Tech layoffs are coming in thick and fast in the age of AI.
Upwork CEO Hayden Brown announced on May 7, 2026, that the company would be cutting approximately a quarter of its workforce. The message, shared with employees and later published on Upwork’s website, frames the decision as both a response to near-term economic headwinds and a deliberate structural bet on AI-powered, leaner teams.
“Two pizza teams are dead,” Brown wrote bluntly in the memo. “AI means smaller, differently resourced teams in product and engineering can make a bigger impact than ever.” The statement is striking coming from the CEO of a platform that exists to connect businesses with freelance talent — a business model whose very premise is that human work is abundant and in demand.
What Brown Said
Brown cited two reasons for the cuts: speed and profitability. He argued that smaller teams move faster, pointing to Upwork’s 2024 layoff followed by strong 2025 execution as evidence. He also acknowledged that Q1 2026 data signals slower near-term growth, and that the company needs to hit profitability targets in a tighter environment.
The restructuring was not incremental. Brown said the company rethought every function from scratch — scrutinising what it takes to run each part of the business using both people and technology — consolidating redundant work and collapsing workflows to reduce handoffs.
“Fewer layers means faster decisions,” he wrote. “Flatter is better.”
Notifications will go out the week after the announcement, with an All Hands scheduled for May 8 and a broader company meeting planned for the week of May 18.
A Pattern Playing Out Across Tech
Upwork is not alone. The past several months have seen a drumbeat of similar announcements across the technology industry, with AI cited — explicitly or implicitly — as both the enabler and the justification.
Coinbase cut 14% of its workforce just days before Upwork’s announcement, with CEO Brian Armstrong describing a vision of AI agents doing the heavy lifting while humans operate at the edges. Block laid off 40% of its staff in February 2026, with Jack Dorsey explicitly naming AI as the cause — one of the most direct such statements from a major tech CEO. S&P 500 headcount fell in 2025 for the first time since 2016, with the combined workforce dropping by roughly 400,000 — ending eight consecutive years of growth. Upwork competitor Fiverr too had laid off 30% of its workforce late last year.
The org-design logic Brown articulates — flatter hierarchies, smaller teams, AI handling coordination — also echoes what Jack Dorsey told Block employees after his own restructuring: that AI now does the information-routing work that layers of management once existed to perform.
The Irony Is Hard To Miss
Upwork is, at its core, a marketplace for human work. It built its business on the proposition that companies need flexible access to skilled freelancers. Now its own CEO is declaring that AI renders large internal teams obsolete — a message that carries uncomfortable implications for the freelancers and independent professionals the platform serves.
To be fair, Brown’s memo does not claim AI has replaced Upwork’s workers. The rationale is operational: consolidating workflows, eliminating redundant roles, and building a leaner structure for a more competitive environment. But the language — “rethink the company from the bottom up,” “AI means smaller teams” — is precisely the framing that has accompanied workforce reductions across the industry, from McKinsey to Amazon to Salesforce.
Whether AI is the genuine driver or a convenient narrative remains contested. But the practical outcome is the same: thousands of workers losing their jobs at companies that describe themselves as leaning into an AI-first future.
What Comes Next
Brown expressed confidence in Upwork’s trajectory, noting that its 2025 “refounding” — a rebuild of product, customer focus, and operations — has positioned the company well for growth. The implication is that this round of cuts is not a sign of distress but of ambition: moving faster with a smaller, more capable team.
For the roughly 25% losing their jobs, Brown offered gratitude and a promise of support. For those staying, he promised more detail on future plans after May 18.
The broader workforce will be watching. Upwork is a bellwether — a company that sits at the intersection of AI, work, and the freelance economy. How it navigates the tension between advocating for human work and restructuring around AI may say more about where this is all heading than any think-piece or analyst report.