Two companies merge to make Upwork, the leader in online freelancing

It’s basic entrepreneurialism: two brands saw a hole in the market and sought to fill it. How they combined their strengths to help Upwork claim its place as an industry trailblazer

Supply and demand principles have dictated much of Brian Levey’s professional life. As an eight-year-old hocking collectibles at baseball card conventions and as a Federal Reserve Board employee working to decrease stock market volatility, those principles are the common thread binding Levey’s career. His current post is no different. As general counsel and chief financial officer at Upwork, an online freelancing platform, Levey is helping solve a common supply and demand equation: connecting independent professionals with the companies that need them.

“Our goal is to make markets more efficient and to empower people on a global scale,” says Levey. “We connect the global demand for talent with the global supply of talent. It’s no coincidence that I ended up here.”

Levey joined Upwork at a critical time for the company. In 2013, after a 13-year stint as a senior leader of eBay’s legal team, he left to serve as GC for oDesk, an Upwork predecessor. A year later, oDesk merged with Elance, another freelancing platform, and Levey took the legal helm of the combined company. In 2015, Elance-oDesk rebranded itself to form Upwork, launching a new platform that aims to quickly connect freelance workers (software developers, graphic designers, writers, and other professionals) with paying clients. Levey stayed on as general counsel, and in June 2015, he was also named CFO—a role that allows him to make streamlined, risk-based decisions to benefit the entire company.

“Just like eBay was a pioneer in facilitating the sale of global goods, Amazon revolutionized retail, and iTunes transformed music, I see Upwork as a pioneer in creating a new way for people to work.”

That’s a lot of change for one business to weather, but Levey says his team navigated through the pain points of integration by focusing on the evolution of Upwork’s brand. Merging companies is never easy, of course, and competitors that combine forces present an even greater challenge. In many ways, the Elance-oDesk partnership was “like the Red Sox and the Yankees agreeing to merge,” Levey said. But the launch of a new platform allowed them to combine the best aspects of each company and drop the worst.

“Merging during a period of growth is always much easier than integrating companies that are shrinking,” he says. “It creates a lot of runway to bounce around ideas and develop new skills. It was a great opportunity to start from scratch, and we got to take the best from both companies, both culturally and from a sheer user experience perspective.”

From a leadership perspective, Levey says the transformation helped recalibrate his team’s mission and steadied its focus on helping Upwork take a growing segment of the market. Likewise, the merger-rebrand allowed Upwork to become a more customer-centric platform.

“We’re a two-sided market: clients on one hand and independent professionals on the other,” says Levey. “This [merger] allowed us to take a fresh, new look at how we’re serving both sides.”

As a whole, Upwork is throttling towards success in the freelance marketplace. The company’s platform cumulatively has more than 10 million registered freelancers—the largest freelancing site based on freelancer earnings. Upwork is playing in a market segment estimated to reach in excess of $20 billion by 2020, according to one staffing industry report, up from an estimated $3 billion in 2014. But don’t lump it in with the rest of the “gig economy.”

“I don’t think of our platform as a ‘gig’ platform,” Levey said. “Rather, we’re making it easier for highly skilled and knowledge-based workers to enjoy a more flexible lifestyle. We’re responding to a need that exists, and we’re enabling opportunities.”

In doing so, he adds, the company aims to rival the entrepreneurial achievements of its Silicon Valley forefathers. “Just like eBay was a pioneer in facilitating the sale of global goods, Amazon revolutionized retail, and iTunes transformed music, I see Upwork as a pioneer in creating a new way for people to work,” Levey says. “I’ve learned that it doesn’t make sense to be number two or three at anything in the business world.”