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She joined Block to build AI. Weeks later, AI cost her job.

Sheryl Estrada
By
Sheryl Estrada
Sheryl Estrada
Senior Writer and author of CFO Daily
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Sheryl Estrada
By
Sheryl Estrada
Sheryl Estrada
Senior Writer and author of CFO Daily
Down Arrow Button Icon
February 28, 2026, 5:00 AM ET
Block cut more than 4,000 jobs, citing efficiency gains from AI, underscoring how even AI-focused roles are vulnerable in today’s tech restructuring.
Block cut more than 4,000 jobs, citing efficiency gains from AI, underscoring how even AI-focused roles are vulnerable in today’s tech restructuring.GETTY IMAGES
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Block’s AI-fueled layoffs are a stark reminder of how little protection even the most future-facing roles have in today’s tech economy—and how quickly the ground can shift beneath the people building that future.

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On Thursday, Jack Dorsey, CEO and founder of Block—parent company of Square and Cash App—announced plans to cut more than 4,000 jobs, roughly 40% of the workforce, reducing headcount from over 10,000 to just under 6,000 as part of a sweeping restructuring. Dorsey tied the cuts directly to efficiency gains from the company’s AI rollout, Fortune reported.

“We’re already seeing that the intelligence tools we’re creating and using, paired with smaller and flatter teams, are enabling a new way of working which fundamentally changes what it means to build and run a company,” he wrote in a post on X.

The announcement, delivered just ahead of Block’s earnings report, sent shares up more than 20% in after-hours trading. In a Thursday note, Morningstar Senior Equity Analyst Brett Horn wrote that Block’s fourth-quarter growth accelerated meaningfully and that management’s 2026 guidance calls for material margin improvement as the company dramatically lowers its headcount. He maintained an $83 fair value estimate.

Still, Horn cautioned: “The long-term impact of dramatically reducing staff and betting on AI productivity gains is uncertain, in our view.”

Among those affected is Debbie O’Brien, a senior staff developer relations engineer in Applied AI at Block based in Mallorca, Spain. She had joined only weeks earlier to help developers adopt AI workflows using agents and the Model Context Protocol. According to her website, she has more than 15 years of experience in frontend development, over 20,000 LinkedIn followers, and 10,000 YouTube subscribers. Fortune reached out to O’Brien, but didn’t receive a response as of press time.

In a candid YouTube video posted Friday, O’Brien described learning—indirectly at first—that she might be among those laid off. She was in a training session when a manager abruptly ended the call and instructed everyone to check their email. Colleagues began posting in Slack that they had been “cut,” but O’Brien saw only Dorsey’s broad memo, not an individual notice.

Hours passed without clarity. “I don’t know. Do I have a job? Do I not have a job?” she recalls. Near 12:30 a.m., she said, “I opened the computer, and I just looked, and there I saw the DocuSign, basically the official termination process, and that I read through and had to sign, and then I have a meeting today to basically tell me how to return the computer and things like that. So at least that meant I could sleep, because then I knew, actually, I don’t have a job anymore.”

O’Brien had been working on Goose, Block’s open-source AI agent framework built around the Model Context Protocol. She says the team was “on the bleeding edge,” rapidly shipping automations—from tools that generate release notes and videos in minutes to agentic flows that let users order food through ChatGPT, powered by Block’s payments rails.

She is careful not to single out Dorsey, her managers, or Block’s leadership, describing the move instead as a binary “light switch” decision about risk and survival—one that other companies may soon confront.

But she is blunt about the broader lesson: “Our future is unstable in the tech industry.” After back-to-back layoffs—first from Microsoft and now Block—she says she no longer sees tech roles as inherently secure, even in high-demand fields like AI. Her advice is pragmatic: get personal finances in order, reduce fixed costs like housing, and plan for the possibility of repeated disruption.

If you have worked for Block or were recently laid off and want to share your experience, contact me at sheryl.estrada@fortune.com.

Subscribe to Fortune Gulf Brief. Every Tuesday, this new newsletter delivers clear-eyed, authoritative intelligence on the deals, decisions, policies, and power shifts shaping one of the world’s most consequential regions, written for the people who need to act on it. Sign up here.
About the Author
Sheryl Estrada
By Sheryl EstradaSenior Writer and author of CFO Daily
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Sheryl Estrada is a senior writer at Fortune, where she covers the corporate finance industry, Wall Street, and corporate leadership. She also authors CFO Daily.

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