety,” and “the tension between accelerating delivery through AI adoption versus maintaining code quality and engineering rigor.”

He also stressed that remaining workers should be using generative AI tools to maximize productivity, warning that Block risked being outpaced by competitors if they didn’t embrace the technology.

“Top-down mandates to use large language models are crazy,” one current Block employee told WIRED. “If the tool were good, we’d all just use it.”

Two Perspectives on AI at Work

The Management Case

From leadership’s perspective, AI adoption isn’t optional—it’s survival. In a competitive fintech landscape, companies that fail to leverage every available efficiency risk falling behind.

Dorsey’s comment that “a sizable portion of our population have been phoning it in” reflects a frustration that some workers weren’t keeping pace with the company’s needs. From this view, the layoffs aren’t callous—they’re necessary pruning.

The Worker Reality

Employees paint a different picture. The combination of rolling layoffs, mandatory AI tools, and AI-monitored communications has created what one worker called a “crumbling” culture.

“Morale is probably the worst I’ve felt in four years,” read one complaint submitted to Dorsey.

The concerns break down into several themes:

Surveillance anxiety: When your CEO uses AI to summarize your weekly updates, every word feels weighted.

Tool fatigue: Mandatory adoption of any tool, no matter how useful, breeds resentment.

Job insecurity: The rolling nature of the layoffs means no one can plan.

Burnout: The pressure to “perform” while simultaneously learning new AI tools creates a perfect storm of stress.

The Bigger Picture

Block is not an isolated case. Across the technology sector, companies are navigating similar tensions. AI is no longer experimental—it’s expected.

The answers matter because Block is likely a preview of what’s coming to many workplaces.

What Comes Next

Block hasn’t commented publicly on the internal situation. The company continues to operate Square, Cash App, and its other financial services products while the layoffs unfold.

Companies can mandate tools. They can use algorithms to monitor communications. They can describe layoffs as performance-based. But they cannot force a culture of innovation through fear.

Sources: WIRED, Bloomberg, internal Block communications