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For Your Education and Enjoyment 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 mixed outcomes. Most 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; shares then surged from $6 to $58 over 18 months. Elon Musk's Starlink project is generating major speculation ahead of a potential IPO that some analysts believe could reach a historic $100 billion valuation. According to James Altucher, there may be a smart "backdoor" way for everyday investors to position ahead of that event without needing traditional IPO access — and he says it can be done for under $100. He's also sharing a free ticker tied to this trend for anyone who wants to take a closer look. Click here to learn more UPWK fell back below $10 shortly after the Fed began raising rates, making that run feel 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 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 long-term adaptability. There are fundamental and technical tailwinds behind this surge, including these three factors. -
Revenue Growth Becoming Profitable Growing top-line sales is important, but eventually sales need to turn into profits—especially after seven years as a public company. Upwork has begun doing that, showing growth across several key areas. The company has beaten 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. On its Q3 conference call, Upwork raised full-year revenue and EBITDA guidance and highlighted its AI advances, which leads to the next factor. -
Successfully Mitigating AI Headwinds Many analysts expected generative AI to be a kill shot for freelance marketplaces like Upwork—after all, many tasks are one-off gigs companies could theoretically source from ChatGPT or Gemini. Instead of losing clients, Upwork embraced AI for hybrid workflows. Companies can now combine human freelancers and 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 if technical tailwinds aren't present. Upwork currently combines record sales, margin expansion, and favorable technical signals. The stock briefly sent mixed messages when the price dipped despite a Golden Cross forming between 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 reclaimed the 2025 high set in September. The Relative Strength Index (RSI) is elevated but still below the overbought threshold of 70, suggesting there may be more upside. 2 Reasons to be Bearish on UPWK in 2026 2025 performance aside, investors want to know what happens in 2026. For those considering a position in UPWK, here are two risks to watch. -
Shrinking Gig Volume Is a Red Flag AI has helped Upwork's overall revenue, but it has also introduced cracks. While GSV is growing overall, smaller jobs paying $300 or less are evaporating as companies increasingly use generative AI instead of hiring one-time freelancers to avoid onboarding costs. If Upwork cedes these smaller gigs to AI or competitors like Fiverr International Ltd. (NYSE: FVRR), the marketplace could see GSV contract again—even if higher-level projects remain plentiful. -
Broader Labor Market Weakness At the moment, the macro backdrop for Upwork appears stable. The Federal Reserve has lowered rates recently, and lower rates often benefit small-cap stocks with real cash flow and reasonable valuations. Still, the labor market is the canary in Upwork's coal mine: the company's Enterprise segment, which serves large professional clients, has already shown some weakness this year. Additionally, the company's new Lifted platform for Enterprise clients is expected to require substantial integration work, which could shave roughly 2% off margins in 2026. Margin stagnation combined with a slowing job market—or a recession—would likely reverse Upwork's profit growth and put pressure on the stock.
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