Legal Leaders

I 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.

Justin 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

Ian 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.

Julia 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

Jason 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

I 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/

David Cunningham is the Chief Innovation Officer at Reed Smith LLP, where he leads legal tech transformation for 2,000+ lawyers across 34 offices. But his focus goes far beyond technology—he’s rethinking the culture and workflows that shape how legal work gets done.With a background in legal operations and data analytics, David has become one of the leading voices in the push for practical, scalable innovation in Big Law. He’s also the founder of Legal Metrics, a nonprofit initiative improving how firms and clients measure performance.In this episode, David pulls back the curtain on what firms are really doing with AI and how change actually happens at scale. We talk about the biggest barriers to adoption (hint: it’s not the tools), how some seasoned partners are leapfrogging junior lawyers in AI use, and what law firms can learn from tech companies.We also explore:-How David’s background in client-facing innovation shapes his work inside the firm-What “working backwards from the client” looks like in Big Law-Why the hardest part of innovation is behavior—not technology-The metrics that actually matter for modern legal teams-How law students and associates can position themselves as innovation leaders-If you’re curious about the future of legal work and what’s happening behind the scenes at some of the world’s top firms, this episode is for you.🎧 Subscribe if you enjoyed the episode! #LegalTech #Innovation #BigLaw #AI #LegalLeadership #FutureOfLaw #LegalOps #LawFirmStrategy

Aboud Chaballout was on track to become a doctor. He studied human biology at Cornell, completed a Fulbright, and even worked in healthcare consulting in Qatar. But somewhere along the way, he realized his interests pulled more toward entrepreneurship than medicine.He went to law school, launched a startup after 1L, and never looked back. Since then, he’s built and sold multiple healthcare businesses, worked at a law firm, and eventually founded his own boutique practice focused on advising startup founders at the intersection of law, healthcare, and AI.In this episode, we talk about pivoting careers, embracing nontraditional paths, and how he’s using everything he’s learned—legal, technical, and entrepreneurial—to help clients build.We talk about:▪️ Lessons from launching multiple companies▪️ How consulting in Qatar shaped his global perspective▪️ Using AI to enhance transactional lawyering▪️ What solo founders need that Big Law doesn’t offer▪️ Whether a JD is still worth it in the age of automationAboud’s career is a case study in reinvention. Listen in if you're curious how law, tech, and healthcare intersect—or what it really looks like to build a practice from scratch.

I sat down with three of my classmates—Alex Kang, Laith Hourani, and Aman Madan—to unpack the highs, lows, and everything in between from our 1L year at Berkeley Law.We talked about:What brought us to law schoolHow we navigated the pressure of grades and early recruitingThe good, bad, and weird of law school social lifeAdvice we wish we had on day oneAnd yes, we even got into the not-so-glamorous parts of networking and why some of us struggled with it. This one’s for incoming law students, current 1Ls, or anyone curious what it’s actually like behind the Reddit posts and glossy brochures.

Joseph Schohl is a five-time General Counsel and former Fortune 500 CLO who became a public company GC by the age of 35. Over the course of his career, he’s held leadership roles at Baxter Healthcare, DaVita Kidney Care, and Radiology Partners, while also building a reputation for empowering the next generation of in-house counsel.Joe is the founder of his own firm, General Counsel West, which provides strategic legal support to healthcare companies. He also created the Inside Counsel Academy—a program designed to help in-house lawyers think like business leaders and grow into effective legal executives. In addition, he hosts the podcast "Becoming the GC," where he interviews legal leaders on what it takes to thrive in-house.In this episode, Joe shares his insights on transitioning from Big Law to the GC seat, the value of pairing legal and business education, and how coaching and content creation have become a meaningful part of his journey. We hope you enjoy the episode!🎧 Learn more at: generalcounselwest.com📺 Check out Joe’s podcast: Becoming the GC#LegalLeadersPodcast #GeneralCounsel #InHouseCounsel #LegalLeadership #InsideCounsel #HealthcareLaw #CareerDevelopment #JDValue #MBALawyer #LegalCareer

Roger Royse is a partner at Haynes Boone and the founder of the Royse Law Firm. Over his career, he’s advised thousands of startups, built a name in tax and startup law, and authored two books sharing hard-earned lessons with founders and lawyers alike.Roger’s story goes well beyond law. He’s a CPA, an entrepreneur, an athlete, an author, and a pancreatic cancer survivor. His perspective is shaped by both deep professional wins and personal battles.In this episode, Roger reflects on his early years building a business tax–centered law firm from scratch, what it means to truly “own your practice,” and why trying different types of law early matters. Check out Rogers content on his Youtube at @royselaw or his podcast 10000 Startups; Legal strategies for startup success. We hope you enjoy the episode.

Jon Gavenman is a seasoned corporate attorney and partner at Cooley, where he’s been advising startups and public companies since 2008. With a career spanning more than three decades, Jon has had a front-row seat to Silicon Valley’s evolution—helping companies scale, navigate acquisitions, and raise capital.Starting as a math major at Pomona College before earning his JD from UC Hastings/UCSF Law, Jon entered the legal field right as the tech industry was taking off. He built his expertise at Wilson Sonsini before joining Venture Law Group, a firm that pioneered taking equity in exchange for legal services, and later transitioned to Heller Ehrman before landing at Cooley.Jon has worked on major deals, including Halcyon's $100M Series C, Logic.io's $25M Series B, and G2’s $157M Series D, helping companies from early-stage financing through IPOs and acquisitions.In this episode, we discuss Jon's career, the business development side of law, and what makes a great long-term legal partner. Jon also shares his perspective on how partners approach client relationships and the key considerations for early-stage companies looking to scale. We hope you enjoy the episode.

Mark Pike is the Associate General Counsel at Anthropic, an AI research and safety company experiencing explosive growth. At the time of this podcast, the company raised a $3.5 billion Series E round, bringing its valuation to $61.5 billion, solidifying its position as a leader in AI development.Mark has a proven track record of making strategic career moves at companies on the verge of massive hyper-growth. He previously worked at Facebook and Slack, joining the latter when it was still a few hundred employees and participating in the $27.7 billion acquisition by Salesforce in 2021. Throughout his career, he has worked across platform policy, intellectual property, and privacy, helping shape legal strategy at some of the most innovative tech companies. In this episode, we dive into what it means to be an effective product counsel, how legal teams can work closely with product and engineering to launch new features, and the importance of prioritizing learning and growth in one’s career.We hope you enjoy the episode!

Ex Judicata is an employment platform and job board designed to connect attorneys with nonlegal career opportunities that make the most of their JD.https://exjudicata.com/⁠In this episode, I sit down with Kim Fine and Neil Handwerker, the co-founders of Ex Judicata. With extensive backgrounds in business development, recruiting, and the legal industry, they recognized a gap in the market and built a platform to help attorneys explore new career paths.Both Fordham graduates—Kim with an MBA and Neil with a JD—this is their second successful venture together, having sold their first company in the early 2000s. Since launching Ex Judicata, they’ve had over 100,000 unique visitors and have helped countless attorneys transition into new roles.This episode also marks the first sponsored episode of the Legal Leaders Podcast. Thank to Ex Judicata for sponsoring.

Aaron Brogan is the founder of Brogan Law, a boutique law firm specializing in cryptocurrency, fintech, and emerging technology. After graduating from Harvard Law, Aaron spent six years in Big Law in New York, first as a litigator before pivoting to crypto and fintech law at McDermott.In this episode, Aaron shares his inspiring journey—from navigating Big Law to launching his own firm in New York. He discusses the legal challenges of the crypto industry, his experience representing major players in blockchain and finance, and what it takes to build a successful law practice in an evolving regulatory landscape.You can reach Aaron at aaron@broganlaw.xyz.

In this episode, we’re joined by Kevin Liu, a partner at Goodwin Procter and a member of the firm's Strategic Technology Transactions and Licensing and Data, Privacy & Cybersecurity practices. Kevin shares his impressive career journey, which blends engineering and law, offering a unique perspective on the intersection of technology, privacy, and intellectual property. Kevin’s expertise spans industries like cloud computing, mobile gaming, blockchain, AR/VR, and more. Before returning to Goodwin in 2020, Kevin spent time in-house as Head of Product and Privacy at a late-stage B2B software company. In this conversation, Kevin discusses his path from his engineering roots to becoming a partner at one of Silicon Valley's top firms, advising clients on complex legal matters in tech and privacy. Tune in to hear insights on how Kevin navigated his career, the evolution of technology law, and what it’s like working at the cutting edge of industries like cloud computing, gaming, and beyond.

Lindsey Mignano is the founding partner of SSM Law, a WBENC corporate law firm redefining the delivery of BigLaw services at affordable rates. SSM Law specializes in representing emerging technology companies, venture capital funds, and industry-adjacent service providers in critical areas like venture financing, M&A, tax law, and commercial contracts. As a fully virtual, women-led firm, SSM combines accessibility with a high-touch, personalized service model. In this episode, Lindsey dives into the challenges and successes of building a modern law firm focused on inclusivity and innovation. She shares insights into their flexible service models, like subscription-based legal support, their commitment to empowering underrepresented voices in law and business, and how SSM Law’s team delivers tailored legal strategies for startups and industry leaders alike. We hope you enjoy the episode!

Simi Raina is the Head of Legal at Webflow—one of the fastest-growing companies on the Forbes Cloud 100 list. Simi’s impressive career has taken her through some of Silicon Valley’s top tech companies, during major phases of hyper growth including Salesforce, Uber, and Visa. In this episode, Simi shares invaluable insights on networking, job hunting, and the unique aspects of in-house legal work, from product counseling to commercial transactions and negotiating budgets for the team. Her journey is inspirational we hope you enjoy the episode!

Dr. Ali R. Alemozafar is a partner at Wilson Sonsini. He focuses on IP counseling and works with companies at various stages of growth, from pre-financing startups to public companies. Prior to practicing law, Ali was an accomplished academic, acquiring his bachelor's in chemical engineering from Cornell and earning a Ph.D. in chemical engineering from Stanford. Ali was exposed to the field of patent law while at Stanford; he went on to earn his JD from UCSF Law. This interview covers Ali's career timeline and speaks to his passion for the STEM field and the companies he helps daily.

Bradley Krack is a partner at Gunderson Dettmer in Silicon Valley. A former engineer and submarine officer, Brad specializes in guiding high-growth tech companies through complex deals. He recently celebrated his thirteenth year with Gunderson, where he represents companies in their financings, IPOs, and M&A transactions. His experience spans a variety of technology firms, including consumer internet, software, internet security, financial, and entertainment technology companies, as well as venture capital firms. Brad holds a bachelor's and a master's degree in materials science from Northwestern, as well as a J.D. from Berkeley Law. I hope you enjoy this episode as we discuss the value of hard work, discipline, and managing client relationships.