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Just For You Can Upwork Maintain Its Comeback? Reasons to Be Bullish and BearishWritten by Dan Schmidt. Published 12/17/2025. 
Key Points - 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 fared unevenly. Most (if not all) meme stocks never came close to their 2021 highs and currently 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 in danger of penny-stock status before COVID-19, then shares surged from about $6 to $58 over 18 months. These 'stock bets' hit different
In the last hour of every trading day, over $55 BILLION floods the market…And in the final 9 or 10 minutes, fortunes can be made. Most traders miss it completely. But my new system spots exactly where all that money is flowing, just before the biggest moves happen. The results have been crazy.I know a guy (Kenny) who averages $500 to $1,000 profit per trade every single day…With only two losing trades in 8 months. Want to see how it works? Check it out here. Of course, UPWK slipped 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 driven 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 skeptical. 3 Reasons to Be Bullish on UPWK in 2026 If Upwork continues to climb, 2025 may be remembered as the year the company matured into a tech-sector enterprise. Revenue has been growing, and the company has embraced AI, signaling adaptability. There are both fundamental and technical tailwinds behind the current surge, including these three factors. -
Revenue Growth Turning Profitable Growing top-line sales is important, but eventually that growth must translate into profits—especially after seven years as a public company. Upwork has begun converting sales into profits and is showing strength across several key areas. The company has beaten top- and bottom-line expectations, margins reached a record 29.6%, and the all-important Gross Services Volume (GSV) returned to growth in Q3 2025, up 2% year-over-year. During the Q3 conference call, Upwork raised full-year revenue and EBITDA guidance and highlighted its AI advances, which leads to our next point. -
Embracing AI, Not Being Replaced by It Many analysts expected generative AI to be an existential threat to freelance marketplaces like Upwork, where many tasks are one-off gigs companies might try to replace with models such as ChatGPT or Gemini. Instead, Upwork has embraced AI for hybrid workflows. Clients can now combine human freelancers with specialized AI agents for complex projects, and AI-based GSV has grown more than 50% year-over-year. The company also introduced UMA, its "work companion," to help freelancers and clients find each other more efficiently. -
Technical Trends Point to Additional Upside Fundamentals can take time to show up in a stock price if technical tailwinds aren't in place. Upwork now combines record sales, expanding margins, and improving technical indicators. The stock briefly sent mixed signals when the price dipped after a Golden Cross formed on the 50-day and 200-day simple moving averages (SMAs). 
The Golden Cross wasn't wrong—just early. The 50-day SMA wobbled but held as support, and the stock quickly broke back above the 2025 high it hit in September. The Relative Strength Index (RSI) is elevated but still below the overbought threshold of 70, suggesting there may be more upside to come. 2 Reasons to Be Bearish on UPWK in 2026 2025 performance aside, investors are most interested in what happens in 2026. For those considering a position in UPWK, here are two risks to watch. -
Shrinking Volume of Small Gigs AI has been a boon to overall revenue growth, but it has also exposed vulnerabilities. While GSV is growing, smaller jobs—those paying $300 or less—are eroding as companies increasingly turn to generative AI instead of hiring one-time freelancers to avoid onboarding. If Upwork concedes these smaller gigs to AI or competitors like Fiverr International Ltd. (NYSE: FVRR), the marketplace could shrink in GSV terms even if higher-value jobs remain plentiful. -
Broader Labor-Market and Integration Risks The macro picture looks stable for now: the Federal Reserve lowered rates again this month, and lower rates often help small-cap stocks with real cash flow and reasonable valuations. Still, the labor market is the canary in Upwork's coal mine, and the company's Enterprise segment (which serves large professional clients) has shown signs of weakness this year. Upwork's new Lifted platform for Enterprise clients is expected to require substantial integration work, which could reduce margins by roughly 2% in 2026. Margin stagnation combined with a slowing job market—or a recession—would likely reverse Upwork's profit gains and weigh on the stock. Investors should watch GSV trends, the health of the Enterprise segment, and how well Upwork continues to monetize AI-enabled workflows as they evaluate the company heading into 2026.
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