CEO of freelance platform Upwork shares how she’s helping the next generation build a freelance career and avoid burnout

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Hayden Brown, president and CEO of Upwork Courtesy of Upwork
  • Upwork is a platform connecting companies with freelancers to transform businesses.
  • Hayden Brown, president and CEO, shared how she navigated the company through the pandemic.
  • Brown also detailed Upwork’s plans to support the next generation of freelance and contract workers.
  • This article is part of a series about CEOs and their vision for the future called “What’s Next.”

At Upwork, working from home is not a new phenomenon.

The freelancer platform calls itself the “world’s work marketplace,” helping bridge companies and freelancers together. The practice of working from anywhere has been the company culture since its founding in 1998 when it was “Elance.” And founders, Beerud Sheth and Srinivas Anumolu were working out of an apartment in Jersey City, New Jersey. The company became Upwork in 2015.

Upwork has 539 corporate employees, 1,372 freelancer or contract workers, with workers in over 800 cities. The company’s revenue for 2020 was $373 million and freelancers with profiles on the platform earned $2.3 billion in 2020.

Pre-pandemic, most freelancers worked remotely, while employees in their physical offices had “Work from Home Wednesdays” available.

Hayden Brown became president and CEO in January 2020 after holding positions of senior vice president of product and design and chief marketing and product officer. Three months into her new leadership role, COVID-19 closed offices, but she saw it as an “opportunity.”

“It was really a moment to say, we’re going to leverage the strengths we have as a team that knows how to work remotely and do that really well,” she said. “And lean into my brand as the new CEO around communication, clarity, transparency, and amplify all of that at once and make sure everyone is hearing from me and our leadership team.”

In keeping with her commitment to communication and transparency, Brown, along with her leadership team, did weekly video calls to keep staff well-informed.

“As much as hindsight is 20/20, I don’t have something I wish we had done differently,” she said. “There were so many beautiful things that we were able to put together really quickly to help in the moment of crisis. So I’m not saying we did everything perfectly, but given what was happening, it’s hard to really go back and think, what could we have done [differently]?”

Avoiding burnout with freelancers and ‘synchronized time off’

The switch to remote work made workers more accessible to each other leading to a major rise in reports of burnout. Insider reported that compared to February 2020, workers are spending 2.5 times the minutes per week in meetings, sent 45% more chats per week to coworkers, and sent 42% more work chats outside regular business hours.

But Brown feels they’ve been able to avoid burnout using their “secret sauce” of utilizing freelancers to manage workloads.

Teams have a $500 freelance budget they can use on talent on their own platform to get stuff done and offload work. “We actually deliver that to our customers through freelancers and our platform, and we did that ourselves,” Brown said.

The other tactic Brown used is “synchronized time-off,” when the entire company (apart from customer support and similar functions) shut down. Over the 2021 Memorial Day weekend, Upwork employees had two extra days off.

The idea is when people come back “they’re not individually taking personal time off, but then their team was all working and they come back to this overflowed inbox,” she said.

Brown and her teams are also using tools, like Slack, Zoom, and Google Workspace, to improve communication and remove business divisions among teams.

Supporting young people as they join the work marketplace

Although Brown has never freelanced herself, she believes in the power it has to change people’s feelings about work and the economy.

Upwork conducted a study of the independent workforce in America and found 59 million Americans performed freelance work in 2020, an increase of 2 million freelancers since 2019.

Another key finding was the wave of Gen-Zers ages 18-22 who entered the job market. Over 36% of them started freelancing since the beginning of the COVID-19 pandemic, making them about half of the freelance workforce.

“The younger generations have seen that employment, the traditional employment contract, isn’t what it was in the past,” Brown said. “They want the autonomy to build their careers when, where, and how they can on their terms.”

Upwork plans to help the next generation by keeping the platform free and accessible while continuing to work with educational partners.

“People think freelancing is maybe not a serious career choice, and something they may not be able to do sustainably, which is not true,” Brown said. “We’re very focused on trying to pull the covers off of what’s really happening with the freelance economy, educate more businesses about the power and potential of [freelancing], and what they can do with the amazing skilled workers that are available through the platform.