Brian Levey Believes That Connections Are Critical

Chief Business Affairs and Legal Officer Brian Levey aims to act as Upwork’s chief problem solver as well, eliminating conventional blind spots across the company

Brian Levey, Chief Business Affairs and Legal Officer, UpworkPhoto: Russ Jang

Brian Levey has taken the Upwork mission to heart. A global hiring platform with hundreds of thousands of active customers in more than 180 countries, Upwork connects businesses around the world with talented freelance professionals seeking new work opportunities. And as chief business affairs and legal officer at Upwork, Levey spends his days ensuring that his team members are connected to the business, but also to each and every other team at the company.

Since the beginning of his legal career, Levey says, he has been conscious of the negative opinions that many people have of attorneys. Traditionally, attorneys have been seen as roadblocks, as disciplinarians, or as individuals often in conflict with the businesses they work for. But Levey has always sought to turn those perceptions on their head.

“I have always been interested in the business side, in problem solving and enabling, as well as the legal side,” says the attorney, who majored in economics and completed a short stint at the Federal Reserve Board before transitioning into law school and the legal sector. “In the Upwork legal department, we have our own mission, which is to enable, accelerate, and protect the Upwork business in a collaborative and innovative manner.”

As Levey explains, the Upwork legal department is the department of “how” instead of the department of “no” because he and the other legal team members use a relationship-based approach to solving problems with the business units, using tools like AdvanceLaw’s feedback mechanism, to improve performance and constantly strive to avoid traditional, unproductive legal approaches. The team’s accomplishments have earned it several notable legal industry recognition awards.

Often, he says, this strategy comes down to asking questions like, “How can we avoid the ‘Chicken Little the-sky-is-falling’ approach? How can we avoid the ivory tower academic approach when looking at business issues?”

“How can we avoid the ‘Chicken Little the-sky-is-falling’ approach? How can we avoid the ivory tower academic approach when looking at business issues?”

Levey and his team have come up with their own unique answer to those questions. “We like to use a sort of Mick Jagger approach with our business partners,” Levey says with a chuckle. “We always say, ‘You can’t always get what you want, but we’ll give you what you need.’”

But it’s not just the legal team’s performance that Levey wants to optimize—he helps teams all over the company fulfill their potential by “connecting the dots” across those teams and the legal team to further the company’s best interests.

“We assign a legal liaison to be the primary point of contact for most of the business teams and primary company initiatives to reduce the ‘blind spots’ amongst various functions that affect all companies,” he explains. “That allows us to better ensure that our business partners have the tools they need to succeed—which hopefully speeds up decision-making, results in more informed decisions and fewer surprises, and increases trust.”

Levey’s commitment to keeping Upwork’s teams connected to each other and to its global footprint of users is key to the company’s day-to-day success, especially given the remote knowledge work performed via the Upwork website between the various professionals and businesses that use Upwork’s platform: as Levey notes, approximately 97 percent of all Upwork transactions are negotiated and conducted between third-party users who are located at least fifty miles apart, a testament to how the Upwork site provides new opportunities to those living outside major cities.

“Talent is everywhere, and we’re trying to unlock potential in more places than ever before.”

This approach has proven especially critical during the major transitions the company has seen since its initial public offering (IPO) in 2018. “We’re obviously on a larger stage now,” Levey says of those changes. “We need to raise the bar every day for what is expected of us, and try to leverage the recent IPO to create more credibility with businesses who are looking to use our website.”

“But we’re still essentially operating the same way,” Levey continues. “We still do the right thing. We still prioritize and invest in legal compliance across the business—and ultimately try to use compliance as a competitive advantage.”

In other words, Levey says, Upwork’s core business and core values have not changed—just the scale at which Levey and his teams are expected to enable those opportunities for skilled professionals on a global basis. “Talent is everywhere, and we’re trying to unlock potential in more places than ever before,” he remarks. “And when you’re doing things that have never been done before, the work is really fast-paced and we have to be nimble.”

Fortunately, Levey feels he and his team are more than up to that challenge. “I’ve always loved solving problems in a collaborative and relationship-based way. I like to think of myself not just as Upwork’s chief business affairs and legal officer but, along with the rest of the legal team, act as its chief problem solver as well,” he says.

Unlocking Opportunity

Recently appointed to the US Securities and Exchange Commission’s Small Business Capital Formation Advisory Committee, Brian Levey revels in the opportunity to leverage his experience with public companies, his passion for marketplaces, and his yearning to provide more economic opportunities so people have better lives.

“I’ve always been passionate about making inefficient markets more efficient,” Levey says. “Both Upwork and eBay [where Levey served as a legal executive for thirteen years prior to joining Upwork in 2013] are first-of-their-kind marketplaces that have helped unlock economic opportunities for businesses of all sizes around the world, and I’m trying to facilitate the same thinking on the Commission’s Advisory Committee, especially for Main Street investors.”