The timing of it was almost too exact. On a Thursday in early May, Upwork—a company founded solely on the notion that work could be divided into more manageable chunks and transported across borders via Wi-Fi—announced it was laying off about 25% of its own employees. 145 or so individuals. Before the majority of East Coast residents had finished their dinner, the stock fell 19%.
The wording made it hit harder than the typical tech layoff news. The founder of Upwork since 2020, Hayden Brown, did not follow the conventional wisdom regarding “rightsizing” or “evolving priorities.” “The two-pizza team is dead,” she said. The idea that a team small enough to be fed by two pizzas was the ideal unit of human productivity was first put forth by Jeff Bezos sometime in the early years of Amazon, and it quickly became a kind of secular gospel in Silicon Valley. In essence, Brown argues that AI has reduced the number of pizzas to just one. Perhaps half.
| Company Profile | Details |
|---|---|
| Company Name | Upwork Inc. |
| Founded | 1999 (as Elance), merged 2013, rebranded 2015 |
| Headquarters | Palo Alto & San Francisco, California |
| CEO | Hayden Brown (since January 2020) |
| Chairman | Thomas Layton |
| Industry | Freelance marketplace |
| Stock Ticker | Nasdaq: UPWK |
| 2025 Revenue | US$788 million |
| 2025 Net Income | US$115 million |
| Workforce Reduction (May 2026) | Approximately 24% (~145 jobs) |
| Restructuring Charges | $16 million to $23 million |
| Key AI Product | Uma AI assistant (launched 2024) |
| Founders | Bernard Sheth, Srini Anumolu, Sanjay Noronha, Odysseas Tsatalos, Stratis Karamanlakis |
She might be correct. This could also be what executives say when they need to explain a difficult decision with a thesis that goes beyond the quarterly figures. Both can be true simultaneously. Upwork’s revenue increased slightly from $192.7 million to $195.5 million in the first quarter. In fact, adjusted earnings exceeded analyst expectations. Thus, the business is not losing money. It’s restructuring while the lights are still on, which is the kind of action that tends to frighten investors more than a genuine crisis because it implies that management recognizes something that the market hasn’t yet factored in.
Beneath all of this lies a deeper irony. Upwork has been telling corporate America for more than ten years that freelancers found via an app could take the place of full-time employees. Some of the people who created that platform are now being replaced by AI. This is also being watched by the site’s freelancers. The tone of r/Upwork Reddit threads varies from pessimistic to fatalistic. In 2023, AI job postings on Upwork became the fastest-growing category, according to some posters, and the platform was feeding the thing that would eventually trim it.
Cloudflare, Coinbase, PayPal, and Freshworks all laid off employees this same week, according to the wider tech news. The pattern is beginning to resemble a coordinated reset of what white-collar work is expected to look like in 2026 rather than a collection of individual choices. With the possible exception of Brown, who at least had the guts to identify what she believes is occurring, nobody is speaking it aloud in those precise terms.
It remains to be seen if the two-pizza team is truly dead or only momentarily sidelined. Skeptics will point out that every automation wave over the past 50 years has predicted something’s demise, but the majority of those things are still alive, albeit in different ways. This time is different, according to optimists, because technology can now write code, draft proposals, summarize meetings, and create graphics—all tasks that previously required, well, a small team. Observing this from the outside gives the impression that we are in the midst of a transition that no one is quite sure how to quantify just yet. One early data point is this week’s stock chart for Upwork. There will be more.
