Podcast
Legal Leaders
Hosted by Ali Rafie · EN
Hear from industry leaders in the legal and business world.
11episodes
Episodes
Newest firstAll episodes
EP 38: Reflecting on 2L at Berkeley Law - Recruiting, Grading, AI & Law School Culture
4w ago00:52:00Tap to summarizeWe're officially 3L's!After finishing our 2L year at Berkeley Law, I sat down with classmates Riya Dhanjal, James Courser, and Rameses Neale to reflect on law school, Big Law recruiting, AI, burnout, networking, and student life.We discuss Berkeley Law’s culture and grading system, the realities of accelerated Big Law recruiting, the growing role of AI in legal practice, and what we wish we knew before starting law school.Topics include:• Big Law recruiting and networking advice• AI in legal education and practice• Berkeley Law culture and student life• Practice area selection and firm differences• Journals, externships, and extracurriculars• Burnout, balance, and imposter syndrome
Transcribe →EP 37: How to Build a Successful Career in Law: Insights from Dina Segal, CLO of Gusto
May 800:35:34Tap to summarizeDina 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.
Transcribe →EP 36: From Employment Lawyer to CLO of Eventbrite - Leading Through IPO, Pandemic, and $500M Exit
Apr 300:31:15Tap to summarizeLisa Gorman is one of the most accomplished legal executives in tech. She spent nearly nine years at Eventbrite, rising from employment counsel to General Counsel and Chief Legal Officer. During her tenure, she helped lead Eventbrite's legal strategy through its IPO, global expansion, the pandemic's devastation of the live events industry, and ultimately a $500 million acquisition by Bending Spoons.In this episode, we discuss her unconventional path from English literature major to tech CLO, how she transitioned from law firm partner to in-house counsel by organically becoming part of her client's team, and what it takes to expand beyond your core expertise. Lisa shares how she went from employment law to leading litigation, content moderation, product, privacy, regulatory, and the entire legal function. We explore the value of building trust and tenure at a single company, the role of legal AI tools like GCAI in modern practice, and her experience leading Eventbrite's content moderation program and DSA compliance. Lisa also addresses what the future holds for junior lawyers in an AI-driven world and reflects on her biggest career highlight of leading the $500M sale to Bending Spoons.Lisa offers candid advice for law students and early-career lawyers about finding work that doesn't feel like a grind, the value of staying when you find the right fit, and keeping an open mind about where your legal career might take you.#Eventbrite #ContentModeration #TrustAndSafety #DSACompliance #LegalTechnology #GCAI #LegalOperations #MergersAndAcquisitions #BerkeleyLaw #LawSchool
Transcribe →EP 35: Leading Legal Teams & Managing Yourself as GC with Executive Coach Dennis Adsit
Feb 1700:42:20Tap to summarizeIn this episode, I sit down with Dennis Adsit, an executive coach with over a decade of experience helping leaders navigate transitions and build high-performing teams. Dennis holds a PhD in industrial psychology and has coached everyone from startup founders at Techstars to C-suite executives, with prior experience leading Six Sigma implementation and global call centers at Intuit.Dennis reveals why most lawyers' resumes fail: they focus on credentials and responsibilities instead of business impact. He introduces his WAS-DID-IS framework, which structures your story around the situation you faced, the actions you took, and the measurable results you delivered. We explore his four-pillar model of executive effectiveness: setting strategic context, executing efficiently, building talent, and managing yourself. Dennis explains how AI is changing leadership priorities, making the "generosity gene"—your ability to celebrate your team and create connection—more critical than ever for retaining talent and maintaining productivity.For lawyers transitioning from firms to in-house roles or moving into general counsel positions, Dennis breaks down the specific mindset shift required: from individual contributor solving legal problems to leader building platforms for others to succeed. He also offers tactical advice for early-career professionals on saying yes to diverse opportunities and becoming known as reliable problem-solvers.About Adsum Insights: www.adsuminsights.comhttps://medium.com/@dennis_adsit/lawyers-and-the-mystery-of-the-missing-case-efffd3106814
Transcribe →EP 34: Dan Haley, CLO of Flock Safety: Building & Leading Legal Teams at High-Growth Companies
Feb 400:55:03Tap to summarizeI spoke with Dan Haley, Chief Legal Officer of Flock Safety, to walk through a career that spans nearly a decade in Big Law and senior legal leadership roles at some of the fastest-growing technology companies in the country. Dan shares what it’s really like to make the transition from law firms to in-house, including the tradeoffs, surprises, and lessons he learned along the way.We talk about navigating high-stakes moments such as major acquisitions, IPOs, and scaling legal teams through periods of rapid growth and uncertainty. Dan also discusses his current role at Flock Safety, the legal and constitutional questions surrounding public safety technology, and how he thinks about privacy, the Fourth Amendment, and responsible innovation from the CLO seat.Throughout the conversation, Dan reflects on career decision-making, leadership, and why focusing on doing excellent work, staying open to unexpected opportunities, and building genuine professional relationships can matter more than rigid long-term planning. This episode is relevant for law students, associates, and in-house lawyers interested in high-growth tech, legal leadership, and building a meaningful career over time.
Transcribe →EP 33: Building the Future of Legal AI with Justin McCallon, Founder of StrongSuit
Jan 1900:38:47Tap to summarizeJustin McCallon is the Founder and CEO of StrongSuit, an AI platform built to modernize and accelerate core legal workflows.Justin started his career as a practicing attorney before leading large-scale analytics, transformation, and AI initiatives at AT&T and DIRECTV. In our conversation, we cover his path from law to consulting to building a legal AI company, what he’s seeing in the legal tech market right now, and how legal teams are actually adopting AI in practice.We also dig into StrongSuit’s product: AI-driven legal research, drafting, and document review, plus how StrongSuit compares to legacy research platforms and where Justin believes the biggest ROI is for litigators. Justin also shares a bold prediction: by the end of 2026, it may be possible to automate 50–99% of common litigation tasks with AI agents—and what that means for lawyers building careers in a rapidly changing profession.Www.Strongsuit.com#LegalTech #AI #Litigation #LegalAI #LawSchool #InHouse #LawFirm #LegalInnovation #Startup #JD
Transcribe →EP 32: Autonomous Vehicle Regulation: A Conversation with Ian Poirier (Toyota Research Institute)
Jan 1200:41:32Tap to summarizeIan Poirier is the Associate General Counsel at Toyota Research Institute (TRI), where he works at the intersection of autonomous vehicles, robotics, safety, and policy. We talk about how autonomous vehicle regulation has evolved over the past decade, including Ian’s experience moving from Lyft’s early AV efforts to Toyota’s long-term research and safety programs. Along the way, he explains why one of the hardest questions in autonomy remains defining what “safe enough” actually means when formal standards lag behind the technology.We also walk through Ian’s in-house career path—from UCSF Law to Wikimedia, Lyft, and ultimately Toyota—and the unconventional choices that shaped it. Ian reflects on why mastering legal fundamentals, taking on responsibility early, and being willing to operate without formal training or process became the foundation for his career in emerging technology.
Transcribe →EP 31: Coupa CLO Julia Taylor: From BigLaw to Eventbrite's $1.8B IPO
Jan 100:59:53Tap to summarizeJulia Taylor is the Chief Legal Officer at Coupa and a Berkeley Law alum. We unpacked her path from Big Law to becoming the first lawyer at Eventbrite, where she spent nearly twelve years and helped guide the company through its $1.8B IPO. Julia reflects on her early influences, including her time working on Capitol Hill for Senator Dianne Feinstein and Jerry Brown, and how those experiences shaped her pragmatic, solutions-oriented approach to leadership. We also talked about what it actually means to succeed in-house. Julia explains why deeply understanding the business, building trust across teams, and staying calm under pressure are the traits that matter most, especially during high-stakes moments. The conversation also covers some of the most challenging moments of Julia’s career, including leading through COVID-era layoffs, navigating risk when Eventbrite unexpectedly became a platform for vaccine registration, and knowing when it was time to step aside to let the next generation of leaders rise. Julia offers candid advice for law students, associates, and in-house lawyers on career strategy, risk tolerance, and why being “ruthlessly practical” is often the key to long-term success.#LawSchool #LegalLeadership #LegalTech #Coupa #Eventbrite #IPO #BigLaw
Transcribe →EP 30: Reflecting on 15 Years at Microsoft with Jason Barnwell
Dec 300:52:48Tap to summarizeJason Barnwell just joined Agiloft as Chief Legal Officer after 15 years at Microsoft, where he most recently served as GM and Associate General Counsel for Monetization and Business Planning. I spoke with Jason about his career path from MIT engineering grad to software engineer to leadership at one of the world's leading tech companies. We discussed his work driving digital transformation within Microsoft's legal department and his philosophy on developing legal talent, including his concept of getting to "minimum viable lawyer" as quickly as possible. Jason also shared insights on how technical backgrounds enhance legal practice and his perspective on AI in the profession. His view: the technology isn't the challenge, it's getting legal organizations to adapt their structures and incentives.#LegalTech #Microsoft #Agiloft #InHouseCounsel #LegalLeadership #DigitalTransformation #BerkeleyLaw #LawSchool #CLM
Transcribe →EP 29: Building a Legal Tech Brand with Colin Levy & Innovating the Future of Law
Aug 800:39:30Tap to summarizeI spoke with Colin Levy, General Counsel at Malbec, an innovative CLM company. Colin shares his in-house journey, his passion for legal technology, and how he's helping bridge the gap between law and tech. Colin discusses the importance of building a personal brand, embracing AI in the legal industry, and the future of law schools adapting to tech innovations. He also offers insightful advice for new lawyers looking to break into the legal tech world.Tune in for a conversation filled with career insights, tech trends, and actionable advice for lawyers and legal professionals!Links:Colin Levy's Website: https://www.colinslevy.comMalbec.io - Legal Tech Solutions: https://www.malbek.io/
Transcribe →