Pioneers and Pathfinders

This week, we’re revisiting our conversation with Leah Molatseli, formerly of Contract Alchemists. Since her appearance on the podcast, Leah has taken on a new role as Country Liaison in South Africa for the legal tech company Saga, where she is still helping lawyers navigate technology, innovation, and more recently AI. In this wide-ranging episode, Leah shares her perspective on the South Africa...

Today's guest is Leslie Grandy, an author, speaker, and trusted advisor to CEOs, product leaders, and teams. Leslie's career has taken some fascinating turns—from working in the film industry to guiding major brands on strategy and innovation. She's also deeply committed to education, having taught product leaders through The Product Guild, the University of Michigan Center for Entrepreneurship, a...

This week, we're joined by David Freeman Engstrom and Natalie Knowlton from the Deborah Rhode Center on the Legal Profession at Stanford Law. David, who serves as co-director of the Center and holds the LSVF professorship in law, has devoted his work to access to justice issues in millions of often overlooked cases, such as debt collection, eviction, foreclosure, and child support. Earlier this ye...

This week, we're joined by Jason Marty, CEO of Lumio, a company helping legal leaders grow their businesses and adapt to the age of AI. Jason brings a wealth of experience to the new venture. He started in internet program management before moving into the legal industry, where he served as global COO at both Baker McKenzie and Bryan Cave Leighton Paisner. He later co-founded Lumio alongside Jae U...

We're pleased to welcome back Jordan Furlong. Jordan is one of the legal industry's leading voices on the future of the profession. He continues to advise legal organizations through his consulting practice, Law21, and is currently working on a new book exploring how generative AI will reshape the practice of law, which is set to be published next year. In this episode, we talk about the balance b...

Today's guest is Jonathan Petts, co-founder and CEO of Upsolve, a nonprofit helping low-income Americans overcome debt at scale. Jonathan's career has been focused on bankruptcy law, from clerking for bankruptcy judges to practicing at top New York firms. In 2016, he co-founded Upsolve, and since then, the platform has become the nation's most visited nonprofit financial education site. Its free b...

This week, we’re catching up with Ivy Grey, a legal tech entrepreneur, writer, and longtime friend of the podcast. We first spoke with Ivy three years ago about her fascinating background in anthropology and journalism, as well as her work at WordRake, where she's now chief strategy & growth officer. She also continues as an advisor to PerfectIt, a proofreading tool for legal professionals. In thi...

We’re excited to welcome back Lucy Bassli, founder and principal at InnoLaw Group. Lucy is a leading voice in legal operations and contract lifecycle management (CLM), helping organizations rethink how they handle contracts through smarter processes and technology, including—of course—AI. Lucy is an advisor to several legal tech companies. In our conversation, Lucy shares why so many people are fe...

With the school year just around the corner, we're going back to a great episode featuring Professor Nicole Morris of Emory Law. Nicole wears many hats. She's not only a professor, but also leads the TI:GER program, which brings together students from law, business, and engineering to turn ideas into real world innovations. Since we last spoke with her, she has become the Faculty Director of Emory...

As summer winds down, we're taking a moment to revisit one of our favorite conversations—this one with Denise Robinson, founding principal of The Still Center. Denise is a belonging & well-being consultant who helps lawyers and legal organizations cultivate personal resilience, build deeper connections, and create more inclusive workplaces. In this thoughtful and inspiring episode, Denise shares h...

Today's guest is Reena SenGupta, one of the true trailblazers in the legal world. She's executive director of RSGI, a global think tank focused on helping the legal industry build a more sustainable future. Reena’s path into law and innovation wasn't exactly traditional. She started out running her family's business through a recession, which led to some eye-opening interactions with lawyers and u...

We’re excited to welcome back Nicole Bradick, one of our earliest guests on the podcast. Since last we spoke, a lot has changed. Nicole is now global head of innovation at Factor, following the acquisition of her design and development studio, Theory and Principle. She's also an advisor at both Paladin and LEGA, continuing to help push the boundaries of legal tech and justice innovation. In this e...

Today, we’re joined by Ian Nelson, co-founder of Hotshot, a video-based learning platform that helps lawyers pick up essential legal, business, and technology skills in a more modern, practical way. Ian started out as a corporate lawyer who quickly found himself drawn to more innovative approaches to legal work. After being inspired by a firm in the UK, he jumped into something totally new—Practic...

We're excited to welcome back Maya Markovich, a familiar voice on the podcast and a leading thinker in legal innovation and AI strategy. Since her last appearance with us, Maya has taken on a new role as vice president of the American Arbitration Association Institute, the thought leadership and R&D arm of the AAA-ICDR. She is also still serving as executive director of the Justice Technology Asso...

Today's guest is Oded Oren, the founder and executive director of Scrutinize, a nonprofit that uses data analytics, AI, and legal research to shed light on complex judicial data. Before starting Scrutinize, Oded was a public defender in the Bronx. While there, he began digging into publicly available court data to spot patterns in how judges were ruling, an approach that soon evolved into the foun...

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 tec...

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...

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,...

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 lega...

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 La...

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. Ac...

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 forwa...

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 veter...

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 interdiscip...

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...