Is it finally happening? Is AI about to integrate itself into workforces as we have never seen before? You can say yes, you can say no, but after what Jack Dorsey did, you have to start paying attention a lot more closely. But before we discuss what we did, let’s discuss who he is.
Who is Jack Dorsey?
Dorsey is best known as the co-founder of two major tech companies: Twitter (now called X Corp.) and the financial-technology company Block, Inc. (formerly Square). By co-founding Twitter, he has shaped social media. In 2006, Dorsey helped launch Twitter alongside Biz Stone, Evan Williams, and Noah Glass.
Together, this team introduced: The idea of short public messages (“tweets”), a real-time information network, and key features like @mentions, hashtags (#) (popularized on the platform), and retweets. The impact that Twitter has had on society may be even greater. Twitter became one of the world’s most influential communication platforms. It is widely used by politicians, journalists, and celebrities.
Dorsey served as CEO at Twitter twice. From 2006–2008 (first CEO) and then as 2015–2021 (returned as CEO). One of his most controversial decisions occurred in 2021 when Twitter permanently banned Donald Trump after the January 6 United States Capitol attack. Dorsey later said he believed the ban was the right decision but a dangerous precedent for the internet.
Then, in 2009, Dorsey founded Square (now Block Inc.). This transformed how credit card payments would be made forever. The idea was for small businesses to accept credit card payments on a smartphone using a tiny card reader. However, this evolved into a much bigger ecosystem. This included: Cash App, which allows peer-to-peer payments. Square POS systems for businesses. Small-business lending. And cryptocurrency investing and purchasing services. In 2021, Square was renamed Block to reflect a broader focus, including blockchain technology.
In 2021, Dorsey stepped down as Twitter CEO and was replaced by Parag Agrawal. In 2022, Twitter was purchased by Elon Musk and eventually rebranded as X. Dorsey later criticized parts of the company’s evolution but also said he felt responsible for how centralized Twitter became.
What Happened at Block?
Block had already been trimming staff for a couple of years. Around 931 employees were laid off in March 2025 (about 8% of staff). Before that, 1,000 employees were laid off in January 2024. But what is making all the headlines now is that about 4,000 employees were laid off. That is roughly 40% of the company’s workforce.
Dorsey said the company could run with smaller teams because of AI tools, arguing that technology allows fewer workers to do the same work. Dorsey’s explanation in an internal message to staff said the company was making changes to improve organizational efficiency and performance. He cited three main reasons: Strategy changes, performance management, and flattening the organization.
Some projects and teams were no longer aligned with Block’s direction, and the company was removing employees it believed were not meeting expectations. Block wanted fewer management layers and a leaner structure. He emphasized the cuts were not about replacing workers with AI, though the company was investing in AI tools.
The Email Jack Sent to Employees
The email opened with….“today we’ll be making some org changes, including eliminating roles… i want to give you all the straight facts.”
He then explained the layoffs were happening for three reasons:
Strategy
“reducing from teams that are off strategy, and fixing our discipline ratios.”
Performance
“parting ways with people with a ‘below’ or trending towards ‘below.’”
Hierarchy
“driving to flattening our org to a max depth of innercore+4.”
He also gave specific numbers for that round:
391 employees cut for strategy reasons
460 employees cut for performance reasons
80 managers removed to flatten management layers
In a later message explaining the massive 4,000-person layoff, Dorsey wrote:
“we’re not making this decision because we’re in trouble… our business is strong.”
He said the change was happening because AI tools allow smaller teams to do more work:
“intelligence tools… paired with smaller and flatter teams, are enabling a new way of working.”
Dorsey also included an apology:
“to those of you leaving… i’m grateful for you, and i’m sorry to put you through this.”
He added that the layoffs weren’t meant as a reflection on their contributions.
So there you have it, folks. Is this the start of something bigger? Are other companies going to follow suit? Maybe, maybe not. Personally, I feel like they will be. The craziest part is that after this was announced, Block’s stock price went up!!! Can you believe that? Layoffs are usually a bad sign, and stocks fall from this kind of news. Not in this case. And I know why. That is a whole lot of salaries that will not have to be paid any longer. You are talking about a ton of money.
I’ll leave you with the numbers. On February 22nd, before the news, Block’s stock price was $50.75. Today after the news has settled in, the stock price is $66.33. You figure it all out!
