• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
AIFinance

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
Down Arrow Button Icon
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

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.

Recommended Video

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.

In 2001, Fortune first convened “The Smartest People We Know,” bringing together CEOs and founders, builders and investors, thinkers and doers. Since then, Fortune Brainstorm Tech has been the place where bold ideas collide. From June 8–10, we will return to Aspen—where it all began—to mark 25 years of Brainstorm. Register now.
About the Author
Sheryl Estrada
By Sheryl EstradaSenior Writer and author of CFO Daily
LinkedIn iconTwitter icon

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.

See full bioRight Arrow Button Icon

Latest in AI

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Lists Calendar
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Lists Calendar
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in AI

James Uthmeier
LawOpenAI
Florida launches criminal probe into OpenAI to see if ChatGPT is responsible for fatal Florida State shooting
By Mike Schneider and The Associated PressApril 21, 2026
8 hours ago
Sequoia partner Julien Bek sitting on a stool and holding a microphone while speaking to an audience. Behind him is a stage that looks like a forest.
AIEye on AI
Are services the new software? This venture capitalist thinks the future is in selling AI-delivered outcomes, not AI-powered products
By Jeremy KahnApril 21, 2026
8 hours ago
Double exposure photograph of a portrait of Mark Zuckerberg and a telephone displaying the Meta group s artificial intelligence logo at Kerlouan in Brittany in France on April 11 2025. (Photo by Vincent Feuray / Hans Lucas / Hans Lucas via AFP) (Photo by VINCENT FEURAY/Hans Lucas/AFP via Getty Images)
AIMeta
Meta will start tracking employees’ screens and keystrokes to train AI tools
By Eva RoytburgApril 21, 2026
9 hours ago
Google Cloud’s next big moment—and what it needs to continue its ascent
AIGoogle
Google Cloud’s next big moment—and what it needs to continue its ascent
By Alex Kantrowitz, Marty Swant and Big TechnologyApril 21, 2026
10 hours ago
The inside of a data center in Ashburn, VA.
EnvironmentData centers
Data centers are dealing hidden damage to environmental and public health—costing the economy $25 billion every year
By Tristan BoveApril 21, 2026
10 hours ago
‘They’re sweating’: Why Japanese giants are pouring money into Silicon Valley startups
AsiaJapan
‘They’re sweating’: Why Japanese giants are pouring money into Silicon Valley startups
By Nicholas GordonApril 21, 2026
14 hours ago

Most Popular

$166 billion in tariff refunds just became available, but small businesses may already be at a disadvantage
Law
$166 billion in tariff refunds just became available, but small businesses may already be at a disadvantage
By Sasha RogelbergApril 20, 2026
1 day ago
Jeff Bezos once gave Eva Longoria and the admiral behind Osama bin Laden's capture $100 million—but she says you don't need wealth to give back
Success
Jeff Bezos once gave Eva Longoria and the admiral behind Osama bin Laden's capture $100 million—but she says you don't need wealth to give back
By Orianna Rosa RoyleApril 21, 2026
21 hours ago
The tables have turned: Florida and Texas are the biggest losers in the housing market as Ohio emerges a surprise winner
Real Estate
The tables have turned: Florida and Texas are the biggest losers in the housing market as Ohio emerges a surprise winner
By Sydney LakeApril 21, 2026
10 hours ago
'Something sinister could be happening': FBI looks into dead or missing nuclear and space defense scientists tied to NASA, Blue Origin, and SpaceX
Politics
'Something sinister could be happening': FBI looks into dead or missing nuclear and space defense scientists tied to NASA, Blue Origin, and SpaceX
By Catherina GioinoApril 21, 2026
9 hours ago
This talent CEO says laid-off tech workers are ignoring a $300K ‘white-collar trade job’ with 81K openings a year
Economy
This talent CEO says laid-off tech workers are ignoring a $300K ‘white-collar trade job’ with 81K openings a year
By Jake AngeloApril 20, 2026
1 day ago
Meet John Ternus, the 51-year-old former swimming champ who will succeed Tim Cook as Apple CEO
Big Tech
Meet John Ternus, the 51-year-old former swimming champ who will succeed Tim Cook as Apple CEO
By Dave Smith and Fortune EditorsApril 20, 2026
1 day ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.