​ Block Layoffs Continue as Jack Dorsey Cuts Jobs Again
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Twitter Co-Founder Jack Dorsey Said Repeat Layoffs Would Hurt Trust, Then Cut Jobs Again: What Went Wrong at His Fintech Empire

Months after warning that repeated layoffs would damage trust, Twitter co-founder Jack Dorsey's fintech empire is cutting jobs again, even as profits rise and questions mount about its AI strategy and growing financial challenges.

Lacy J by Lacy J
November 7, 2026
in Tech
Reading Time: 3 mins read
Twitter Co-Founder Jack Dorsey Said Repeat Layoffs Would Hurt Trust, Then Cut Jobs Again: What Went Wrong at His Fintech Empire

Twitter Co-Founder Jack Dorsey Said Repeat Layoffs Would Hurt Trust, Then Cut Jobs Again: What Went Wrong at His Fintech Empire

Block layoffs are continuing in November 2026, with Jack Dorsey’s company cutting positions across Cash App and Square despite rising profits. A message reviewed by Business Insider told employees on Wednesday, November 4, that their roles were being eliminated. The total affected remains undisclosed. Eight months earlier, Dorsey announced plans to eliminate more than 4,000 jobs, arguing that one decisive reduction was better than repeated rounds. Now the cuts have returned.

The story began in 2009, when Dorsey and Jim McKelvey founded Square to make card payments easier for small businesses. The company expanded into Cash App, lending, and bitcoin. Square became Block in December 2021, then acquired buy now, pay later provider Afterpay in 2022. Block also purchased a majority stake in Jay-Z’s music service Tidal in 2021. Its ambitions were growing quickly, and so was its workforce.

By late 2023, Block employed 13,000 people. Dorsey acknowledged that expansion had gotten ahead of the business. He wrote, “The growth of our company has far outpaced the growth of our business and revenue.” Block layoffs followed, including approximately 1,000 jobs in January 2024 and 931 more in March 2025. What began as a hiring correction had become a recurring feature of the company’s operations.

Then came February 26, 2026. Dorsey said Block would shrink from more than 10,000 employees to fewer than 6,000, cutting over 40% of its workforce. He wrote, “We’re not making this decision because we’re in trouble. Our business is strong.” He argued AI tools were changing how companies operated, allowing smaller teams to accomplish more. Block recorded $495 million in restructuring charges tied to that plan through September 2026.

Dorsey explained why he wanted the layoffs completed at once. “Repeated rounds of cuts are destructive to morale, to focus, and to the trust that customers and shareholders place in our ability to lead,” he wrote. The latest Block layoffs now challenge that approach. The company says its February restructuring ended in the second quarter, yet employees are once again being told their jobs are disappearing.

This week’s internal notice identified Customer Operations, Risk Operations, and Learning & Content Operations. It described “reducing the number of roles, changing some responsibilities, and shifting some reporting lines.” The message referred to “using better tools to handle routine tasks” and focusing employees on more complex work, but did not specifically mention AI. Some workers will leave with separation packages, while others face a consultation process. Block declined to comment on the latest cuts.

According to an internal FAQ reviewed by Business Insider, affected US employees are eligible for at least seven weeks of severance, plus another week for each year of service. Those signing and following a separation agreement can receive pay during a 90-day period without working, three months of health premium coverage and $5,000 in transition assistance. February’s package included six months of healthcare coverage. For workers facing Block layoffs, the financial details are hardly abstract.

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Block’s profits tell a different story. On November 3, the company reported third-quarter gross profit of $3.24 billion, up 22% from a year earlier. Cash App’s gross profit rose 27% to $2.07 billion, while Square’s increased 14% to $1.16 billion. Block raised its 2026 gross-profit forecast to $12.63 billion and projected annual savings of $800 million to $900 million from February’s restructuring. These job cuts are happening during growth, not a reported business collapse.

But growth has not erased mounting expenses and oversight problems. Block’s losses on transactions, loans and consumer receivables reached $601.7 million in the third quarter, up nearly 66% year over year. Its latest filing also disclosed an October agreement in principle with the Justice Department concerning alleged anti-money-laundering failures. The proposed arrangement carries a gross monetary component of approximately $964 million and an expected net payment of $764 million after credits for earlier resolutions.

That Justice Department deal is not final and requires court approval. Under a proposed three-year deferred prosecution agreement, prosecutors would defer a charge alleging Block failed to maintain an effective anti-money-laundering program. Block has set aside $764 million and warns the cost could be higher. The SEC separately ended its related investigation in March without recommending enforcement. These legal developments have not been shown to cause Block layoffs, but they illustrate the compliance costs of operating a large financial platform.

Cash App faced scrutiny. In January 2025, federal consumer regulators ordered Block to pay a $55 million penalty and provide up to $120 million in customer redress over fraud handling and customer support failures. New York regulators reached a $40 million settlement over compliance deficiencies in April. Block did not admit to the New York regulator’s findings. Meanwhile, employees told WIRED earlier this year about deteriorating morale and pressure to use AI tools.

Dorsey has maintained that February’s enormous reduction reflected technological change rather than leftover pandemic overhiring. The continuing Block layoffs leave a question unanswered: Can the company protect customers, manage financial risks and deliver better products with thousands fewer people? Its profits suggest the business still has momentum. Its employees are seeing how much that momentum now depends on doing more with less.

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Lacy J

Lacy J

I go by the name Lacy J. Opinion pieces are my thing. I speak on politics and entertainment with a real, unfiltered perspective, breaking down what’s happening in a way that’s clear, direct, and actually relevant to the culture.

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