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Today's Featured Content 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 poorly. Most—if not all—have never come close to their 2021 highs and currently languish 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, then shares soared from about $6 to $58 over an 18-month stretch. What No One's Saying About Amazon's 30k Layoff
First they cut jobs at Meta... now 30,000 at Amazon – its largest layoff in history. What's happening inside these Mag 7 companies, particularly as the stocks continue to soar to all- time highs? The same former hedge fund manager who predicted the dot com crash, the housing crisis and the fall of Lehman is now stepping forward to explain what's really going on... and what you should be doing with your money Learn more. UPWK fell back under $10 a share shortly after the Fed began raising rates, making the earlier run feel like a fever dream. But now Upwork is soaring again, and this roughly 30% gain is backed by more than just easy money. Can the stock sustain this momentum as we head into 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 keeps climbing, 2025 may be remembered as the year the company transitioned from a growth-stage platform into a more mature tech-sector enterprise. Revenue has been rising and the company has embraced AI, signaling adaptability. There are both fundamental and technical tailwinds behind this surge; here are three key factors. -
Revenue Growth Turning Into Profitability It's one thing to grow top-line sales; after seven years as a public company, those sales need to convert into profits. Upwork has started doing that. The company has been beating top- and bottom-line expectations, margins have reached record levels (29.6%), and 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 progress—setting the stage for the next tailwind. -
Successfully Mitigating AI Headwinds Many expected generative AI to be a killshot for freelance marketplaces, since some one-off tasks can be handled by models like ChatGPT or Gemini. Instead, Upwork has folded AI into hybrid workflows. Companies can hire human freelancers alongside specialized AI agents for complex projects, and AI-related GSV has grown more than 50% year-over-year. The company also introduced 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 without supporting technicals. Upwork now has the combination of record sales, expanding margins, and improving technical indicators. The stock sent mixed signals earlier when price dipped even 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 held as support, and the stock quickly reclaimed its September 2025 high. The Relative Strength Index (RSI) is elevated but still below the overbought threshold of 70, suggesting room for further gains. 2 Reasons to be Bearish on UPWK in 2026 Putting 2025 performance aside, investors are focused on what might happen in 2026. If you're considering a position in UPWK, watch these two risk areas. -
Shrinking Gig Volume Is a Red Flag AI has helped Upwork's revenue, but it has also introduced vulnerabilities. While overall GSV is growing, smaller jobs—those paying $300 or less—are disappearing as companies increasingly turn to generative AI rather than hiring one-off freelancers to avoid onboarding. If Upwork cedes these lower-value gigs to AI or rivals like Fiverr International Ltd. (NYSE: FVRR), the marketplace could see GSV shrink again even if higher-level work remains available. -
Broader Labor Market Weakness The macro picture looks relatively stable today: the Federal Reserve has recently cut rates, and lower rates tend to benefit small-cap names with healthy cash flow and reasonable valuations. Still, the labor market is a canary in Upwork's coal mine. The company's Enterprise segment—which serves large professional clients—has already shown signs of weakness this year. Additionally, the new Lifted platform for Enterprise clients is expected to require substantial integration costs, which could trim margins by roughly 2% in 2026. Margin stagnation coupled with a slowdown in the job market—or a recession—would likely reverse Upwork's recent profit gains and weigh on the stock.
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