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Today's Bonus Article 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 had a more mixed fate. Most — if not all — meme stocks never came 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 appeared headed toward penny-stock status before COVID-19, then surged from about $6 to $58 over 18 months. REVEALED: America just unlocked a $500 trillion asset
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One company is already in position and this could be one of the most important AI infrastructure plays heading into 2026. The name and ticker are available here now >>> Of course, UPWK fell back below $10 a share shortly after the Fed began raising rates, and that whole run started to look like a fever dream. But now Upwork is once again rising, and this time the roughly 30% gain is supported by more than just easy monetary policy. 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 its ascent, 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 over the long term. Several fundamental and technical tailwinds underpin the current surge, including these three factors. -
Revenue Growth Becoming Profitable Growth alone isn't enough — sales must eventually translate into profits, especially after seven years as a public company. Upwork has begun converting revenue into profit and is showing growth across several key metrics. 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 about 2% year-over-year. On the Q3 conference call, Upwork raised its full-year revenue and adjusted EBITDA guidance and highlighted AI-related progress, which leads to the next factor. -
Successfully Mitigating AI Headwinds Many analysts expected generative AI to be a threat to freelance marketplaces like Upwork, since some one-off tasks could theoretically be handled by ChatGPT or Gemini. Instead, Upwork has leaned into AI for hybrid workflows. Clients can now combine human freelancers with 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 if technical tailwinds aren't in place, but UPWK now has the combination of record sales, expanding margins, and improving chart patterns. Shares sent mixed signals when the price dipped briefly despite a Golden Cross forming between the 50-day and 200-day simple moving averages (SMAs). 
The Golden Cross wasn't wrong — it was just early. The 50-day SMA held as support, and the stock quickly reclaimed and moved above the 2025 high set in September. The Relative Strength Index (RSI) is elevated but still below the overbought threshold of 70, suggesting room for additional upside. 2 Reasons to be Bearish on UPWK in 2026 Putting 2025 performance aside, investors are rightly focused on 2026. If you're considering a position in UPWK, watch these two risks. -
Shrinking Gig Volume Is a Red Flag AI has helped boost Upwork's overall revenue, but it has also exposed structural vulnerabilities. While GSV is growing, smaller jobs paying $300 or less are rapidly disappearing as companies increasingly use generative AI instead of hiring one-time freelancers to avoid the time and cost of onboarding. If Upwork cedes these 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 available. -
Broader Labor Market Weakness The macro backdrop is relatively stable for now: the Federal Reserve has cut rates recently, and lower rates often benefit 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. Additionally, the company's new Lifted platform for Enterprise clients will likely require substantial integration costs, which could reduce margins by roughly 2% in 2026. Margin stagnation combined with a slowdown in the jobs market — or a recession — could reverse Upwork's profit gains and put significant pressure on the stock.
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