This week on Pioneers and Pathfinders, we’re joined by Wendy Jephson, CEO and co-founder of Let’s Think. The company operates in a space they call “behavioral science AI,” which is intended to transform workplace productivity in the legal profession. Wendy brings a rare dual qualification as both a commercial lawyer and a business psychologist, with deep expertise across health care and financial services. Previously, she served as head of Research & Ideation for Market Technology at Nasdaq, where she introduced scientific research methodologies to enhance innovation and development processes. A recognized thought leader, Wendy speaks globally on topics such as AI, surveillance, cognitive engineering, organizational resilience, and the intersection of conduct and culture with technology design. In our conversation, Wendy shares insights into the behavioral science behind legal professionals, the founding story and mission of Let’s Think, and her vision for the future of lawyer training and workplace transformation. Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_WendyJephson.pdf

Today, we’re joined by Jack Cushman, director of the Harvard Library Innovation Lab, where he and his team are reimagining how library principles can shape the future of legal technology. Jack is a software engineer and appellate attorney who previously led the development of the Caselaw Access Project. He has also taught computer programming at Harvard Law School, served as a Berkman fellow, and sat on the board of the ACLU of Massachusetts. At the Library Innovation Lab, Jack explores how libraries can better collect, preserve, and share knowledge. His current work focuses on the fragility of digital cultural memory and the emergence of AI as a new form of knowledge. In our conversation, Jack reflects on his journey from computer programming to law school, the evolving mission of libraries in the digital age, and the skills lawyers need to thrive in an AI-driven world. He also shares his perspective on how we should measure the impact and reliability of AI systems in legal practice. Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_%20JackCushman.pdf

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 African legal community, her passion for writing, and the importance of purpose-driven work. It’s a conversation full of inspiration and forward-thinking ideas. Thank you for listening. We will return next week with a new episode. This week, we welcome Leah Molatseli, founder of Contract Alchemists, a company with the goal of modernizing legal teams through legal operations, agile methodologies, and technology. Leah has over 10 years of experience in the legal field, and has a certificate in Entrepreneurship and Innovation from the University of Notre Dame. After practicing for a few years, she co-founded Lenoma Legal, a virtual legal tech startup aimed at helping small businesses in South Africa. Prior to starting Contract Alchemists, Leah was head of business development at Legal Interact, a legal tech company. She is also a speaker, a published author, and a council member at the University of the Free State. Additionally, she recently joined LexisNexis South Africa as an author and became a Voice and Brand Council Member at the Corporate Legal Operations Consortium (CLOC). In today's conversation, Leah discusses the legal community in South Africa, how she approaches her writing, the TV shows that inspired her to become an attorney, and how being purpose-driven shapes her decision-making. Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_LeahMolatseli.pdf

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, and as guest lecturer at the University of Washington's Foster School of Business. Leslie recently added author to her list of accomplishments with the release of her book, Creative Velocity, which explores how to drive better results and better collaboration through creativity and the thoughtful use of generative AI. In our conversation, Leslie talks about the importance of embracing a creative career path and discovering her personal superpower. We talk about her thesis that creativity is a learnable, repeatable system. We also discuss why reframing problems is often the key to solving them, the role of culture and creative problem solving, and her thoughts on how organizations should be approaching AI tools. Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_LeslieGrandy.pdf

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 year, he published Rethinking the Lawyers’ Monopoly, a major contribution to the ongoing debate about the future of legal services and regulation. You may remember Natalie from her appearance on the podcast in 2023. Since then, she stepped into the role of associate director for legal innovation at the Rhode Center, where she focuses on legal technology, court modernization, and regulatory reform. Just this summer, the Center released a groundbreaking report, which she and David co-wrote, called Legal Innovation After Reform: Five Years of Data on Regulatory Change, which analyzes the reforms in Arizona and Utah. In today's episode, David and Natalie share insights from that report and discuss the broader implications for the legal system. We will also hear from David about his unexpected journey from coaching high school football in the Mississippi Delta to joining the Stanford Law faculty. Additionally, we talk about what today's law students need to understand about how technology is reshaping the practice of law. Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_DavidEngstrom_NatalieKnowlton.pdf

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 Um and Ed Sohn, both past podcast guests, with a vision of creating a “service as software” company for the business of law. Jason shares Lumio’s origin story, his career journey, and what excites him most about the evolving legal tech landscape. If you want to know what “service as software” means to Jason, take a listen now. Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_JasonMarty.pdf

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 between the commercial and societal responsibilities of today's lawyers, the evolving purpose of the profession in the age of AI, and his recommendations for firms navigating this wave of change. Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_JordanFurlongReturns.pdf

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 bankruptcy tool has already helped more than 14,000 families relieve over $600 million in debt. Jonathan talks about his path into bankruptcy law, the story of founding Upsolve, the importance of building strong nonprofit partnerships, and the advice he’d give his younger self. Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_JonathanPetts.pdf

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 this episode, Ivy walks us through her “sandwich” approach to writing with generative AI, and how new tools in WordRake are helping users write more clearly and confidently. We also talk about staying ethically grounded while using gen AI, and how emerging tech might reshape legal training and apprenticeships. Ivy brings a usual mix of insight, clarity, and energy. Read the full transcript of this episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_IvyGreyReturns.pdf

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 feeling “CLM fatigue” and what needs to change. We also talk about the future of legal education and how technology is reshaping everything, from pricing to professional training. It's a conversation full of her insight and refreshing, candid comments. Read the full transcript of the episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_LucyBassliReturns.pdf

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’s IP & Innovation Clinic, the only clinic in Georgia authorized by the US Patent and Trademark Office to allow law students to practice patent law. In our conversation, Nicole talks about how she found her way into legal education and why experiential learning is so essential for today's students. It's a must-listen as we gear up for the fall. Thank you very much. We’re back after the holiday with a new episode. This week, we're joined by Nicole Morris, professor of practice at Emory University School of Law, director of the Innovation and Legal Tech Initiative, and director of the TI:GER program. Nicole has had a fascinating, multifaceted career journey. After working as a chemical engineer for several years, she decided to go to law school. She then became a patent attorney at large and midsize law firms, and later worked in-house. As a professor of practice at Emory, Nicole's focus includes patent law, patent litigation, IP licensing, and strategy. She is director of the school's program Technological Innovation: Generating Economic Results (TI:GER). TI:GER is an innovative program that brings together graduate students in law, business, science, and engineering to work on ways to take innovative ideas from the lab to the marketplace. In our discussion, Nicole talks about her journey from chemical engineering to law, the various elements of TI:GER, and the importance of human skills in the legal profession. Read a transcript of this episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/BestofPioneers_NicoleMorris.pdf

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 highlights from her unique career path and offers practical insights on how the legal profession can better support holistic well-being. We thought it was a timely reminder of the importance of taking care of ourselves and each other. This week, we're joined by Denise Robinson, founding principal and belonging & well-being consultant at The Still Center, a consultancy that facilitates personal well-being, interpersonal connection, and organizational inclusion through mindfulness-based diversity and inclusion methods. Denise started her career as an employment litigator, focusing on discrimination claims and other employment disputes. She later changed career paths and became a global diversity and inclusion professional—serving as a law school and college admissions officer for Georgetown University, director of diversity and inclusion at O’Melveny & Myers LLP, and diversity officer at the International Monetary Fund. In her current role at The Still Center, Denise teaches contemplative practice techniques to lawyers and other professionals to promote self-awareness and authenticity, interrupt bias, and advance cultural humility. In our conversation, Denise speaks with us about how studying philosophy led her toward a legal career, what she learned as an L&E lawyer, the connection between DEI and well-being, and the challenges of managing global diversity initiatives. Read the full transcript of the episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_Bestof_DeniseRobinson.pdf

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 ultimately to a career dedicated to reshaping the legal profession. For nearly three decades, Reena has been advising top law firms, the Big Four, law companies, and general counsel on strategy and innovation. She's behind some of the most influential legal rankings and initiatives out there, including Chambers & Partners, the FT Innovative Lawyers program, and the RSG India report. In our conversation, Reena shares how she went from studying history to becoming a global voice for legal innovation. We talk about how her thinking around innovation has evolved, what trends she's watching now, and why many law firm leaders need a mindset shift to keep up with what's next. Read the full transcript of this episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_ReenaSenGupta.pdf

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 episode, Nicole talks about the transition of Theory and Principle into Factor, and what that's meant for her work. She also shares why it's important to be a healthy skeptic when it comes to new tech, how generative AI might improve access to justice, and what advice she has for anyone looking to build a career in legal tech. Read the full transcript of the episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_NicoleBradickReturns.pdf

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—Practical Law—back when the idea of legal know-how resources was still pretty foreign in the US. In our conversation, Ian shares what sparked that leap from practicing law to shaping how lawyers learn. We talk about what it was like introducing Practical Law to a skeptical market, how the pandemic reshaped training at Hotshot, and how younger generations are driving change in legal education. Read the full transcript of the episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_IanNelson.pdf

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 Association, advising startups, and writing her monthly Scaling Justice column for Thomson Reuters Institute. In this episode, Maya talks about her new role at the AAA, and how the organization is thinking about innovation—a fascinating case study on change management for a successful longtime organization. We also dig into the uneven landscape of AI oversight in dispute resolution, and hear her take on what's emerging and exciting in the world of justice tech. Read the full transcript of today's episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_MayaMarkovichReturns.pdf

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 foundation for Scrutinize. In our conversation, Oded shares how his work in the courtroom sparked the idea for the organization, what kind of feedback they've received, and what's next for Scrutinize. We also talk about the challenges and rewards of building something new in the legal space, and the advice he has for others thinking of doing the same. Read the full transcript of this episode here: https://www.seyfarth.com/dir_docs/podcast_transcripts/Pioneers_OdedOren.pdf

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