Afleveringen
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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 some of the world's biggest problems.
Episode Threads
How Catherine secretly enrolled in law school without telling her parents
Going from engineer to lawyer and back to engineer again
The work inside Microsoft's AI for Good team: a Vatican history project, a global weather model, and food security mapping with the UN
Why Catherine, having lived through PCs and the internet, is not afraid of AI
What Catherine noticed in Jessica's interview 13 years ago and what it says about standing out as a candidate
How to earn enough trust with a client that they invite you to join their team
The founding of IPLI and the story of one participant who made it to partner after spending years living in a car in the Bronx
What the legal profession needs from the next generation as AI reshapes entry-level work
Connect & Visit:
Catherine Romero
Jessica Nguyen
Evolving with Jessica Nguyen -
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 started as a lunch between people who had no name for what they did
What drove every move in Mary's career from Google to Ironclad to big law and back out
What a legal engineer is and the three skills that define one
Why big law genuinely wants to change but cannot easily walk away from what has made it successful
What AI-native law firms are actually pitching and whether it holds up
What happens to junior associates as AI takes over entry-level legal work
Why every legal tech vendor sounds the same right now and how to cut through it as a buyer
Build versus buy: why building in-house almost always ends up abandoned
Mary's one piece of advice for legal professionals trying to catch up on tech
Connect & Visit:
Mary O'Carroll
LegalEng Consulting Group
Jessica Nguyen
Evolving with Jessica Nguyen -
Zijn er afleveringen die ontbreken?
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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.
Whether you're navigating your first in-house role or years into your career, this one will leave you thinking differently about how you show up.
Episode Threads
Early career stories that shaped how Eric thinks about preparation, improvisation, and holding your ground
What big law, the DOJ, and in-house each taught him about legal excellence and the value of relationships
Why legal excellence alone is not enough and what actually carries a career over the long run
Building teams where imperfect ideas are welcome and collaboration beats validation every time
The "day trader" trap and why your career trajectory matters more than any single hard day
How unconscious bias shows up in the legal profession and what junior lawyers can do about it
Why the billable hour is not going anywhere and what AI will actually change about law firm economics
What the future holds for junior lawyers, legal ops, and the people who use AI best
Eric's personal use of AI and why curiosity is the real superpower in the age of AI
Connect & Visit:
Eric Dodson Greenberg
Jessica Nguyen
Cox Media Group
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, powered by Sandstone. Learn more at sandstone.com.
