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Today's Exclusive News Can Upwork Maintain Its Comeback? Reasons to Be Bullish and BearishSubmitted by Dan Schmidt. 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 those companies 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 former high-flier 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 jumped from about $6 to roughly $58 over 18 months. However, UPWK fell back under $10 shortly after the Fed began raising rates, and that entire run felt like a fever dream. Now Upwork is again climbing, and this time the roughly 30% gain looks supported 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 for caution. 3 Reasons to be Bullish on UPWK in 2026 If Upwork keeps ascending, 2025 may be remembered as the year the company matured into a tech-sector enterprise. Revenue is growing, the company has embraced AI, and there are both fundamental and technical tailwinds behind the rally. Here are three key factors. -
Revenue Growth Turning Profitable Growing revenue is one thing; turning revenue into profits is another — especially for a company that's been public for several years. Upwork has begun converting sales into profit and is showing growth across several key areas. 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 initiatives, which leads to the next point. -
Successfully Mitigating AI Headwinds Many analysts expected generative AI to hurt freelance marketplaces, since some one-off tasks could theoretically be replaced by models like ChatGPT or Gemini. Instead, Upwork has embraced AI and integrated it into hybrid workflows. Companies can hire human freelancers alongside specialized AI agents for complex projects, and AI-based GSV has grown more than 50% year-over-year. Upwork also launched UMA, a "work companion" designed to help freelancers and clients connect more efficiently. -
Technical Trends Point to More Upside Solid fundamentals can take time to show up in a stock's price if technical tailwinds aren't present. Upwork now combines record sales, margin expansion, and encouraging technical signals. The stock sent mixed signals when the price briefly dropped after a Golden Cross formed between the 50-day and 200-day simple moving averages (SMAs).  The Golden Cross wasn't wrong — it was simply early. The 50-day SMA wobbled but held as support, and the stock quickly moved back above the 2025 high set in September. The Relative Strength Index (RSI) is elevated but still below the overbought threshold of 70, suggesting there could be further upside. 2 Reasons to be Bearish on UPWK in 2026 Performance in 2025 is encouraging, but investors should consider what might derail the story in 2026. Here are two risks to watch. -
Shrinking Gig Volume Is a Red Flag AI has helped Upwork's overall revenue, but it has also exposed vulnerabilities. GSV is growing overall, yet smaller jobs paying $300 or less are disappearing as companies increasingly turn to generative AI instead of onboarding one-time freelancers. If Upwork cedes these smaller gigs to AI tools or competitors like Fiverr International Ltd. (NYSE: FVRR), the marketplace could contract in GSV even if higher-end projects remain available. -
Broader Labor Market Weakness The macro backdrop is relatively stable today: the Federal Reserve has cut rates recently, and lower rates often benefit small-cap stocks with healthy 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. Additionally, Upwork's new Lifted platform for Enterprise clients is expected to require substantial integration costs that could reduce margins by roughly 2% in 2026. Margin stagnation combined with a slowdown in the job market, or a recession, would likely reverse Upwork's profit progress and put downward pressure on the stock.
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