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This Week's Exclusive Story Can Upwork Maintain Its Comeback? Reasons to Be Bullish and BearishAuthored by Dan Schmidt. First 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 fortunes of those companies are mixed. Most — if not all — have never come 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 destined for penny-stock status before COVID-19, then shares jumped from roughly $6 to about $58 over 18 months. The #1 memecoin for the new year
With the market oversold and a potential new year rally just around the corner, this could be one of the most explosive opportunities of the new year. Get the #1 memecoin for January 2026 here. Of course, UPWK fell below $10 per share after the Fed began raising rates, making the earlier run feel like a fever dream. But now Upwork is rising again — a roughly 30% gain driven by more than 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 keeps rising, 2025 may be remembered as the year it matured into a solid tech-sector company. Revenue is growing and the company has embraced AI, signaling adaptability. These fundamental and technical tailwinds include the following three factors. -
Revenue Growth Turning Profitable Growing top-line sales is one thing; eventually those sales must convert into profits, especially after seven years as a public company. Upwork has begun doing that and is showing gains across several key areas. The company has been beating top- and bottom-line expectations, margins have reached a record 29.6%, and the all-important Gross Services Volume (GSV) metric returned to growth in Q3 2025, up 2% year-over-year. In the Q3 conference call, Upwork raised full-year revenue and EBITDA guidance and highlighted its AI progress, which leads to our next point. -
Successfully Mitigating AI Headwinds Many analysts and investors expected generative AI to be a kill shot for freelance marketplaces like Upwork, where many tasks are one-off gigs that companies could theoretically source from ChatGPT or Gemini. Instead of losing clients, Upwork embraced AI for hybrid workflows. Companies can now hire human freelancers alongside 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 More Upside Strong fundamentals can take time to show up in a stock price without matching technical momentum. Upwork now combines record sales, expanding margins, and encouraging technicals. At one point the share price fell even after a Golden Cross formed between the 50-day and 200-day simple moving averages (SMAs), which sent mixed signals to investors. 
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 may be more upside to come. 2 Reasons to be Bearish on UPWK in 2026 Putting 2025 performance aside, investors are focused on what will happen in 2026. For anyone considering a position in UPWK, here are two risks to watch. -
Shrinking Gig Volume Is a Red Flag AI has been a boon to Upwork's overall revenue growth, but it has also introduced a few cracks. While total GSV is growing, smaller jobs — roughly $300 or less — are evaporating as some companies opt for generative AI rather than one-off freelancers to avoid onboarding. If Upwork cedes these smaller gigs to AI or competitors like Fiverr International Ltd. (NYSE: FVRR), the marketplace could see GSV shrink again even if higher-level jobs remain plentiful. -
Broader Labor Market Weakness At the moment the macro picture for Upwork looks stable. The Federal Reserve lowered rates again this month, and lower rates often benefit small-cap stocks that have 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. Additionally, Upwork's new Lifted platform for Enterprise clients is expected to require substantial integration costs, which could shave about 2% off margins in 2026. Margin stagnation combined with a slowdown in the job market — or a recession — would likely reverse Upwork's profit growth and pressure the stock.
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