Finally, Upwork’s own efforts to court investors may help – the company has been more vocal in telling its “AI transformation” story. In 2023–2024, CEO Hayden Brown frequently discussed how generative AI is not a threat but a tailwind for Upwork’s business – because it drives more companies to seek freelance talent and more freelancers to upskill (a theme echoed by independent research). Upwork even established an economic advisory council in 2025 to explore the future of AI and work, signaling to the market that it’s at the forefront of these changes. This thought leadership can translate into greater investor confidence that Upwork will seize the opportunities AI presents.
Conclusion: Upwork’s stock around ~$13–$15 in mid-2025 appears to many analysts as a mispriced asset, given the company’s return to growth, improving profitability, and strong positioning in a secular uptrend (the shift to freelance and AI-powered work). Achieving a $25 share price would likely require a continuation of current performance – e.g., delivering on quarterly numbers, raising full-year guidance perhaps, and showing that AI integrations (like Uma) are translating into higher client spend and freelancer success. If those boxes are ticked, a re-rating is very plausible. In essence, the market is starting to recognize that Upwork is transforming from a volatile “gig economy” play into a more mature platform with operating leverage and a unique role in the future of work. As one report succinctly put it: “Upwork’s AI-first pivot and record Q1 profits give it the edge in the freelance platform race.” With edges like that, the stock may well edge higher – and $25 could be a stepping stone rather than a ceiling if the company executes its vision in the coming years.
