Dr. Gleb Tsipursky – The Office Whisperer
Nirit Cohen – WorkFutures
Angela Howard – Culture Expert
Drew Jones – Design & Innovation
Jonathan Price – CRE & Flex Expert
In the most recent episode of The Allwork.Space Future of Work® Podcast, we spoke with Dave Bottoms, SVP of Product and GM of Marketplace at Upwork, to discuss how AI is transforming the largest talent platform in the world.
Drawing on two decades of experience leading product teams at Meta, Dropbox, and Yahoo, he explained how Upwork is moving beyond a simple job board into an intelligent ecosystem powered by AI.
The Pandemic, Distributed Work, and AI: A Perfect Storm
According to Bottoms, the transition to distributed work was accelerated by the pandemic and remains a dominant trend.
“COVID and distributed work became much more the norm,” he said.
Post-pandemic, companies continue to navigate between remote, hybrid, and office models. Meanwhile, AI innovation has exploded in the last two years.
Bottoms describes this as “one of the mega trends of the last couple of years.” This convergence led Upwork to rethink how they serve both clients and freelancers. They aimed to get in front of that and understand what AI could do to improve the platform experience.
From Job Boards to AI-Powered Talent Marketplaces
Upwork’s goal is clear: evolve from a simple marketplace where jobs are posted and freelancers bid to a sophisticated platform where AI helps find the right talent faster and smarter. He said he wanted to start “evolving Upwork from a talent marketplace to a place where you can find AI talent for projects that you want to hire.”
AI is helping automate and enhance several traditional tasks like writing job posts and matching talent.
Bottoms emphasized, “We’re really focused with our use of AI in sort of getting better about the match and getting clients able to hire the right person at the right time.”
This includes giving freelancers AI-powered tools to write stronger proposals based on years of data from successful bids.
UMA: Upwork’s Mindful AI Companion
A key innovation is UMA, short for Upwork’s Mindful AI. It began as a simple assistant to help with job posts and proposals but is evolving into an agent that can actively manage workstreams. Bottoms says it might actually do the sourcing for you and bring you back the best candidates for a job that you post.
UMA also supports real-time meetings by transcribing discussions, tracking agreements on milestones, pricing, and deadlines. These get packaged into usable contracts that help clients and freelancers stay aligned.
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“UMA is kind of evolving more into the agentic realm, like that agent that sits on your shoulder,” Bottoms said.
The Rise of Complex and Fractional Work
Upwork supports everything from simple hourly gigs to multi-person, multi-month projects. Bottoms observes an increasing demand for more complex projects that involve collaboration among diverse specialists.
He notes that the platform is changing to focus on higher-value work that brings together multiple skill sets to deliver sophisticated outcomes.
Fractional roles are another growing trend. Seasoned experts like fractional CFOs or CTOs can consult for multiple companies on flexible contracts. Freelancing gives them the freedom to design their work-life balance and select projects that match their skills and interests.
A New Model for Global Talent and Compliance
Upwork gives companies access to talent from around the world while respecting local laws and client preferences. Some clients prefer hiring only within certain regions, like the U.S., and the platform allows filtering by location. Freelancers go through identity checks to ensure reliability and compliance.
This approach helps businesses find the right skills globally while freelancers maintain flexibility in how and where they work.
The Future of Work Is AI and Human Creativity
For Bottoms, the future is about combining human creativity with AI’s power to automate routine tasks and accelerate work.
“We believe in the human creativity and taste and touch and having the human in the loop to guide and steer the work,” he said.
At the same time, AI agents will handle autonomous tasks and speed up delivery.
Upwork is investing heavily in AI and custom models to enhance matching and project management. Bottoms sees a future where “you’re going to be able to do things in two days that you used to do in two months or two weeks.”
Rather than reducing work, this extra capacity will allow people to focus on strategic and creative projects that push innovation forward. He says he doesn’t subscribe to the portion of that future where we become a leisure society, and that there’s always more work than we have capacity to do.
The platform’s mission is clear: to unlock human potential through AI and create a more efficient, flexible, and creative future of work.
