The Department of How: What modern legal leaders can learn from eBay and Upwork
Brian Levey doesn’t talk about legal the way most lawyers do. At Upwork, where he spent more than a decade as the company’s top attorney (as well as a two-and-a-half-year stint as its CFO), he didn’t think of his team as a control function, or a final checkpoint before decisions were made.
He called them something else entirely. “The Department of How.”
Not the department of no – with the metaphorical police stick, stepping in at the last minute to shut things down – but the team people came to when they needed to figure out how to move forward.
It’s a small shift in language, but it reveals something much bigger about how Levey sees the role of legal. Because in fast-moving companies, whether scaling eBay in its early days or building a global talent marketplace like Upwork, the question is rarely whether something should be done. The real question is how to do it well, how to do it safely, and how to do it in a way that helps the business move faster and with more clarity.
That mindset didn’t come from theory. It was shaped over years of operating inside companies that were growing faster than any legal function could keep up with if it stayed reactive. From eBay’s early expansion, when the company grew from hundreds of employees into a global giant, to Upwork’s challenge of connecting millions of talent marketplace users across more than 180 countries, Levey was constantly faced with the same reality: legal couldn’t sit on the sidelines.
It had to be part of how the business worked.
From legal expertise to business impact
Levey’s path into law wasn’t driven by a lifelong ambition to practise. If anything, it was shaped by curiosity about business. How decisions get made, how markets move, how value is created.
That thread runs through everything he talks about. Even early in his career, working in private practice, something didn’t quite sit right. “I learned at the law firm, I don’t want to write the memo,” he says. “I want to be the one making the decision.”
It’s a simple line, but it captures a shift many in-house lawyers recognize. The difference between advising from the outside and operating from within. Between producing analysis and living with outcomes.
Moving in-house gave him that proximity. But more importantly, it changed what mattered.
“Understanding the business at a deeper level is the most important asset any in-house attorney can bring to the table.”
Not legal brilliance in isolation. Not perfectly drafted memos. But context – real, grounded understanding of how the business works.
That’s what allows legal to contribute in a different way. Not as a function that reviews decisions after the fact, but as one that helps shape them in the first place.
Scaling legal without slowing the business
Of course, thinking this way is one thing. Making it work at scale is another.
When Levey was VP & Deputy General Counsel in charge of the corporate legal function at eBay Inc (which, at that time, also included PayPal) and later at Upwork, he found himself operating in environments where growth was relentless. New markets, new products, new risks – often all at once. In that kind of setting, a traditional legal model quickly becomes a bottleneck.
The question becomes unavoidable: how do you support a business that’s moving this fast without slowing it down?
For Levey, the answer wasn’t working harder. It was working differently. “We live in a world of limited resources,” he explains. “How can we prioritize what we do? How can we allow the business to be more self-sufficient and really focus on the company’s higher magnitude and higher probability risks?”
That thinking led to a deliberate shift. Legal couldn’t, and shouldn’t, be involved in everything. Instead, it needed to focus on the work that truly mattered and create the conditions for the rest to happen without it.
You get a sense of how real that challenge was when Levey reflects on his early in-house experience. Coming out of private practice, he remembers writing long, carefully considered memos only to wonder whether anyone was reading them, or whether they were making any difference at all.
That moment – quiet, almost unremarkable – captures the gap he was trying to close. The distance between producing legal work and having real impact on the business. It’s the gap that forces a different approach.
At Upwork, that meant building systems. Templating the repetitive work so teams didn’t have to start from scratch each time. Creating triage frameworks so effort was directed where it mattered most. Embedding legal into parts of the business, such as sales, so issues could be spotted early rather than escalated late. And increasingly, using tools to reduce friction and free up time.
Over time, something interesting happened. The business became more confident operating on its own. Legal became more focused. And the relationship between the two shifted from dependency to partnership.
There was, as Levey puts it, a kind of predictability to it. The business knew when to bring legal in. And just as importantly, it knew when it didn’t need to.
The trust quotient of great legal leaders
Underpinning all of this is something less tangible, but arguably more important. Trust.
Levey describes it through the lens of the trust quotient, a framework he first heard about at a legal leaders’ conference. The concept was documented in a book, The Trust Advisor (published in 2000), and it is a way of thinking about credibility, reliability, and how comfortable people feel engaging with you, balanced against self-interest.
The idea resonated with Levey, who states, “trust is the moat.”
You can see what he means in practice. When trust is high, legal is brought into conversations early. Not as a blocker, but as a sounding board. Teams are more open about risks. Leaders are more willing to share uncertainty. Things move faster. Not because risk disappears, but because it’s understood.
When trust is low, the opposite happens. Legal becomes something to work around. Conversations happen later, under pressure, often when options are already limited. The difference isn’t technical ability. It’s how people experience working with you.
And trust, as Levey is quick to point out, isn’t built in big moments. It’s built in the small ones. Through consistency. Through what he describes as the “say-do ratio” – the alignment between what you say and what you do.
It’s also shaped by how leaders show up for their teams. “People stay when they feel trusted, not managed,” he says.
That kind of environment doesn’t just feel better to work in. It performs better.
A shift defined by relationships, not titles
Spend enough time listening to Levey, and one thing becomes clear. For all the frameworks and operating models, what he values most isn’t the structure. It’s the people.
The most satisfying part of it all, he reflects, isn’t just building businesses, but “seeing these folks elevate themselves, elevate their careers, and just keeping in touch with folks. It’s all about those relationships, that trust built in the trenches.”
That idea sits quietly underneath everything else. Because scaling legal, embedding teams, designing systems, none of it works without that foundation. You can build the best processes in the world, but if the business doesn’t trust you, they won’t use them. If your team doesn’t feel trusted, they won’t stretch into the roles you need them to play.
And that’s really where the shift in legal leadership happens. Not in org charts or reporting lines, but in proximity. In being close enough to the business to understand it. Close enough to your team to support them. Close enough to the work to anticipate what’s coming next.
Over time, that changes what success looks like. Not how many matters you’ve touched. Not how often you’ve been right. Not how visible legal is across the organization. But the impact you’ve had on the moments that matter.
Or, as Levey puts it, “it’s all about slugging percentage, not batting average.”
It’s a way of thinking that frees legal leaders from trying to be everywhere at once. Instead, it focuses attention where it counts – on the decisions that shape outcomes.
And it changes the conversation with the business. Because in the end, the question isn’t whether legal is involved. It’s how. Not “Can we do this?” But “How can we problem solve to accelerate the business?”
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