The department of how: Brian Levey’s legal leadership lessons from eBay and Upwork

In this episode of The Legal Leaders Podcast, host David Lancelot talks with Brian Levey, Senior Advisor at Upwork and former Chief Legal Officer and Chief Business Affairs Officer, about scaling high-growth businesses, building high-trust legal teams, and how modern in-house lawyers become true business leaders. 

Brian shares lessons from helping scale eBay during its early hypergrowth – from 900 employees and $400M in revenue to a global powerhouse – and later building the legal function at Upwork, one of the world’s largest freelancer marketplaces. Throughout the conversation, he explains how legal leaders can embed themselves within the business, prioritize the risks that truly matter, and create systems that allow companies to scale without slowing innovation. 

They discuss: 

• How legal leaders help scale companies during hypergrowth 
• Building a high-trust legal team and culture 
• Moving from the “department of no” to the “department of how” 
• Creating frameworks that allow legal teams to prioritize risk and enable the business 
• Why modern in-house lawyers must become business partners, not just advisors 

Tune in for an unfiltered conversation on scaling businesses, building high-trust teams, and becoming a true partner to the business as a legal leader.