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Additional Reading from MarketBeat.com 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 outcomes for those companies have been mixed. Many meme stocks have never come close to their 2021 highs and currently sit well below their peak levels. One of those former high-flyers is Upwork Inc. (NASDAQ: UPWK), the online gig marketplace that went public in 2018. Upwork appeared to be in danger of penny-stock status before COVID-19, then shares climbed from roughly $6 to about $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 under $10 per share shortly after the Fed began raising rates, and that run looked, in hindsight, like a fever dream. But now Upwork is once again rising, and this time the roughly 30% gain is driven 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 continues to climb, 2025 could be remembered as the year the company evolved into a mature tech-sector enterprise. Revenue is growing, and the company has embraced AI, signaling longer-term adaptability. There are both fundamental and technical tailwinds behind the move, including these three factors. -
Revenue Growth Turning Profitable It's one thing to grow top-line sales; eventually those sales must 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 areas. Not only has the company beaten 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. During the Q3 conference call, Upwork raised full-year revenue and EBITDA guidance and highlighted its AI progress, which leads to our next point. -
Successfully Mitigating AI Headwinds Many analysts expected generative AI to pose an existential threat to freelance marketplaces like Upwork, where many tasks are one-off gigs that could theoretically be handled by ChatGPT or Gemini. Instead of losing clients, Upwork has embraced AI and integrated it into hybrid workflows. Companies can now combine human freelancers with specialized AI agents for complex projects, and AI-based GSV has grown more than 50% year-over-year. The company also launched 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. Upwork now combines record sales, margin expansion, and constructive 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 was not wrong — it was just early. The 50-day SMA wobbled but held as support, and the stock quickly reclaimed the 2025 high it hit in September. The Relative Strength Index (RSI) is elevated but still below the overbought threshold of 70, which suggests there may be more upside to come. 2 Reasons to be Bearish on UPWK in 2026 Putting 2025's gains aside, investors are rightly focused on what may happen in 2026. If you're considering a position in UPWK, watch these two risks closely. -
Shrinking Gig Volume Is a Red Flag AI has helped lift Upwork's overall revenue, but it has also exposed vulnerabilities. GSV is up overall, yet smaller jobs — generally those paying $300 or less — are disappearing as companies increasingly turn to generative AI to avoid onboarding costs and time. If Upwork cedes these smaller gigs to AI or to rivals like Fiverr International Ltd. (NYSE: FVRR), the marketplace could contract in GSV even if higher-value jobs remain plentiful. -
Broader Labor Market Weakness The macro backdrop for Upwork is currently stable: the Federal Reserve lowered rates again this month, and lower rates often benefit small-cap stocks with positive cash flow and reasonable valuations. Still, the labor market is a canary in the coal mine for Upwork, and the company's Enterprise segment (which serves large professional clients) has already shown some weakness this year. Additionally, the 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 jobs market or a recession would likely reverse Upwork's profit momentum and put pressure on the stock.
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