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Eliza Lasky
Weiss Advocate
Can Upwork Maintain Its Comeback? Reasons to Be Bullish and Bearish
By Dan Schmidt. Article Published: 12/17/2025.
Key Takeaways
- Upwork was a popular meme stock in 2021, but the company hasn't come close to matching those highs in the 4 years since.
- Despite its negative reputation, Upwork has become a profitable enterprise that's embraced AI for more complex jobs.
- While fundamental and technical tailwinds are in place, a few factors are still weighing on the stock that investors should be aware of as they enter 2026.
Traders might fondly remember the meme-stock era of 2021, but the companies involved have had a mixed fate. Most (if not all) meme stocks never came close to their 2021 highs and now sit in the market's dustbin.
One of those former high-flyers is Upwork Inc. (NASDAQ: UPWK), the online gig marketplace that went public in 2018. Upwork looked headed for penny-stock status before COVID-19, then shares surged from about $6 to $58 over 18 months.
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[[Click here now to view.]]Of course, UPWK fell back under $10 a share shortly after the Fed began raising rates, and the whole run felt like a fever dream.
But now Upwork is once again rising — and this time the roughly 30% gain is backed by more than just easy money.
Can the stock sustain this momentum as we enter 2026? We've got three reasons to be bullish, and two reasons to remain cautious.
3 Reasons to be Bullish on UPWK in 2026
If Upwork continues to climb, 2025 may be remembered as the year the company matured within the tech sector. Revenue is rising, and the company has embraced AI — a sign of long-term adaptability. There are both fundamental and technical tailwinds behind this surge, including the following three factors.
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Revenue Growth Becoming Profitable
Growing top-line sales is one thing; turning those sales into sustainable profits is another, especially after seven years as a public company. Upwork has started to convert sales into profits and is showing growth across several key areas. The company has been beating top- and bottom-line expectations, margins reached a record 29.6%, and Gross Services Volume (GSV) returned to growth in Q3 2025, up 2% year-over-year (YOY). During the Q3 conference call, Upwork raised its full-year revenue and EBITDA guidance and highlighted its AI advances, which leads to the next point.
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Successfully Mitigating AI Headwinds
Many analysts expected generative AI to be a kill shot for freelance marketplaces like Upwork, where many tasks are one-off gigs companies might try to replace with ChatGPT or Gemini. Instead of losing clients, Upwork embraced AI for hybrid workflows. Companies can now combine human freelancers with specialized AI agents for complex projects, and AI-related GSV has grown more than 50% YOY. The company also introduced UMA, its "work companion," to help freelancers and clients find each other more efficiently.
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Technical Trends Point to More Upside
Fundamentals can take time to show up in a stock price if technical tailwinds are absent. This time, Upwork has both: record sales, expanding margins, and supportive technical indicators. The stock sent mixed signals when the price dipped despite a Golden Cross forming between the 50-day and 200-day simple moving averages (SMAs).
The Golden Cross wasn't wrong — it was early. The 50-day SMA wobbled but held as support, and the stock quickly climbed back above the 2025 high it notched in September. The Relative Strength Index (RSI) is elevated but still below the overbought threshold of 70, suggesting there could be more upside.
2 Reasons to be Bearish on UPWK in 2026
Setting 2025's performance aside, investors are focused on what will happen in 2026. For those considering a position in UPWK, watch these two risks.
-
Shrinking Gig Volume Is a Red Flag
AI has helped Upwork's revenue growth, but it has also exposed vulnerabilities. While GSV is growing overall, smaller jobs paying $300 or less are disappearing as companies turn to generative AI to avoid onboarding costs associated with one‑time freelancers.
If Upwork cedes these smaller gigs to AI or competitors like Fiverr International Ltd. (NYSE: FVRR), the marketplace could shrink in GSV terms — even if higher-level projects remain plentiful.
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Broader Labor Market Weakness
Currently, the macro picture for Upwork looks stable: the Federal Reserve recently lowered rates, and lower rates often help small-cap stocks with real cash flow and reasonable valuations. But the labor market is the canary in Upwork's coal mine, and the company's Enterprise segment (which serves large professional clients) has already shown signs of weakness this year.
Also, Upwork's new Lifted platform for Enterprise clients will likely require substantial integration costs, which management expects could shave roughly 2% off margins in 2026. Margin pressure combined with a slowing job market or a recession would likely reverse Upwork's profit trajectory and weigh on the stock.
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