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Today's Featured 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 more mixed fate. Most (if not all) meme stocks never came close to their 2021 highs and now sit in the market's backwater. One of those former high-flyers is Upwork Inc. (NASDAQ: UPWK), the online gig marketplace that went public in 2018. Upwork looked headed for penny-stock status before the COVID-19 surge, when shares jumped from about $6 to roughly $58 over 18 months. With Donald Trump back in the White House, many believe an economic revival could be underway — but it also brings new risks for retirement savers. Traditional 401(k)s and IRAs may leave investors more exposed than they realize.
That's why a Trump-backed IRS strategy is gaining attention. It allows everyday Americans to reposition their retirement savings into real assets like gold and silver — offering both protection and potential upside. A new 2025 Wealth Protection Guide explains exactly how it works. Claim your FREE 2025 Wealth Protection Guide now Of course, UPWK fell back below $10 a share after the Federal Reserve began raising rates, and the whole run looked like a fever dream. Now Upwork is once again climbing, and this time the roughly 30% gain appears driven by more than just easy money. Can the stock sustain this momentum as we enter 2026? Here are three reasons to be bullish and two reasons to be cautious. 3 Reasons to be Bullish on UPWK in 2026 If Upwork's momentum holds, 2025 may be remembered as the year the company transitioned into a more mature tech-sector enterprise. Revenue has accelerated, and the company has embraced AI, signaling adaptability. Several fundamental and technical tailwinds are behind this surge, including the following. -
Revenue Growth Becoming Profitable Growing top-line sales is one thing; converting that growth into consistent profit is another — especially after seven years as a public company. Upwork has started turning revenue into profit and is showing gains across multiple areas. The company has been beating consensus on both revenue and earnings, margins reached record levels (29.6%), and the key Gross Services Volume (GSV) metric 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 brings us to the next point. -
Successfully Mitigating AI Headwinds Many analysts feared generative AI would hollow out freelance marketplaces by replacing one-off gigs with automated tools. Instead, Upwork has embraced AI for hybrid workflows. Clients can combine human freelancers with specialized AI agents for complex projects, and AI-driven GSV has grown more than 50% year-over-year. The company also launched UMA, a "work companion" designed to match freelancers and clients more efficiently. -
Technical Trends Point to More Upside Fundamentals can take time to show up in a stock price without confirming technical tailwinds. UPWK has both: record sales, expanding margins, and improving technical indicators. The stock briefly sent mixed signals 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 simply early. The 50-day SMA wobbled but held as support, and the stock quickly cleared the 2025 high set in September. The Relative Strength Index (RSI) is elevated but still below the overbought threshold of 70, which suggests there may be additional upside. 2 Reasons to be Bearish on UPWK in 2026 Putting 2025 behind us, investors are focused on 2026. If you're considering a position in UPWK, watch these two risk factors closely. -
Shrinking Gig Volume Is a Red Flag AI has helped overall revenue growth, but it has also exposed vulnerabilities. While GSV is growing, smaller jobs (roughly $300 or less) are disappearing as companies increasingly rely on generative AI instead of hiring one-time 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 contract again even if higher-value projects persist. -
Broader Labor Market Weakness At the moment the macro backdrop is stable: the Federal Reserve cut rates again this month, and lower rates generally help small-cap stocks that generate cash flow and trade at 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 shown signs of softness this year. Moreover, Upwork's new Lifted platform for Enterprise customers will require significant integration work, which management expects could shave roughly 2% off margins in 2026. Margin pressure combined with a slowing job market — or a recession — could reverse Upwork's profit gains and weigh on the stock.
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