Upwork’s Strategic Embrace of AI Could Push the Stock to $25, According to Experts!

Importantly, competition is not just limited to freelance marketplaces. Tech giants are eyeing the online talent space through an AI lens as well. LinkedIn (Microsoft), for instance, is leveraging generative AI across its platform – from smarter job recommendations to AI-written profile summaries. Microsoft has massive data on professionals and is integrating AI co-pilots into LinkedIn for hiring solutions. While LinkedIn’s freelance offerings (like ProFinder or Services Marketplace) are relatively nascent, Microsoft’s push could make LinkedIn a powerful AI-powered hiring ecosystem for both full-time and contract work. This means Upwork and Fiverr not only compete with each other, but must keep an eye on big tech entrants who are “sharpening their edge” with AI. In response, Upwork’s strategy is to innovate faster – continuing to roll out personalized AI tools, improving onboarding and matching, and even launching advisory councils on the future of AI and work. (Indeed, in 2025 Upwork formed an Economic Advisory Council with MIT/Stanford experts to study AI’s impact on labor – a thought leadership move to reinforce its role in this transformation.)