Pioneers and Pathfinders
Seyfarth Shaw LLP
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.
Episodes
Mentioned books

Jun 22, 2022 • 36min
Ivy Grey
Today’s guest is Ivy Grey, a legal tech entrepreneur, well-regarded writer, and former practicing lawyer. Her work on technology competence, ethics, and innovation has made her a respected thought leader in legal tech. Ivy has been recognized as a Fastcase 50 Honoree and was recently named to Women of Legal Tech by the ABA Legal Technology Resource Center. Currently, Ivy is Vice President of Strategy and Business Development for WordRake, an editing software for professionals. Ivy writes and speaks frequently about change management and legal technology implementation.
Listen in to today’s conversation to learn about how Ivy went from anthropology and journalism to bankruptcy law, the algorithm she used to choose a law school, and how swing dancing has influenced her major life decisions.

Jun 15, 2022 • 30min
Pieter van der Hoeven
In today's episode, we're joined by Pieter van der Hoeven. Pieter is the co-founder and CEO of Clocktimizer, which was one of the first legal tech products that applied machine learning techniques in an effort to pull actionable data from individual lawyer time records. An M&A lawyer by training, Pieter co-founded Clocktimizer out of frustration with a manual process of reviewing time records to report to clients and a belief that there had to be a better way. Over the years, Clocktimizer grew into a multimillion-dollar business with customers all over the globe. In April 2021, it was acquired by Litera, a legal tech company that helps legal organizations streamline operations, improve firmwide profitability, and build and scale pricing and legal management teams. Among other things, Litera itself has been on a bit of an acquisition binge in the legal tech space. Today Pieter is with Litera, where he continues to build on the successes of Clocktimizer and continues to work on the cutting edge of legal tech and its application to the profession.
Our conversation covered Pieter’s individual journey and how Clocktimizer arose out of an aha! moment when he realized that the rich data and timecards could be leveraged with automation. We also talked about his thoughts around the evolution of legal tech and its impact on profitability.

Jun 8, 2022 • 35min
David Johnson
David Johnson is a lawyer, teacher, and writer. His fascinating career path has taken him from Miami courtrooms in the '80s to general counsel roles for Silicon Valley tech startups in the '90s, and now teaching and research posts at Stanford Law School and the Stanford Institute of Design—known as the “d.school.” His work in design began as GC and COO for a consultancy that was applying design thinking for business advice. This eventually led to his d.school class, Negotiation by Design. Today, he is applying design thinking learnings, not just to the wicked problems facing legal, but to the even bigger problems facing climate change in his new book, Climate Activism by Design, which brings design thinking to citizen activists responding to the climate change crisis. His most recent article, “Design for Legal Systems,” was published by the Singapore Academy of Law.
Listen in to today’s conversation to learn more about how design thinking can help with the development and improvement of human systems, how it can help lawyers think more collaboratively, and how it can move us from the feeling of individual powerlessness to collaborative power to solve massive problems such as climate change.

Jun 1, 2022 • 31min
Jessica Stuart
Today we welcome Jessica Stuart, Senior Product Manager at Pro Bono Net. In her role, she combines her passion for access to justice with her interests in technology, process improvement, and the user experience to increase the effectiveness and reach of law firm pro bono programs via the practice management software Pro Bono Manager. Jessica has also helped lead the platform development and product strategy for Pro Bono Net’s Remote Legal Connect platform, which allows legal services providers, pro bono initiatives, courts, and community partners to rapidly build and manage a legal support program regardless of location. Jessica has been crucial in implementing the development strategy for Remote Legal Connect, which has been adopted by organizations such as Atlanta Legal Aid and Legal Aid of Nebraska.
Listen in to today’s conversation to hear more about the growth and evolution of Pro Bono Net, the power of virtual courtrooms to increase access to justice, how Jessica’s love of music got her started on the A2J technology path, and how SeyfarthLean was an early inspiration.

May 25, 2022 • 30min
Bob Ambrogi
For anyone following the rapidly evolving area of legal technology, today's guest will be a familiar voice. Bob Ambrogi—lawyer, journalist, media consultant, and blogger—has been working at the intersection of law, media, and technology for 40 years. He is known internationally for his expertise in legal technology, legal practice, and legal ethics. He's won numerous awards for his blog and his leading role on the cutting edge of change in the industry, including being named to Fastcase 50 and Legal Rebels Trailblazers. Before entering the blogosphere, Bob was an editor at a number of mainstream legal publications.
In today's conversation, we talk about Bob's journey as a journalist, his views on the current state of mainstream media, the potential of regulatory reform to further disrupt the industry, and the growing diversity of the legal technology industry.

May 18, 2022 • 37min
Ed Walters
Today we are joined by Ed Walters, a true pioneer in legal tech and driver of change in the legal industry. Ed is the CEO and co-founder of Fastcase, which has grown into one of the world’s largest cloud-based legal software providers for the legal industry. It currently serves more than 800,000 subscribers from around the world. Before founding Fastcase, Ed spent time in Big Law serving a number of large companies, and worked as a speechwriter in the White House. Ed is active in the A2J space, serving on the boards of Pro Bono Net, Public.Resource.org, Friends of Telecom Without Borders, and Salsa Labs. He also teaches Law of Robots, a class about the frontiers of law and technology, at Georgetown University Law Center. Ed is the creator of the Fastcase 50, a yearly list of 50 legal industry innovators who are drawn from all corners of the legal ecosphere. If you want to know who’s who and who’s coming up, it’s a can’t miss.
Listen in to learn how this self-professed “beer and softball lawyer” became an entrepreneur and founder of a pioneering legal tech company, how launching during the dot-com bubble burst worked out for him, and what’s next for Fastcase.

May 11, 2022 • 30min
Colin S. Levy
If you have spent any time in the “legal tech” hashtag on social media, you’ve probably encountered today’s guest. And you probably already know that Colin S. Levy is not your typical lawyer. Shaped by his experience graduating law school during the tail end of the Great Recession, he has taken many twists and turns, from eschewing Big Law to finding an in-house job—and most recently, taking on the role of legal tech evangelist at a contract life cycle management startup. Through it all, one of his key takeaways was that a lack of technological aptitude in lawyers was limiting the growth and evolution of the profession. And he has dedicated himself to exploring and closing this gap by finding out what makes legal industry innovators tick through his blog, podcasts, and social media.
Tune in to today’s conversation to learn more about Colin, his love of legal tech, and how he uses social media to create career opportunities for himself.

May 4, 2022 • 32min
Best of Pioneers and Pathfinders: Jeena Cho
In recognition of Well-Being Week in Law, we are bringing you our interview with Jeena Cho, a pioneer in the area of mental health and wellness for lawyers.
Long before the nonstop stressors of the last two years, Jeena Cho was a vocal advocate for the well-being of lawyers. It started when she realized how meditation and mindfulness could help her deal with the stress of practicing bankruptcy law. Since that time, her message about the urgency of wellness for lawyers has resonated throughout the industry, thanks in large part to her best-selling book, The Anxious Lawyer. She is a regular contributor to legal and traditional media, and she also speaks and offers training and workshops to law firms and bar associations around the country.
Listen in to today’s conversation to learn about:
- Jeena’s journey to law—which was inspired by a long-running TV show.
- How her meditation practice started.
- When she realized mindfulness had broader application to the well-being issues facing legal professionals, and how it can make the profession more inclusive.

Apr 27, 2022 • 33min
Michael Rynowecer
Today’s guest is Michael Rynowecer, president and founder of The BTI Consulting Group. For more than 30 years, Michael has helped service organizations enhance their performance by looking at every angle of the client relationship through the lens of the client experience. He has conducted and analyzed more than 20,000 one-on-one interviews with C-level executives to discover their expectations, needs, priorities, preferences, and opinions about outside counsel. This research has established BTI as the industry leader in delivering insights on how clients acquire, manage, and evaluate their law firm—and has been very influential in shaping how we think about client service today.
Join us today for a fascinating conversation on:
- How Michael's love of music helped him learn how to become a great writer.
- The impact of “the great resignation” on client relationships.
- His number one tip to improve client service post-pandemic.

Apr 20, 2022 • 34min
Stephanie Corey
Today’s guest is Stephanie Corey, a true pioneer in the field of legal operations. She started her career in business and finance, but became the first legal ops professional in Silicon Valley when she assumed that role for HP. She then co-founded and is a former executive member of the leading legal operations trade organization CLOC—the Corporate Legal Operations Consortium. Today Stephanie is a co-founder of UpLevel Ops, a consulting firm specializing in providing services for in-house legal departments and law firms.
Join us as we explore:
- The evolution of legal operations—from budgeting to a true business focus for legal.
- How the culture at HP created the perfect conditions for innovation in the law department.
- The role of serendipity in driving change.


