Future 50
A New Generation of Leaders Arrives

For leading the world’s largest freelance-work platform

When Hayden Brown became Upwork’s CEO in January, she informally assumed another role: a chief steward of The Project Economy. 

The future of work is filled with freelancers—and organizations will need them to execute ambitious initiatives with speed and agility. But the future is also filled with uncertainty. So Brown is focused on building a smarter, more strategic workforce. Last year, Upwork’s platform facilitated US$2.1 billion of project work—more than 85 percent from “large engagements and complex projects,” Brown told investors in February. 

“Today, the top question we get [from businesses] is how they can use our solution. They recognize the need to evolve their talent strategy and want to know how to get started,” she said.

With nearly a third of Fortune 500 companies using Upwork, Brown is doing more than matching troubleshooters to tasks. Her goal is to build a pipeline that fortifies teams executing high-value projects with sustainable muscle. To that end, the company sliced its freelance talent pool from 2.6 million to roughly 800,000—part of Brown’s plan to better align its offerings to what clients actually need.

She took that client-first approach a step further in April, allocating US$1 million to selected organizations working on projects to battle coronavirus. Upwork’s Work Together Talent Grants Program matched organizations with skilled independent professionals to help develop and accelerate projects with a mission tied directly to alleviating COVID-19’s damage to individuals, communities and economies.

“We all face a common challenge—mobilizing our resources to mitigate the devastating impact of this virus on our communities and economy,” Brown said. “This challenge requires us to work quickly and at scale across a broad range of skills and with fresh thinking.”