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

Upwork’s positioning vs Fiverr skews more towards technical and professional services and enterprise clients. Upwork’s AI integration is deeply baked into core marketplace functions (search, job posting, hiring workflow), and it spans over 250 skill categories including software development, data science, and AI engineering – domains where Upwork traditionally has strength. While Fiverr has a high volume of quick-turnaround gigs, Upwork tends to facilitate larger or longer-term projects (its average client spend is several times higher than Fiverr’s). Thus, Upwork’s “AI Work Agent” approach (Uma) is tailored to speeding up multi-step hiring processes and managing complex projects (even assembling “optimal teams of experts” for a project, as Uma can now do). Fiverr’s AI, conversely, leans toward creative collaboration tools. Both firms share the philosophy that AI should help, not hurt, freelancers: Fiverr’s marketing explicitly reassures that humans remain at the center, and Upwork similarly emphasizes human-AI collaboration (Uma’s name even stands for a mindful assistant). However, Upwork appears to be ahead in directly embedding AI into user workflows at scale – evidenced by the high opt-in rates for its AI features and the fact that a majority of new job posts on Upwork are now AI-assisted. Upwork also partnered with enterprise tech players (OpenAI, Microsoft via Azure OpenAI services, etc.), signaling to big corporate clients that it’s serious about providing top-tier AI talent and tools.