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Today's Bonus Content 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 mixed fate. Most (if not all) meme stocks never came close to their 2021 highs and today sit far below those 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 surged from roughly $6 to $58 over 18 months. A growing number of investors are questioning how much of the market is now concentrated in just a handful of mega-cap stocks.
In a recent interview, a veteran investor discusses why this concentration matters, how he's structured his own portfolio to reduce reliance on Big Tech, and the framework he believes can deliver competitive returns with lower volatility across market cycles. Watch the full interview here Of course, UPWK fell back below $10 a share shortly after the Federal Reserve began raising rates, and that whole run came to seem like a fever dream. But now Upwork is once again rising, and this time the roughly 30% gain is driven by more than just easy money. Can the stock sustain this momentum as we enter 2026? We've got three reasons to be optimistic, and two reasons for caution. 3 Reasons to be Bullish on UPWK in 2026 If Upwork keeps climbing, 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 both fundamental and technical tailwinds behind this surge, including these three factors. -
Revenue Growth Turning 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 started converting sales into profits and is 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. During the Q3 conference call, Upwork raised full-year revenue and EBITDA guidance and highlighted its AI advances, which leads to the next point. -
Successfully Mitigating AI Headwinds Many analysts expected generative AI to be a threat to freelance marketplaces—work that used to go to one-off freelancers could theoretically be handled by ChatGPT or Gemini. Instead, Upwork embraced AI for 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 introduced UMA, a "work companion" designed 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 without supporting technical momentum. Upwork now has the combination of record sales, expanding margins, and encouraging technical signals. The stock sent mixed messages when the price dipped even after a Golden Cross formed 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 ultimately 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 room for further gains. 2 Reasons to be Bearish on UPWK in 2026 Putting 2025's results aside, investors are most concerned with what happens 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 Upwork's revenue growth overall, but it has also exposed vulnerabilities. GSV is growing, yet smaller jobs—those paying $300 or less—are rapidly disappearing as companies turn to generative AI instead of hiring one-off freelancers to avoid onboarding. If Upwork cedes these smaller gigs to AI tools or competitors like Fiverr International Ltd. (NYSE: FVRR), the marketplace could shrink in GSV terms even if higher-value projects remain available. -
Broader Labor Market Weakness The macro picture for Upwork currently looks stable: the Federal Reserve trimmed rates again this month, and lower rates often help small-cap stocks with solid cash flow and reasonable valuations. Still, 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. Plus, Upwork's new Lifted platform for Enterprise clients is expected to require substantial integration costs, which could shave roughly two percentage points off margins in 2026. Margin stagnation combined with a slowing job market—or a recession—would likely reverse Upwork's recent profit gains and pressure the stock.
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