Upwork’s Hayden Brown has had a trial by fire, starting as CEO in January and navigating the freelancer marketplace through the pandemic.
Courtesy of Upwork
Just 66 days into her tenure as the CEO of Upwork, Hayden Brown was forced to shutter and decide whether to sublease the freelancing platform’s physical offices and comfort many of her 600 newly remote employees—all while fulfilling her promise to complete a company-wide listening tour and a report on the state of the business within her first 100 days.
“This is a year where you can’t BS your way through anything as a leader,” says Brown, who was named Upwork’s first female CEO in January. “I always was committed to transparency and frequent communication, and that was part of my leadership mantra and style starting in January.”
Amid millions of layoffs and turbulent markets, the 22-year-old company has rarely seen as much success as it has in the aftermath of the pandemic. With a market cap of $3 billion, Upwork (which went public in 2018) is now the world’s largest, public online freelance marketplace, primarily providing remote job listings. Its stock has surged, up roughly 70% year-to-date. In the last six months, the platform’s number of freelancer and corporate registrants has increased by 50%.
In September, Upwork released a study of the U.S. independent workforce, showing that 36% of the U.S. workforce freelanced during the pandemic—a 22% increase since 2019. Twelve percent of the country’s workforce started freelancing amid the pandemic. Covid also accelerated companies’ adoption of freelancers. The study found that nearly three quarters of hiring managers are continuing or increasing their usage of independent professionals.
Today, more than five million companies use Upwork to post freelancer job listings for a monthly fee starting at 3% of freelancer billing to clients, while freelancers can list their services for free and apply for remote jobs. They are charged a service fee of between 5% and 20%, depending on the total amount they’ve billed clients. In 2019, Upwork saw $300.6 million in revenue, up 83% over the last three years. And the company is on track to see more growth this year. On Wednesday, the company reported a year-over-year sales increase of 24%, and said they are on track to see roughly $365 million in revenue in 2020.
Brown attributes this success to pandemic-related trends. “People have shifted not just their notions about remote work in this moment of crisis, but also their long term views of how remote work will fit into their organizations,” she says.
And she intends to capitalize on it. In the past year, Brown has increased the company’s investment in a sales force focused on working with larger customers, including Microsoft, Airbnb and GE. Last year, more than 85% of Upwork’s $2.1 billion in gross services volume—or the total dollar value transacted through Upwork’s platform—was derived from large engagements and complex projects, not short-term gig work.
“The spend is actually going to projects that are long-term in nature. It’s large, complex work,” she says. “That’s where our customers are finding success. It’s not about these like small transactions or fly-by-night engagements.”
“We’ve doubled down on our values and our beliefs. And frankly, a lot of those have been aligned with some of the secular trends, such as remote work.”
Brown is no stranger to pivots. At age 12, her family moved from the small town of Amesbury, Massachusetts, to Kathmandu, Nepal. While her mom ran a Nepalese women’s empowerment program and her dad worked in community development, Brown studied at a small American school.
“Seeing the work my parents did was a huge inspiration for me in terms of dedicating your life to doing something that really has an impact on the world,” she says. “That led me to, through my adolescence and early career, seek out experiences where I could live and work in places very different, to be amongst other people and learn and challenge myself to have new perspectives.”
After graduating from Princeton in 2004 with a politics degree—and a short stint as an analyst at management consulting firm McKinsey & Company—Brown landed at Microsoft in 2007. Her focus was mergers and acquisitions strategy, and she cut her teeth working on high profile deals like Microsoft’s $45 billion Yahoo bid and $240 million Facebook investment.
But Brown yearned for more mission-driven work. After interviewing with more than 60 companies in the San Francisco Bay Area, in 2011 Brown took a job as a product director at 70-person startup Upwork (then called Elance-oDesk). Nearly a decade later, she’s running the place—at one of the most turbulent times in the company’s history.
“From the pandemic to Black Lives Matter to wildfires, it has been a year that has tested us in new ways,” she says. “We’ve doubled down on our values and our beliefs. And frankly, a lot of those have been aligned with some of the secular trends, such as remote work . . . We’ve been doing it for 20 years.”
One of Upwork’s biggest challenges has been convincing companies to rely on its remote freelance workers, Brown says. Now, that barrier has been broken.
An Upwork study found that as a result of Covid, nearly half of hiring managers are more likely to hire independent professionals in the future than they were prior to the crisis.
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“Whether you go back to work on a hybrid model or full-time, confidence in the productivity of remote work is unquestioned now,” says Ron Josey, a senior analyst at JMP Securities. “This pandemic has proven that you absolutely can work from home, and you can do so pretty effectively.”
However, Upwork isn’t the only company capitalizing on this trend. Gig work-focused platform Fiverr, whose stock has jumped an impressive 84% this year, is among the fastest-growing companies in the freelance space, Josey says. And freelancing platform Toptal, which has no headquarters and deems itself the “world’s largest fully remote company,” is on track to see more than 40% revenue growth this year, says its CEO, Taso Du Val.
But with its new focus on pairing long-term freelancers with large corporations, Upwork is differentiating itself from competitors, Josey says. Upwork has also invested in user experience, teaming up with software company Citrix in June to build a workspace so clients can more easily onboard the freelancers they find on its site.
What’s more, companies are also turning to Upwork to solve their intrinsic diversity issues. “I can’t tell you the number of CEOs I talked to who are thinking, ‘I have to solve the diversity challenge in my business, and remote work is one of the key tools,’” Brown says. “We have to let go of this very office-centric culture and incorporate people who are in a lot of geographies.”
Brown has implemented this practice herself, announcing on May 22 that Upwork employees will be given the option to work from home even after the pandemic is over.
“For society and for business, that’s only a good thing,” she says, “because it does open the doors for people to participate in the labor market in different ways.”
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