Pioneers and Pathfinders

Memme Onwudiwe, co-founder of Evisort, shares insights on using AI for contract management and space law. He discusses founding Evisort at Harvard, teaching legal tech entrepreneurship, and his passion for African art and the metaverse.

Our guest today is Kathryn DeBord, vice president of product strategy at DISCO, a company that utilizes artificial intelligence, cloud computing, and data analytics to automate parts of the legal practice so that lawyers can focus their attention on other important areas. While Kathryn is known today for her work in legal innovation, her career journey actually began in an unexpected place—the Central Intelligence Agency. When Kathryn joined the CIA, she fulfilled a lifelong dream, but after four years as an intelligence analyst, she made a left turn and decided to go to law school. As a summer associate, Kathryn discovered her love for litigation, and went on to have a complex commercial litigation practice for over a decade. She was partner at Bryan Cave Leighton Paisner LLP when she joined the firm’s innovation committee, learning the ins and outs of law firm innovation and change management. Kathryn would go on to apply this knowledge as chief innovation officer, leading the firm’s international cross-disciplinary team to advance the quality of legal services through developing and adopting new technologies. Today, as vice president of product strategy at DISCO, she is helping the company determine what’s next in the litigation technology space. In today’s discussion, Kathryn tells us about how she started with the moniker “007,” leading to her life in the CIA; making left turns in her career; what litigation and innovation have in common; and working at DISCO.

Kristina Lambright is Senior Director of Strategic Growth at Perkins Coie LLP. She has had a fascinating legal career, serving various roles within the industry. After practicing in commercial litigation for nearly a decade, Kristina became a research specialist at Vinson & Elkins LLP, where she also assisted with budgeting. Seeking more involvement with driving decisions and revenue at the firm, she ventured into strategic pricing under the guidance of her colleague Toby Brown, the firm’s first director of pricing—and a friend of the podcast. Kristina went on to work at Akin Gump LLP, where she developed the firm’s strategic pricing and legal project management efforts. She has continued with pricing and LPM work at Perkins Coie, though her primary responsibility is leading the sourcing and acquisition of lateral partner candidates to meet the firm’s strategic goals. Additionally, Kristina is a founder and board member of the Legal Value Network, which drives deeper partnership and collaboration between legal organizations in order to accelerate the evolution of the industry. In our conversation, Kristina talks to us about her journey from commercial litigation to strategic growth, building trust with lawyers and clients, how she and her team at Perkins Coie approach lateral hiring, and how the Legal Value Network has grown since its inception.

As the freelance economy has grown over the past several years, more and more legal organizations and businesses have started seeking legal talent for fractional work in order to navigate budget restraints. Today’s guest, Matt Margolis, frequently discusses these developments as Head of Community at Lawtrades, a legal tech company that provides flexible, on-demand legal talent to in-house legal departments and law firms. Matt entered the legal industry as an attorney in private practice, but soon grew frustrated with the pressures of perfectionism. He started sharing his thoughts and stories on LinkedIn, and developed a sizeable following among legal professionals—eventually leading to an opportunity with Lawtrades. In his role, he leads the company’s efforts in marketing, business development, and community building. Matt is also the co-host of the Not Billable podcast and writes a newsletter, called Point Two, where he explores current events and hot topics in law. In today’s discussion, Matt talks to us about perfectionism among lawyers, his thoughts on the future of layoffs in the legal industry, and the challenges of pioneering a new way of sourcing legal talent.

Looking back over the past two years of guests, we see a diversity of backgrounds and perspectives: different generations, different paths, and different areas of focus—legal ops, legal tech, law education, working in the A2J space, and attorney well-being, among others. We've covered a lot of ground. Obviously, we cannot recap everything we have discussed, but as we think about change in the profession, certain themes seem to emerge from the conversations. For these purposes though, let's focus on the corporate legal landscape. The thesis of today’s episode is simple: That landscape has become more complex over the past few years—complexity only fueled by the pandemic. We tend to extol the virtues of simplicity, and rightly so, but complexity has its own virtue, opening both organizational and individual opportunities. Managing complexity is its own challenge, but in speaking with our pathfinders, we find certain markers of success.

To celebrate the two-year anniversary of Pioneers and Pathfinders, we welcome a very special guest—Professor Richard Susskind OBE. For those who have been engaged in the discussions around legal tech for the past few decades, Richard needs no introduction. He is one of the most advanced thinkers on the impact of technology on the profession, and has been challenging our notions about what it will mean to be a lawyer for a long time. Richard is an adviser, speaker, and author who was focused on legal tech and the future of the profession long before these subjects were top of mind in the industry. In the 1980s, he wrote his doctorate at Oxford University on artificial intelligence, and today, his main area of expertise continues to be the impact of AI and other technologies on the legal profession. Among other roles, Richard is President of the Society for Computers and Law, and Technology Adviser to the Lord Chief Justice of England and Wales. He is also an adviser to leading professional firms, in-house legal departments, and governments and judiciaries around the world. He is a frequent speaker at conferences, seminars, retreats, and other events, having been invited to lecture in more than 60 countries. Richard has written 10 books and has contributed more than 150 articles to The Times of London. His most recent publication is the third edition of Tomorrow’s Lawyers, which guides legal professionals through the imminent future of law, and calls upon the next generation of lawyers to embrace technology in order to improve current legal and court services. In our conversation, Richard discusses the ways we should all be thinking about legal innovation, the challenges of training lawyers for the future, and the qualifications of those likely to develop breakthrough technologies in law, as well as his own journey and how he became interested in AI as an undergraduate student.

Our guest today is a true legal tech expert—Dennis Kennedy, director of the Center for Law, Technology and Innovation at Michigan State University College of Law. Dennis first saw the potential that technology had for advancing the legal industry when he started using computer tools in his estate and tax practice. He went on to work in house at MasterCard, where he focused on information technology and supported the company’s mobile wallet, API, and Labs business groups. For more than 20 years, Dennis has been an advisor and consultant on innovation, legal technology, and productization. Since 2015, he has been a law professor, helping his students explore nontraditional career paths in legal tech. Additionally, Dennis has written hundreds of articles on topics such as legal technology, innovation, and law practice management, as well as co-authored four books. He is also a frequent speaker and has co-hosted The Kennedy-Mighell Report podcast with attorney Tom Mighell for over a decade. Today, Dennis talks to us about his journey from an estate and tax practice to legal tech, being one of the first attorneys with a professional website, how he creates a sense of value around technology in law school, and his thoughts on recent advancements in artificial intelligence.

Today we speak with John Alber—retired lawyer, businessperson, and legal futurist. Like many of our guests, John’s career path has taken some fascinating turns. He was a partner at Bryan Cave LLP when he was given the opportunity to buy a company, which ultimately became Alber Leland, Inc., a database and software publisher in the transportation sector. John would later return to Bryan Cave as Strategic Innovation Partner—one of the first in the industry—applying his business skills and experience to find innovative ways for the firm to deliver legal services through new technology. Over time, he developed what we now might consider one of the first captive ALSPs. Additionally, John was a futurist for the International Legal Technology Association, where he served as a consultant on different programs and helped the organization focus on business strategies. Today, John dedicates himself to conservation in Florida, particularly the Apalachicola River, which has been called America's most endangered wild river. In our conversation, John tells us about his experience innovating at Bryan Cave, the ways he convinced lawyers to adopt technology, the advice he would give to legal professionals on tech and innovation, and his recent conservation efforts.

As the current discussion around the hot topic of ChatGPT evidences, legal technology is constantly evolving and developing. This results in a level of complexity and confusion for both legal organizations and tech companies as they try to stay competitive. One of the people helping them navigate these waters is Zach Abramowitz, founder of Killer Whale Strategies. A former M&A attorney, Zach founded the company in 2019, with the goals of facilitating connections between law firms and tech companies, and assisting with their strategic decisions and investments. Zach’s interest in legal tech goes beyond his work at Killer Whale Strategies. He is an advisory board member at LegalMation, and he frequently blogs about the impact of technology on the legal industry. In our conversation, Zach talks about maintaining professional relationships through virtual meetings, what he looks for in clients and investment opportunities, and his thoughts on the potential impact of generative AI on the legal industry.

Today’s guest is Paula Davis, founder and CEO of the Stress & Resilience Institute, which helps legal professionals and teams manage stress and avoid burnout. Paula entered the legal profession as a real estate attorney, but facing burnout herself, she ultimately left her practice to pursue a master’s degree in Applied Positive Psychology at the University of Pennsylvania. There she began working in a program for the US Army, helping teach senior NCOs, officers, and other Army leaders and their families techniques to build resiliency. In 2013, she founded the Stress & Resilience Institute, where she has taught thousands of legal professionals and legal leaders tools associated with building individual, team, and organizational resilience by drawing on scientific studies and data. Additionally, Paula is a writer on topics such as stress management, burnout prevention, and hybrid teaming, frequently appearing in publications around the globe. She has also authored and co-authored a number of books and e-books. In today’s discussion, Paula tells us about being a self-described “recovering perfectionist,” how she defines resilience and burnout, and how legal organizations can maintain a sense of belonging in hybrid working environments, which both helps to build resilience and prevent burnout in law. In light of the growing complexity of the legal industry—and the stress associated with it, this is a timely and informative conversation.