Billionaire Block founder Jack Dorsey suggests radically reshaping manager roles in the age of AI

May 20, 2026

In February, billionaire Block (XYZ) founder and CEO Jack Dorsey laid off 40% of his workforce as part of an AI-driven efficiency push.

A string of job cuts followed. Tech execs fine-tuned their slide decks in subsequent management meetings, then uncorked headline-making mass layoff announcements of their own, blaming AI for reducing headcount.

The former Twitter founder is back with more news as tech firms eye further AI-driven efficiency gains.

The news: Dorsey says he isn’t done removing management layers at Block and changing the job requirements of a modern-day manager.

“So like right now … we’re about five layers deep. I would love to get that down to two to three by the end of the year,” Dorsey said at a JPMorgan conference on Tuesday. He was referencing the number of organizational layers beneath him.

Jack Dorsey, CEO of Twitter and co-founder & CEO of Square, attends the crypto-currency conference Bitcoin 2021 Convention at the Mana Convention Center in Miami, Florida, on June 4, 2021. (Photo by Marco BELLO / AFP) (Photo by MARCO BELLO/AFP via Getty Images)
Jack Dorsey, CEO of Twitter and co-founder & CEO of Square, attends the crypto-currency conference Bitcoin 2021 Convention at the Mana Convention Center in Miami, Florida, on June 4, 2021. (MARCO BELLO/AFP via Getty Images) · MARCO BELLO via Getty Images

Dorsey said that in the future, managers should be assigned to groups of potentially hundreds of people rather than to a single team. “You’re focused on helping [workers] get to mastery of their discipline and helping them think through their career and like how to think about problems and see around corners … but you don’t have to like tell them what to do. You can show them how to do it.”

As a start, “in engineering last year, we moved from a world of having pure managers to the requirement that every manager must be technical and they must contribute code. And that was just one step, and we need to do that throughout the organization for all of our other disciplines as well.”

What Dorsey is suggesting is a radically lean operating structure for a public company to speed up idea creation and execution. Plus, a completely reinvented role for managers.

Read more: Worried about job security? Take these 5 steps now to protect your finances.

2026, the year of the mass tech company layoff: The growing impact of AI is not just seen at Block this year, but also at Amazon (AMZN), Oracle (ORCL), Coinbase (COIN), Cloudflare (NET), and Meta (META).

With billionaire founder Larry Ellison still pulling the strings, Oracle reportedly laid off up to 30,000 workers across the US, Mexico, and other countries on April 1. Amazon has reportedly slashed 16,000 workers this year as part of its AI efficiency push.

Coinbase is fresh off announcing a 14% reduction in force this month. Cloudflare just cut bait with 20% of its workforce. And Meta is in the process of cutting 10% of its employee count.

Circle (CRCL) co-founder and CEO Jeremy Allaire recently doubled down on his call that we are just at the start of AI agents reshaping the US workforce.

“I think we’re very early in the impact of AI agents on the conduct of work and how that plays out through labor,” Allaire told me on Yahoo Finance’s Opening Bid (see video above).

Allaire issued an early warning about two months ago at the Economic Club of New York. He said AI-related job losses would soon pick up the pace and perhaps continue into 2027.

Allaire said Circle is aggressively leaning into AI, and it’s yielding results.

“Eight-five percent of our workforce is active on a weekly basis with AI coding tools and AI automation tools … our employees have built and deployed over 600 AI apps so far this year, and over 54% of those employees are nontechnical,” he said. “And so we’re making it central to what we do. The message that we have is this is one of the greatest opportunities ever for people in their careers to really get new superpowers.”

Bottom line: These headline-grabbing Big Tech layoff announcements are not a one-time blip. AI is moving fast, putting management teams at tech companies in constant workforce evaluation mode.

Investors are betting these evaluations will drive more efficiencies, more profits…and a higher stock price.

Brian Sozzi is Yahoo Finance’s Executive Editor and a member of Yahoo Finance’s editorial leadership team. Follow Sozzi on X @BrianSozzi, Instagram, and LinkedIn. Tips on stories? Email brian.sozzi@yahoofinance.com.

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