At the epicenter of a rapidly transforming work landscape, Upwork has been leading an ambitious integration of generative AI into the heart of its marketplace. Dave Bottoms, GM Marketplace and SVP of Product at Upwork, described in an interview with me the organization’s journey as a decisive response to the disruptive emergence of ChatGPT at the end of 2022. Rather than approaching Gen AI as merely a tactical addition, Upwork saw it as a fundamental driver reshaping both talent productivity and the structure of work itself.
The company quickly established Upwork Labs, a dedicated experimental group tasked with identifying and implementing AI across its platform. A key early initiative was an AI-driven job post generator, a tool that automatically crafted optimized job postings using machine learning models. This innovation dramatically accelerated the hiring process by simplifying job post creation and enhancing discoverability, reflecting Upwork’s broader philosophy: use AI to eliminate friction without undermining the human element.
Internally, the Upwork engineering teams piloted GitHub Copilot to boost productivity, initially focusing on zero-to-one projects with minimal interdependencies. Over eighteen months, this cautious experimentation blossomed into adoption across nearly all teams. Developers embraced AI tools as productivity enhancers rather than job threats, transforming check-in rates, deployment velocity, and overall cycle times. Daily deployments, once an aspiration, became the new standard, improving scalability, reliability, and bug rates across the board.
Designers Step Into Production with Gen AI
Perhaps the most surprising development, Bottoms noted, is that designers—not just engineers—have begun producing production-level code through Gen AI tools. Upwork’s design teams, rooted in platforms like Figma, are now leveraging emerging features such as Dev Mode to export high-fidelity prototypes directly into code ready for deployment. This leap represents a fundamental shift: designers are no longer merely suggesting user experiences; they are building them.
The rise of this capability signals a profound evolution in the role of design. Traditionally, wireframes and mockups were translated into specifications that engineers would interpret. Now, designers can rapidly test, validate, and implement ideas without the intermediary step, dramatically accelerating product iteration cycles. The impact on productivity and creative agility is striking, with designers engaging in a level of technical execution previously reserved for engineers.
Alongside designers, product managers at Upwork are also experimenting with Gen AI to prototype and validate concepts faster than ever. The tools available today allow product thinkers to move from an idea to a functional demonstration in record time, setting a new tempo for innovation across the organization.
Balancing Productivity Gains with Workforce Anxiety
Despite the clear productivity advantages, Upwork acknowledges the anxiety that Gen AI adoption stirs among both internal teams and freelance talent on its platform. Developers initially worried about displacement are now largely reassured given Upwork’s focus on AI as a companion, not a competitor. True value remains rooted in understanding customer pain points, system architecture, and the nuanced application of technology—skills that no AI has yet mastered independently.
Among Upwork freelancers, similar shifts are underway. Categories like writing and translation have seen changes in human demand, as AI tools have automated many basic tasks. However, new opportunities have risen for those willing to adapt. Instead of straightforward translation, the platform now sees demand for local language experts who can fine-tune AI outputs to ensure cultural and linguistic authenticity. In writing, the emphasis is shifting toward editorial oversight, quality assurance, and SEO refinement rather than original content creation alone.
Bottoms emphasized that freelancers who master AI-enhanced workflows are not just surviving; they are thriving. They move up the value chain by increasing their project volume and ensuring higher-quality outcomes. In a sense, AI has expanded the definition of expertise itself, rewarding those who can both collaborate with machines and provide human judgment where it still matters most.
Charting a Future of Humans Plus AI
Looking ahead, Upwork’s vision is clear: the next three to five years will be defined by a powerful synergy between humans and AI. Upwork’s mindful AI, Uma, already powers smarter client-freelancer matching. But the ambitions go further. Bottoms envisions a future where not just humans, but agentic AI entities operate within the marketplace, acting on behalf of clients and freelancers alike.
Clients might one day deploy AI agents to search for talent, review freelancer proposals, and even collaborate on project management. Freelancers could have AI assistants finding jobs, preparing applications, and managing client communications. Upwork’s two-sided marketplace is poised to evolve into a richer, more complex ecosystem that remains deeply human but vastly more efficient.
Through it all, Upwork’s commitment to responsible AI use remains paramount. Rather than replacing humans, the company is empowering individuals to become more capable, more productive, and more valuable. As designers push into coding, as engineers deploy daily, and as product teams innovate faster than ever, one truth is emerging unmistakably: Gen AI is not just enhancing work at Upwork; it is fundamentally redefining it.
About the Author
Dr. Gleb Tsipursky was named “Office Whisperer” by The New York Times for helping leaders overcome frustrations with hybrid work and Generative AI. He serves as the CEO of the future-of-work consultancy Disaster Avoidance Experts. Dr. Gleb wrote seven best-selling books, and his two most recent ones are Returning to the Office and Leading Hybrid and Remote Teams and ChatGPT for Leaders and Content Creators: Unlocking the Potential of Generative AI. His cutting-edge thought leadership was featured in over 650 articles in prominent venues such as Harvard Business Review, Fortune, and Fast Company. His expertise comes from over 20 years of consulting for Fortune 500 companies from Aflac to Xerox and over 15 years in academia as a behavioral scientist at UNC-Chapel Hill and Ohio State. A proud Ukrainian American, Dr. Gleb lives in Columbus, Ohio.
