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Today's Bonus News 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 recall the meme-stock era of 2021, but the companies involved have had mixed fortunes. 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. The company looked in danger of penny-stock status before COVID-19, when shares surged from about $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 Of course, UPWK fell below $10 per share shortly after the Fed began raising rates, making the earlier run feel like a fever dream. But now Upwork is once again rising — roughly a 30% gain fueled by more than just cheap money. Can the stock sustain this momentum as we enter 2026? We've got three reasons to be bullish, and two reasons to remain cautious. 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 bona fide tech-sector enterprise. Revenue has been growing, and the company has embraced AI, signaling long-term adaptability. There are both fundamental and technical tailwinds behind the recent surge, including these three factors. -
Revenue Growth Becoming Profitable It's one thing to grow top-line sales; eventually those sales need to translate into profits, especially after seven years as a public company. Upwork has begun converting revenue into earnings 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 the all-important Gross Services Volume (GSV) metric returned to growth in Q3 2025, up 2% year-over-year (YOY). During the Q3 conference call, Upwork raised full-year revenue and EBITDA guidance and highlighted its AI advances — which leads us to the next factor. -
Successfully Mitigating AI Headwinds Many analysts and investors expected generative AI to be a potential "killshot" for freelance marketplaces like Upwork, where many tasks are one-off gigs that companies could theoretically source from ChatGPT or Gemini. Instead of siphoning off clients, Upwork embraced AI for hybrid workflows. Clients can now combine human freelancers with specialized AI agents for complex projects, and AI-based GSV has grown more than 50% YOY. 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 also in place. Upwork now has the combination of record sales, margin expansion, and encouraging technical signals. The stock 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 — it was just early. The 50-day SMA wobbled but ultimately held as support, and the stock quickly reclaimed the 2025 high it notched in September. The Relative Strength Index (RSI) is elevated but still below the overbought threshold of 70, suggesting there could be more upside to come. 2 Reasons to be Bearish on UPWK in 2026 Looking past 2025, investors are focused on what might happen in 2026. For those considering a position in UPWK, here are two headwinds to watch. -
Shrinking Gig Volume Is a Red Flag AI has helped drive Upwork's overall revenue growth, but it's also exposed vulnerabilities. GSV is growing overall, yet smaller jobs — those paying $300 or less — are evaporating as companies increasingly turn to generative AI instead of hiring one-off freelancers to avoid onboarding. If Upwork cedes these smaller gigs to AI or to competitors like Fiverr International Ltd. (NYSE: FVRR), the marketplace could see GSV shrink again — even if higher-value jobs remain available. -
Broader Labor Market Weakness The macro picture for Upwork is currently stable: the Federal Reserve has lowered rates recently, and lower rates often benefit small-cap stocks with solid cash flow and reasonable valuations. But the labor market is the canary in the coal mine for Upwork, and the company's Enterprise segment (which serves large professional clients) has shown signs of weakness this year. Additionally, the company's new Lifted platform for Enterprise clients is expected to carry substantial integration costs that could shave roughly 2% off margins in 2026. Margin stagnation combined with a slowdown in hiring — or a recession — would likely reverse Upwork's profit gains and could weigh heavily on the stock.
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