Article | 5 min read

Work it: A CX Moment with Upwork

Zendesk chatted with Upwork’s Vice President of Customer Support, Brent Pliskow, about the evolving workplace landscape and the growing need for freelancers.

By Meaghan Murphy, Contributing Writer

Published November 3, 2022
Last updated November 3, 2022

With unemployment at a near 50-year low, many American companies have struggled to find highly skilled workers. Finding—and keeping—talent is an ongoing challenge for many businesses. And with the number of Americans who quit their jobs at a 20-year high, companies are increasingly relying on independent contractors from across the globe.

Upwork is the world’s largest work marketplace where companies can find independent talent to grow their businesses, and independent talent can find work to grow their careers. The company’s revenue has increased steadily since 2016, reaching more than $502 million in 2021. Upwork was also named one of Time’s 100 most influential companies of 2022.

As part of Zendesk’s CX Moment virtual event series, we spoke with Upwork’s Vice President of Customer Support, Brent Pliskow, about the changing needs of American businesses and the international freelance talent they hire.

The future workforce

According to Upwork’s annual Future Workforce Report, businesses are struggling to source talent. More than two-thirds of hiring managers say they’ll need to fill positions over the next six months—and those managers are having a difficult time finding skilled workers for those roles. As a result, more hiring managers are turning to freelance workers.

“The nature of work has changed significantly over the past few years, and that also means that the nature of temporary work has changed,” Pliskow explains. “We’ve really gotten away from this idea of temporary work as being a stopgap.”

One big advantage of hiring freelancers is that those workers can be located anywhere in the world, allowing businesses to cast a wide net for talent.

“What they’re looking for is that skilled-talent workforce, which they might not be able to find within their local city or region,” Pliskow says. “So, they’re now turning to the global workforce to see what talent and skills may be available.”

“The nature of work has changed significantly over the past few years, and that also means that the nature of temporary work has changed. We’ve really gotten away from this idea of temporary work as being a stopgap.”Brent Pliskow, Vice President of Customer Support at Upwork

Upwork’s global reach has even allowed the company to support workers who have been displaced by the ongoing war in Ukraine. “Individuals who are finding themselves in very severe predicaments have the opportunity to carry forward and still support their livelihoods by utilizing our platform and continuing their [freelance] careers,” says Pliskow.

While businesses are using Upwork to find new talent around the world, workers who may feel stuck in their regular 9-to-5 jobs have the opportunity to explore new career paths.

“There are opportunities for them to tap into skills that were previously unearthed or tucked away that they wanted to bring forward and say, ‘You know what? I actually think my passion is somewhere else,’” Pliskow says. “On the Upwork platform, they can find many different opportunities from great businesses around the world in order to build their skill set.”

Successful CX

Upwork practices what it preaches when it comes to customer service—many of its CX agents are freelancers.

“What better way to support our customers—who are utilizing the same platform—than to have people that live and breathe and experience that day-to-day?” asks Pliskow. “In their interactions with our customers, they’re saying, ‘Hey, I’m a freelancer on this platform, too. I really can empathize with what you’re experiencing right now—like, truly empathize with it.’”

And even though Upwork’s CX agents receive 600,000 tickets annually, the team seems to be happy. The voluntary turnover rate is less than 5 percent.

“We’re keeping them engaged,” Pliskow says of his agents’ success. “And I think that the best thing that we’re doing is ensuring that we are communicating effectively across the board. They are part of the Upwork family.”

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Using technology to connect

While Upwork uses Zendesk to connect with customers and simplify workflows, it also relies on other technology platforms to support its business. Pliskow says unitQ has been effective in providing customer insights.

“It allows us to get early detection of issues that are surfacing within our environment,” explains Pliskow. “It even allows us to identify the long-standing issues in our environment so that we can carry that forward and influence any product stakeholders.”

Upwork also uses Forethought for AI-based CX. “We are heavily investing in technology that’s going to enable our agents to be more efficient, more effective, and really uplevel the customer experience,” Pliskow says. “58 percent of the interactions that come through our chatbot experience are resolved, leaving only 42 percent of that population to be handled by our support team.”

The human touch

While Upwork relies on AI for things like log-in questions and other basic queries, Pliskow’s team strives to find a balance between automation and humanity.

“AI technology—probably in our lifetime—will never get to a point of being able to handle [a situation] where human touch and involvement is required,” says Pliskow. “In the case of disputes, we’re entering the conversation with the client and the talent, and we are becoming an empathetic third party to what’s going on—and helping them steer the way to a resolution.”

The culture at Upwork also encourages initiative from all its human workers—even those who aren’t currently on staff.

“One of the benefits of having [an, in part,] freelancer workforce is you’re bringing in talent with a very diverse background—in experience and cultures and everything else,” says Pliskow. “Every agent within our team is encouraged to put forward ideas that would benefit our customer base as well as the agent experience. If theirs have been pulled forward and implemented, they’re rewarded in kind for that contribution. It just reinforces the innovation that we bring to the platform by having talent sourced from within.”

Missed our chat? Watch the on-demand event with Upwork’s Brent Pliskow.

Get the popcorn

Join us for more expert-led CX sessions. Check out our upcoming virtual events.

Get the popcorn

Join us for more expert-led CX sessions. Check out our upcoming virtual events.

Register for free