Evolving with Jessica Nguyen

The legal industry is changing fast, and the best legal and business leaders aren't waiting for permission to evolve. Evolving with Jessica Nguyen is the podcast for in-house legal professionals who are thinking bigger. Every episode, Jessica sits down with legal and business leaders who are future-proofing their teams to go deep on how they hire, how they lead, how they're using AI, and what they're still figuring out. From AI tools and legal technology to leadership, mentorship, and building modern legal departments, this show covers what it really takes to build a legal team and company that's ready for whatever comes next. If you're an in-house lawyer, general counsel, or legal operations professional who's excited about where the legal profession is going, this show is for you. Evolving with Jessica Nguyen, brought to you by Sandstone. Learn more at sandstone.com.

Episodes

Alexandra Sepulveda: Curiosity is a Superpower

September 30, 2026 • 54 mins

What do duct-taped ramen floaties have to do with in-house counsel? Everything, according to Alexandra Sepulveda, who has learned that curiosity, receipts, and the willingness to start over are the real survival skills of a legal career. Jessica sits down with Alexandra Sepulveda of Trust & Will for a wide-ranging conversation about building a legal career across startups, enterprise, and everything in between. They cover ment...

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Dina Segal: Build, Iterate, Transform

September 16, 2026 • 54 mins

Every general counsel remembers the job they didn't want. For Dina Segal, that job became the foundation for every one that followed, and the reason she now tells rising leaders to stop waiting until they feel ready. Jessica sits down with Dina Segal, Chief Legal Officer of Gusto to talk about her path from early litigation and tax work to becoming CLO, and what she has learned about building fearlessness, hiring for AI fluency, a...

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Trista Engel and Jessica Markowitz: Think Like an Executive

September 2, 2026 • 69 mins

Two non-lawyers now run one of the legal industry's most established staffing firms, and their outsider perspective may be exactly what makes them so valuable to the GCs they serve. Jessica sits down with Trista Engel, CEO, and Jessica Markowitz, President and Chief Operating Officer of Paragon Legal. Together they trace how two business partners without legal backgrounds built Paragon into a national flexible legal talent company...

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Deborah Solmor on Preparing the Next Generation of GCs

August 19, 2026 • 53 mins

Deborah Solmor spent two decades as a Skadden litigator before walking into her first General Counsel role and discovering that being a lawyer was, as she puts it, the least interesting thing about the job. Her journey from big law to nonprofit GC became the foundation for a mission bigger than any single title. In this episode, Jessica sits down with Deborah Solmor, General Counsel of Wisconsin Alumni Research Foundation and Foun...

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Catherine Romero: Always Bet on Curiosity

July 8, 2026 • 54 mins

Some careers follow a straight line. Catherine Romero's is not one of them, and that is exactly what makes it worth talking about. In this episode, Jessica sits down with Catherine Romero, a former manager, mentor, and dear friend who quietly left an engineering career at Boeing, secretly enrolled in law school, helped take Amazon public at Perkins Coie, and is now back in an engineering role at Microsoft using AI to help solve so...

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Mary O'Carroll on Bridging Law and Technology

July 8, 2026 • 40 mins

Mary O'Carroll is one of the most influential voices in legal operations, and for good reason. She has spent two decades building, connecting, and pushing the industry forward. In this episode, Jessica sits down with Mary O'Carroll, CEO of LegalEng Consulting Group, for a wide-ranging conversation on where legal ops came from, where legal tech is going, and what it is going to take to get there. Episode Threads How CLOC start...

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Eric Dodson Greenberg on Relationships and the Future of Law

July 8, 2026 • 71 mins

Twenty years into a legal career, the question worth asking is not what you know but how you learned it. Eric Dodson Greenberg has a few stories about that. Evolving with Jessica Nguyen is officially here. Jessica sits down with Eric Dodson Greenberg, EVP, General Counsel & Corporate Secretary of Cox Media Group, for a conversation that covers career growth, leadership culture, and where AI is taking the legal profession. Whe...

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Evolving with Jessica Nguyen Trailer

June 16, 2026 • 2 mins

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Evolving with Jessica Nguyen

Episodes

.css-14f5ked{margin:0;word-break:break-word;display:-webkit-box;-webkit-box-orient:vertical;box-orient:vertical;-webkit-line-clamp:2;overflow:hidden;}Alexandra Sepulveda: Curiosity is a Superpower

.css-r6mb8g{margin:0;word-break:break-word;display:-webkit-box;-webkit-box-orient:vertical;box-orient:vertical;-webkit-line-clamp:1;overflow:hidden;}Dina Segal: Build, Iterate, Transform

Trista Engel and Jessica Markowitz: Think Like an Executive

Deborah Solmor on Preparing the Next Generation of GCs

Catherine Romero: Always Bet on Curiosity

Mary O'Carroll on Bridging Law and Technology

Eric Dodson Greenberg on Relationships and the Future of Law

Evolving with Jessica Nguyen Trailer

Popular Podcasts

Alexandra Sepulveda: Curiosity is a Superpower

Dina Segal: Build, Iterate, Transform