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

Lucy Bassli Returns

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

Jonathan Petts

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

Jordan Furlong Returns

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

Jason Marty

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

David Freeman Engstrom and Natalie Knowlton

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

Leslie Grandy

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

Best of Pioneers and Pathfinders: Leah Molatseli

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

Jack Cushman

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

Wendy Jephson

Our guest this week is Gus Neate. Gus is the CEO and co-founder of WilsonAI. WilsonAI, in turn, is a startup using AI to streamline legal operations for businesses. Gus is an Oxford graduate who began his career as an engineer before pivoting to law, working as a private equity lawyer at Clifford Chance. His diverse background also includes co-founding a tutoring company and working in product management at a legal tech startup. As an in-house lawyer, Gus witnessed firsthand the inefficiencies caused by repetitive legal tasks—an experience that continues to inspire his innovative work at WilsonAI.

Today, Gus shares how his engineering background shaped his approach to legal problem-solving, the journey of building WilsonAI, and his vision for how AI can empower legal teams. He also offers valuable advice for those entering the legal tech space.

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

Gus Neate

Pioneers and Pathfinders is a podcast about the people driving change in the legal industry. Interviews will focus on how their unique journeys inform their thinking about the profession, the business of law, the solutions they create, and where the industry is going next. The podcast will feature guests with multiple backgrounds and perspectives drawn from a number of areas including talent, technology, diversity and inclusion, social justice, education, training, and the business of law. The host of Pioneers and Pathfinders is J. Stephen Poor, chair emeritus of Seyfarth Shaw. During his 15 year tenure as chair and managing partner, the firm pioneered the application of Lean Six Sigma in legal service delivery. Today, he co-leads Seyfarth Labs, the firm’s technology research and development team and continues to serve as an advisor to firm leadership and as executive sponsor of strategic initiatives focused on innovation and growth. Steve brings his own experience as a legal industry pioneer to these conversations, resulting in insights that are both fascinating and instructive.

New tracks tagged #Innovator