Building AI-powered experiences for humans—with Upwork’s Brent Pliskow

Since its inception, Upwork has unlocked economic opportunity by empowering its global network of freelancers to break free from the traditional workday, set their own schedules, and live better lives.

Within the company’s support organization, this same entrepreneurial spirit guided the team’s early adoption of AI as they looked to provide better experiences for their user base and internal teams.

“We are risk takers,” said Brent Pliskow, GM and VP of Customer Support at Upwork. “We build and break fearlessly, so with that value in mind, we didn’t have too many roadblocks to get off and on our way.”

One year into their AI integration and the team is already seeing exciting metrics, including a 20 percent increase in self-service rates and an overall rate that continues to climb month after month.

“What our customers wanted was answers quickly and they didn’t want to wait in a queue,” said Pliskow. “They didn’t want to wait in a backlog for information that was going to help them unlock their experience and get on their way.”

For the team, this means rethinking their whole approach to service, including how they delineate between the roles of AI and human agents.

“How can we translate our service offering so that when you engage with an agent, there’s extreme value provided in that experience?” said Pliskow. “One where the customer isn’t just coming for a question response, but for a more meaningful conversation to hopefully drive that customer outcome even further.”

We dive into that question and more, including what it means to have an “AI adjacent” strategy and how the Upwork team is paying down its experience debt on the latest episode of Conversations with Zendesk.

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