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More Reading from MarketBeat Can Upwork Maintain Its Comeback? Reasons to Be Bullish and BearishAuthor: 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 a more mixed legacy. Most — if not all — meme stocks never came close to their 2021 highs and today 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 appeared to be in danger of penny-stock status before COVID-19, when shares surged from $6 to $58 over 18 months. WARNING: Do Not Buy AI Stocks
While NVIDIA wobbles and the Magnificent 7 cool off, there's a backdoor AI play most investors are missing. It's not software. It's not chips. It's the physical infrastructure. The land, buildings, and power that make AI possible. Former Presidential Advisor Brad Thomas says Trump's Executive Orders are about to ignite a boom in this sector. And a small handful of companies are positioned to dominate. He names his top pick - completely free - in this time-sensitive video. Get the name and ticker of his #1 "Mandatory Payout" stock to buy now, FREE Of course, UPWK fell back under $10 a share shortly after the Federal Reserve began raising rates, and that run felt like a fever dream to many investors. But now Upwork is once again climbing, and this time the roughly 30% gain is driven by more than just cheap money. Can the stock sustain this momentum as we enter 2026? Here are 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 evolved into a more mature tech-sector business. Revenue has been growing, management has embraced AI, and the company is showing signs of long-term adaptability. Several fundamental and technical tailwinds underpin the recent surge, including these three factors. -
Revenue Growth Turning Profitable It's one thing to grow top-line sales; eventually those sales need to translate into profits, especially after seven years as a public company. Upwork has begun converting revenue into profitability and is showing progress across several key metrics. The company has beaten top- and bottom-line expectations, margins have reached record levels (29.6%), and the all-important Gross Services Volume (GSV) metric 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 brings us to the next factor. -
Successfully Mitigating AI Headwinds Many analysts feared generative AI would be a killshot for freelance marketplaces like Upwork, where many tasks are one-off gigs companies could theoretically replace with ChatGPT or Gemini. Instead of losing clients, Upwork embraced AI and adapted to hybrid human-plus-AI workflows. Companies can now combine human freelancers with specialized AI agents for more complex projects, and AI-driven GSV has grown more than 50% YOY. The company also launched UMA, its "work companion," to help freelancers and clients connect more efficiently. -
Technical Trends Point to More Upside Strong fundamentals can take time to show up in a stock price if technical tailwinds are absent. Upwork appears to have both: record sales, expanding margins, and improving technicals. 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 proved early rather than wrong. The 50-day SMA wobbled but held as support, and the stock moved back above its September 2025 high. The Relative Strength Index (RSI) is elevated but still below the overbought threshold of 70, suggesting there may be room for further gains. 2 Reasons to be Bearish on UPWK in 2026 Putting 2025 behind us, investors are rightly focused on 2026. For anyone considering a position in UPWK, keep these two risks in mind. -
Shrinking Gig Volume Is a Red Flag AI has helped overall revenue growth, but it has also exposed some vulnerabilities. GSV is growing overall, yet smaller jobs—those paying $300 or less—are disappearing as companies increasingly turn to generative AI to avoid onboarding one-off freelancers. If Upwork cedes those smaller gigs to AI tools or competitors like Fiverr International Ltd. (NYSE: FVRR), the marketplace could see GSV shrink again even if higher-value projects remain steady. -
Broader Labor Market Weakness Currently the macro backdrop looks stable: the Federal Reserve lowered rates again this month, and lower rates tend to 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. On top of that, the company's new Lifted platform for Enterprise clients is expected to require substantial integration costs, which management said could shave roughly 2% off margins in 2026. Margin stagnation combined with a slowing job market—or a recession—could reverse Upwork's profit progress and put significant pressure on the stock.
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