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Just For You Can Upwork Maintain Its Comeback? Reasons to Be Bullish and BearishReported by Dan Schmidt. Date Posted: 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 remember the 2021 meme-stock era fondly, but the reality for those companies is mixed. Most 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 looked like it might revert to penny-stock status before COVID-19, then shares surged from roughly $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 back under $10 shortly after the Federal Reserve began raising rates, making that run feel like a fever dream to many investors. 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 have three reasons to be optimistic — and two reasons to remain cautious. 3 Reasons to be Bullish on UPWK in 2026 If Upwork's run continues, 2025 may be remembered as the year the company graduated into a more mature tech-sector business. Revenue growth and an embrace of AI suggest the company is adapting for the long term. There are both fundamental and technical tailwinds behind the rally, including these three factors. -
Revenue Growth Turning into Profitability Growing top-line sales is important, but after seven years as a public company, investors want to see profits. Upwork has started converting sales into profits and is showing improvement across several key metrics. The company has beaten top- and bottom-line expectations, margins reached a record 29.6%, and Gross Services Volume (GSV) returned to growth in Q3 2025, up about 2% year-over-year. During the Q3 conference call, management raised full-year revenue and EBITDA guidance and highlighted its AI progress, which ties into the next point. -
Mitigating AI Headwinds Successfully Many analysts feared generative AI would hollow out freelance marketplaces by replacing one-off gigs. Instead, Upwork has leaned into AI and created hybrid workflows: companies can combine human freelancers with AI agents for complex projects. That approach appears to be working — AI-driven GSV grew more than 50% year-over-year, and the company launched UMA, a "work companion" designed to connect freelancers and clients more efficiently. -
Technical Trends Point to More Upside Strong fundamentals don't always translate to an immediate stock-price move without supportive technicals. Upwork currently has a constructive mix: record sales, expanding margins and improving technical indicators. The stock briefly sold off even after a Golden Cross formed 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 held as support, and the stock moved back above its 2025 September high. The Relative Strength Index (RSI) is elevated but still below the overbought threshold of 70, suggesting there may be room to run. 2 Reasons to be Bearish on UPWK in 2026 Putting 2025 performance aside, investors are focused on 2026. If you’re considering a position in UPWK, watch these two risks. -
Shrinking Small-Gig Volume Is a Red Flag AI has helped overall revenue, but it has also exposed vulnerabilities. While GSV is growing, smaller jobs (around $300 or less) are declining as companies increasingly use generative AI instead of hiring one-off freelancers to avoid onboarding costs. If Upwork loses these smaller gigs to AI or to competitors such as Fiverr International Ltd. (NYSE: FVRR), the marketplace could see GSV shrink even if higher-value projects remain available. -
Broader Labor-Market Weakness The macro backdrop is currently favorable — the Federal Reserve has eased policy recently, which often helps small-cap stocks with real cash flow. Still, the labor market is the canary in Upwork's coal mine. Upwork's Enterprise segment, which serves large professional clients, has shown signs of weakness this year. Moreover, the new Lifted platform for Enterprise clients will likely require significant integration costs, which management expects could shave roughly 2% off margins in 2026. Margin stagnation coupled with a slowing job market or a recession would likely reverse Upwork's profit momentum and could pressure the stock.
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