EP 37: How to Build a Successful Career in Law: Insights from Dina Segal, CLO of Gusto

Dina Segal is the Chief Legal Officer at Gusto, where she leads legal, compliance, and government affairs for a platform serving over 400,000 small businesses across the United States. In this episode, Dina shares her journey from growing up in Ukraine—where she was inspired by her grandfather’s work as a lawyer advocating for his community—to building a diverse legal career across BigLaw, fintech, and high-growth technology companies.We dive into her path through tax, litigation, and FCPA work during the 2008 financial crisis, her transition into corporate law, and her move in-house—where she ultimately rose into executive leadership roles at companies like Intuit before becoming CLO at Gusto.This conversation covers:- How to successfully transition from BigLaw to in-house- What it takes to grow into a Chief Legal Officer role- Why understanding the business is critical for in-house lawyers- How to approach career pivots with a “learning mindset” -Building and scaling legal, compliance, and government affairs teams- How AI is transforming legal workflows, decision-making, and team capacityDina also shares practical advice on promotions, leadership, and why the best lawyers today are not just advisors—but builders embedded within the business.If you’re a law student, practicing attorney, or operator working closely with legal teams, this episode offers a clear look at how modern legal careers are evolving—and what it takes to stay ahead.“Every change is a combination of intentionality and a leap of faith.”A great reminder that careers aren’t planned—they’re built.