Evolving with Jessica Nguyen

Evolving with Jessica Nguyen

By Jessica NguyenBusinessTechnologyManagement
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Evolving with Jessica Nguyen episodes

  • Molly Finn on Embracing a Nonlinear Career

    Eighteen years at one company rarely means a straight line, and Molly Finn's career proves it. From a startup thrown into chaos to nearly two decades at eBay, her path was anything but linear, and she's using that same restless curiosity to make sense of what AI means for the next generation of lawyers.

    Jessica sits down with Molly Finn, Advisor at Sandstone, to talk about her nonlinear legal career, what she has learned building custom AI skills, and why she believes AI will reshape both the legal profession and the tools it relies on.

    Episode Threads

    • Molly Finn's winding career path from law school and an MBA to eighteen years at eBay

    • How her first startup job turned her into an employment law specialist in eighteen months

    • Embedding inside Cisco's HR team and treating legal and HR as one shared unit together

    • Why a linear path into law is disappearing as AI reshapes early-career legal work now

    • Building a custom Claude Skill for her resume and catching where the AI quietly drifts

    • Why general AI models still fall short compared to legal-specific, filtered AI tools

    • Trust, walled data, and the risk of leakage across different AI tools in one company

    • The coming rise of an agent officer role built to monitor and manage AI agent drift

    • Rethinking the legal tech stack to make tools genuinely easy to use, fun, and simple

      • Connect & Visit:

      • Molly Finn

      • Jessica Nguyen

      • Sandstone


        • 47 min
      • Virginia Johnson: Betting on Yourself

        She spent two decades climbing toward the titles, the raises, the next rung. Then she stepped off the ladder entirely, just to find out what she actually wanted.

        Jessica sits down with Virginia Johnson, Partner at Outside General Counsel (OGC), to talk about the relationships that built her career, the sabbatical that redefined it, and what she looks for now in a role, a founder, and herself.

        Episode Threads

        • Why she chose Weil Gotshal's securities litigation group for the mentors, not the law

        • The leap from litigator to Goldman-owned reinsurance business through a cold connection

        • Raising her hand for the messy assignments nobody else wanted to take on early on

        • How a mentee's tip about her CEO father led straight to the CLO role at Aspen Aerogels

        • What changes when you carry the added scrutiny and pressure of being a public company GC

        • Why she left her CLO role last summer for a sabbatical instead of chasing the next job

        • The two red flags that make her pass on a role no matter how good it looks on paper

        • Getting into VC investing through Mendoza Ventures and Bambelei Ventures as an advisor

        • What twenty years of mentoring taught her about giving without expecting anything back

          • Connect & Visit:

          • Virginia Johnson

          • Jessica Nguyen

          • Sandstone

            • 56 min
          • Alexandra Sepulveda: Curiosity is a Superpower

            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 mentorship, management lessons, outside counsel dynamics, and where AI fits into the future of legal work.

            Episode Threads

            • Why curiosity became her professional superpower

            • Losing everything moving from Chile to the US as a kid

            • Learning management the hard way, mistake by mistake

            • The many flavors of a well-timed "mm-hmm"

            • Why keeping receipts builds trust with the business

            • Earning respect for legal without becoming the ego police

            • The Princess Bride themed survey on outside counsel

            • Why $1,100 an hour does not mean faster AI-assisted work

            • Her pitch for a universal summer camp booking app

              • Connect & Visit:

              • Alexandra Sepulveda 

              • Trust & Will

              • Jessica Nguyen

              • Sandstone

                • 55 min
              • Dina 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

                    • 54 min
                  • Trista 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

                        • 1 hr 10 min
                      • Deborah 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

                            • 54 min
                          • Catherine 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

                                • 55 min
                              • Mary 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

                                    • 41 min
                                  • Eric 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

                                        • 1 hr 12 min
                                      • 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.

                                        3 min

                                      About Evolving with Jessica Nguyen

                                      From the publisher's feed

                                      The legal industry is changing fast, and the best legal and business leaders aren't waiting for permission to evolve.