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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 tell a different story. Most meme stocks have never come close to their 2021 highs and currently sit in the market's dustbin. One former high-flyer is Upwork Inc. (NASDAQ: UPWK), the online gig marketplace that went public in 2018. Upwork appeared in danger of penny-stock status before the COVID-19 surge; shares then climbed from about $6 to $58 over 18 months. Some AI researchers believe the next phase of artificial intelligence could arrive as early as 2026 — and that it may accelerate innovation far faster than previous breakthroughs.
In a recent briefing, a veteran technology analyst explains what artificial general intelligence is, why leading AI executives see it as a major inflection point, and which areas of the market he believes could benefit as development advances. Watch the briefing here After the Federal Reserve began raising rates, UPWK fell back under $10, and that prior run started to look like a fever dream. But Upwork is soaring again, and this recent roughly 30% gain reflects 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 for caution. 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 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 revenue; it's another to convert it into profit — especially after seven years as a public company. Upwork has begun doing the latter and is showing improvement across several key metrics. The company has been beating top- and bottom-line expectations; margins reached a record 29.6%, and the all-important Gross Services Volume (GSV) returned to growth in Q3 2025, up about 2% year-over-year. During the Q3 conference call, Upwork raised full-year revenue and EBITDA guidance and highlighted its AI progress, which leads to the next factor. -
Successfully Mitigating AI Headwinds Many expected generative AI to be a killshot for freelance marketplaces like Upwork, since many one-off tasks could theoretically be handled by ChatGPT or Gemini. Instead, Upwork embraced AI and enabled hybrid workflows: companies can hire human freelancers alongside specialized AI agents for complex projects. According to the company, AI-based GSV has grown more than 50% year-over-year. Upwork also introduced UMA, its "work companion," to help freelancers and clients connect more efficiently. -
Technical Trends Point to More Upside Strong fundamentals sometimes take time to show up in a stock price if technical tailwinds aren't aligned. This stock now has a mix of record sales, margin expansion, and encouraging technical signs. Shares briefly dropped even after a Golden Cross formed on the 50-day and 200-day simple moving averages (SMAs), which sent mixed signals to some investors. 
The Golden Cross wasn't wrong — it was early. The 50-day SMA wobbled but held as support, and the stock quickly reclaimed its 2025 September high. 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 Setting 2025 performance aside, investors are 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 vulnerabilities. While GSV is growing overall, smaller jobs — generally those paying $300 or less — are evaporating as companies increasingly use generative AI instead of hiring one-time freelancers to avoid 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-level projects remain plentiful. -
Broader Labor Market Weakness The macro picture is currently stable: the Federal Reserve recently lowered rates again, and lower rates often help small-cap stocks with strong 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 weakness this year. Additionally, Upwork's new Lifted platform for Enterprise clients is expected to require substantial integration costs, which could shave roughly 2% off margins in 2026. Margin stagnation combined with a slowing job market — or a recession — could reverse Upwork's recent profit gains and pressure the stock.
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