Evolving with Jessica Nguyen

By 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 ... more

Download on the App Store

Download on the App Store

Get it on Google Play

FAQs about Evolving with Jessica Nguyen:

How many episodes does Evolving with Jessica Nguyen have?

The podcast currently has 7 episodes available.

Evolving with Jessica Nguyen episodes:

September 16, 2026Dina Segal: Build, Iterate, Transform
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, and running legal teams through a period of rapid change.
Episode Threads
How years of litigation, tax, and FCPA work at a law firm built her career foundation

Her Miles Morales inspired philosophy on jumping in before you ever feel fully ready

How she was promoted to CLO from within Gusto instead of leaving for the new title

Her honest advice for attorneys who keep getting passed over for their first GC title

Why owning outcomes, not just helping or contributing, is what recruiters want to see

How Gusto hires for AI fluency and gives candidates hands on problem solving exercises

Running two legal AI hackathons and turning those ideas into real deployed tools

Using AI to monitor thousands of regulatory changes across federal and state law

Her work supporting women in legal through Sun Law and what she would build next
Connect & Visit:
Dina Segal

Gusto

Jessica Nguyen

Sandstone
...more
54min
September 02, 2026Trista Engel and Jessica Markowitz: Think Like an Executive
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, and what that outsider vantage point taught them about what GCs actually need to succeed.
Episode Threads
Buying and scaling Paragon without a legal background

Reaching Paragon Legal's 20th anniversary this year

Learning the business before making any changes

Growing the corporate team from four to nearly thirty

Pre-partnership planning, sharing performance reviews, and trust

Why "it's a business decision" frustrates the C-suite

Jessica Markowitz's Seven Deadly Sins of Legal

Hiring signals: coachability, grit, and internal locus of control

Closing hot takes on AI, budget shifts, and what CEOs want from GCs
Connect & Visit:
Trista Engel

Jessica Markowitz

Paragon Legal

Jessica Nguyen

Sandstone
...more
1h 10min
August 19, 2026Deborah Solmor on Preparing the Next Generation of GCs
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 Founder of Ready Set GC. They cover Deborah's path from Skadden to in-house leadership, the lessons that shaped Ready Set GC, and how she continues to build community for women in law.
Episode Threads
Leaving Skadden after two decades to go in-house

Realizing being a lawyer was the least important part of the GC job

The board meeting mistake that taught her "it's not about you"

Advice for senior attorneys trying to break into in-house roles

The Crock-Pot versus microwave analogy for working styles

Why outside counsel relationships matter beyond billable work

Building Ready Set GC and the Ascend program from scratch

What she'd do with her time if AI took over her job
Connect & Visit:
Deborah Solmor

Wisconsin Alumni Research Foundation

Ready Set GC

Jessica Nguyen

Sandstone
...more
54min
July 08, 2026Catherine Romero: Always Bet on Curiosity
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
...more
55min
July 08, 2026Mary O'Carroll on Bridging Law and Technology
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
...more
41min
July 08, 2026Eric Dodson Greenberg on Relationships and the Future of Law
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
...more
1h 12min
June 16, 2026 Evolving with Jessica Nguyen Trailer
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.
...more
3min

FAQs about Evolving with Jessica Nguyen:

How many episodes does Evolving with Jessica Nguyen have?

The podcast currently has 7 episodes available.