This week, we're revisiting one of our most compelling conversations—with Damien Riehl, a technology lawyer, coder, and thought leader at the intersection of law and innovation. At the time of our conversation, Damien was vice president and Solutions Champion at vLex. vLex recently made headlines with its acquisition by Clio, which is a move that signals a new chapter in the evolution of legal technology. So, we thought now is an apt time to replay this conversation with Damien.

His career has spanned roles at Thomson, Reuters, Fastcase, and the SALI Alliance. Our discussion touched on a wide range of topics: his early experience as a tech attorney, the complexities of confidentiality and legal AI, music copyright, and the enduring value of a liberal arts education. We hope you enjoy this encore episode as much as we did.

Our guest today is Damien Riehl, vice president and Solutions Champion at vLex, a platform using artificial intelligence solutions to streamline workflows and provide lawyers with greater access to knowledge and resources. Damien was a tech attorney for more than 10 years when he made the leap to Thomson Reuters as Senior Product Strategist, where he developed innovative legal technology involving artificial intelligence, machine learning, and natural language processing. Inspired by Ed Walters’ efforts to democratize the law, Damien later joined Fastcase, where he served various roles building out legal tools and systems. In his current position at vLex, Damien helps lead the design, development, and expansion of products. Additionally, Damien is part of the leadership team at the Standards Advancement for the Legal Industry (SALI) Alliance. He is also co-founder of All the Music LLC, a project that involved copyrighting 471 billion melodies and placing them in the public domain. In 2019, Damien delivered a TED Talk in which he describes this process and offers a new way to handle copyright infringement lawsuits in music.

In today’s conversation, Damien discusses vLex's newest product—Vincent AI, his decision to leave practice and join Thomson Reuters, the genesis of All the Music, and the future of teaching legal research.

Read the full transcript of the episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_Bestof_DamienRiehl.pdf

This week, we host Dennis Garcia, someone has been a leader at the intersection of law, technology, and business for over 25 years. He is currently Assistant General Counsel at Microsoft, where he leads the legal support function for the Microsoft Americas Strategic Customer Pursuit, Partner Solutions, and Sales Enablement & Operations teams—among many other responsibilities. Dennis’ journey into tech law began during law school, where he had the opportunity to support in-house counsel at IBM. That early exposure sparked a lasting interest in the intersection of legal practice and innovation. After graduating, he was hired by IBM for a full-time position, negotiating licensing and sale agreements. Dennis then served as counsel at Accenture, advising the Communications & High Tech and Financial Services Market Units.

Today, Dennis shares stories from his early days at IBM, and how he developed his skills as a deal lawyer at Accenture. He also discusses the different ways he has been using Copilot in his work, as well as the ethical considerations of using generative AI in legal practice.

Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_DennisGarcia.pdf

Today, we're joined by Kevin Walker, founder and CEO of Centari, a deal intelligence platform that combines secure LLMs with trusted legal precedent to accelerate transactions. Kevin started as an M&A attorney at Paul Hastings before moving in-house to lead teams in real estate and private equity. Drawing on his experience representing businesses, he took the entrepreneurial leap to found Centari, where he has built products that he and his peers always wished they had as dealmakers.

In our discussion, Kevin speaks with us about his passion for dealmaking and why he decided to transition to business. We also talk about how he and his team at Centari are making use of deal intelligence. Additionally, Kevin offers thoughtful advice for lawyers contemplating a career pivot into business or tech.

Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_KevinWalker.pdf

This week's guest, Dr. Roland Vogl, is a leading voice in legal education and the legal profession. He is the Executive Director of the Stanford Program in Law, Science, and Technology, and a lecturer in law at Stanford Law School. Dr. Vogl also co-founded and leads CodeX, the Stanford Center for Legal Informatics, where he drives cutting-edge research for the application of technology in the legal profession. In addition to his work at Stanford, Dr. Vogl serves as a visiting professor at the University of Vienna, where he teaches US intellectual property law. He is also a co-founder and board member of Merico, Inc., a platform focused on software engineering metrics. Dr. Vogl plays an active role in the legal tech ecosystem, advising legal tech and legal generative AI companies. Since 2022, he has served on the executive committee of the International Association for AI and Law.

In this episode, Dr. Vogl discusses his journey from legal practice to academia, offering insights into the unique culture at Stanford Law School that helped spark the creation of CodeX. We also explore how CodeX selects its projects and how it’s adapting to the transformative rise of generative AI.

Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_Dr.RolandVogl.pdf

This week, we're speaking with Anastasia Boyko, a legal futurist and product evangelist at Filevine, a legal work platform for law firms and businesses. Anastasia has had a diverse career path, from practicing tax law to transformational and change management roles to legal education. She has created and led innovative programs at Yale Law School and the University of Utah SJ Quinney College of Law, where she has applied her knowledge of legal practice and business. Today, at Filevine, she collaborates with her team on creating and incubating new products in legal tech.

In our conversation, Anastasia tells us about her journey to the legal field and why she ultimately decided to finish law school. We also discuss the need for empathy and kindness when training new lawyers, her exciting role as a legal futurist, and why law students should develop a range of skills.

Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_%20AnastasiaBoyko.pdf

We're joined today by a true leader and team-builder in legal tech: Mark Smolik, Chief Legal Officer at DHL Supply Chain Americas. Mark has been at the forefront of innovation in the industry for decades, having previously served as Senior Corporate Counsel at the Sherwin-Williams Company, as well as General Counsel & Secretary, Head of Human Resources, and Ethics Officer at Safelite AutoGlass. Across these various roles, Mark has been relied on for executing legal, compliance, and business strategies that mitigate risk and drive value.

In our discussion, Mark talks about the DHL Legal Innovation Summit in June, his approach to team-building and shaping culture, the important advice he received on delivering value, and his DHL team's approach to managing risk.

Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_MarkSmolik.pdf

We're back with part two of our conversation with Justin Ergler and Keith Maziarek, two sharp voices at the forefront of legal innovation and co-hosts of the Off the Clock podcast. In this second episode, we dig deeper into the forces driving legal transformation. We talk about what motivates real change in the industry, why managing change—not just demanding it—is key to moving the industry forward, and why culture is such a critical but often overlooked component of successful change management.

Whether you're inside a law firm or on the client side, this is a candid, practical look at the challenges and opportunities of modern legal practice. Thanks for taking the time to listen in. 

Read the full transcript of this episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_KeithMaziarek_JustinErlger_Pt.2.pdf

This week, on Pioneers and Pathfinders, we're doing something a little different, with a special two-part conversation featuring Justin Ergler and Keith Maziarek, co-hosts of the Off the Clock podcast and board members of the Legal Value Network. Now, you may remember Keith from a previous episode. He's the Director of Pricing and Legal Project Management at Katten Muchin Rosenman. Justin, a veteran of GlaxoSmithKline, now leads his own consulting practice focused on alternative fee arrangements and innovative legal service delivery.

In part one of our wide-ranging discussion, we talked about why this is a great time to enter the legal profession, the ongoing frustrations with the pace of change, and how law firms and legal departments are rethinking billing structures. 

Read the full transcript of this episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_KeithMaziarek_JustinErlger_Pt.1.pdf

Today, we revisit one of our most thought-provoking conversations, this time with Dr. Megan Ma. Since she joined us on the podcast, Dr. Ma has co-founded and become the Executive Director of the Stanford Legal Innovation through Frontier Technology Lab—otherwise known as liftlab. With a rich background in political science, economics, health law, and economic law, Dr. Ma brings a truly interdisciplinary lens to the future of legal education and technology. In our conversation, she shares her insights on how we train the next generation of lawyers, why mentorship and thoughtful design matter, and what it means to build a future-ready legal profession. Whether you're a seasoned practitioner or just starting your career, this episode is full of wisdom and perspective on where the law is headed and how we will get there.

Our guest this week is a leading thinker on the application of generative AI in the legal profession. Dr. Megan Ma is the associate director of Stanford’s Law, Science, and Technology Program, as well as the Stanford Center for Legal Informatics—better known as CodeX. She also teaches courses in computational law and insurance tech. Dr. Ma has a background in a variety of fields: She majored in political science and economics, has master's degrees in health law and economic law, and earned her PhD in law. Additionally, Dr. Ma is an advisor to the PearX for AI program, and serves as editor-in-chief for the Cambridge Forum on AI, Law, and Governance, as the managing editor of the MIT Computational Law Report, and as a research affiliate at Singapore Management University in their Centre for Computational Law.

We had a fascinating conversation about Dr. Ma’s lifelong interest in linguistics, how "empathetic" large language models can be for users, how generative AI could change lawyer mentorship, and her thoughts on the future of technology in the profession.

Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_Bestof_Dr.MeganMa.pdf

Today, on Pioneers and Pathfinders, we're joined by Farrah Pepper, Chief Legal Innovation Counsel at Marsh McLennan—and a true force in the world of legal innovation. Farrah has built a career at the intersection of law, technology, and strategy, from founding Gibson Dunn's Global eDiscovery practice to leading GE's Discovery Center of Excellence to shaping the future of legal innovation at Marsh McLennan. She also plays a key role at Legal Data Intelligence, helping professionals unlock the power of legal data to solve real-world challenges.

In our conversation, Farrah shares what drives her boundless energy, how to build community in the legal tech space, and why the design phase is critical to innovation. We also talked about the importance of leadership support and the lessons she's learned along the way. Farrah was thoughtful and inspiring, so don't miss an episode with one of the leading voices in legal transformation.

Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_FarrahPepper.pdf