Our guest today is Jimmy Vestbirk, founder of Legal Geek, an organization that hosts events around the world for the legal tech community. Jimmy started his career in business, owning and operating a number of online dating sites. As he ran into different legal issues in these ventures, his experiences ultimately inspired him to find solutions to these problems. Drawing on his business knowledge, he co-founded the legal startup Flex Legal, where he discovered his passion for events. Jimmy would go on to start Legal Geek with the goal of making legal tech events more fun and engaging—encouraging attendees to dress comfortably, learn from one another, and make friends rather than sell. Since launching in 2015, Legal Geek has reached a total of more than 50,000 attendees from over 150 countries. Legal Geek also organized the world’s first legal tech startup conference in 2016, and will host the brand new Legal Growth Geek conference focusing on legal tech adoption. In April, the Ministry of Justice in the UK awarded £3 million to Legal Geek and its partner CodeBase to accelerate the growth of legal tech through the program LawtechUK. In today’s discussion, Jimmy tells us about making the leap to the legal industry, hosting events during the pandemic, how Legal Geek has evolved since its first event in San Francisco, and the topics he's excited to hear about at the upcoming Legal Geek North America conference hosted in Chicago.

We’re joined today by John Grant, a legal operations strategist who works with law firms and legal teams to improve their capacity and productivity. A fourth-generation lawyer, John was in the technology industry for nearly a decade before he entered the legal profession. As an attorney, he started in in-house counsel and legal operations roles before founding Agile Professionals LLC in 2014. As a consultant, he helps legal professionals develop legal services that are profitable, scalable, and sustainable for themselves as well as the communities they serve. Additionally, John is board president of The Commons Law Center, a nonprofit law firm providing affordable legal services to those in Oregon who make up to 400% of the federal poverty level. Both Agile Professionals and The Commons Law Center incorporate Kanban, a methodology that aims to improve efficiency and achieve excellent client value in production processes by visualizing workflows. Today, John talks about what he learned from working in tech, the need for human connection in the A2J space, applying Kanban principles to legal organizations, and how he helps attorneys with overwhelming workloads.

Today we speak with our 100th guest, Catherine Jackson Moynihan, a true pioneer and expert in legal operations—and another great example of an allied professional driving change in the profession. Catherine is Senior Director of Strategic Intelligence & Advisory at Hyperion Research, an Epiq company. After working in product management roles for several years, she had the opportunity to join the Association of Corporate Counsel, where she started and directed the legal operation section—at a time when legal operations was not the established function that it is today. Among the numerous strategic initiatives Catherine undertook, one of her key accomplishments was developing the ACC Legal Operations Maturity Model, toolkit, and training. With mentorship from then-vice president of the ACC—and friend of the podcast—Susan Hackett, Catherine also led ACC Value Challenge (and its Value Champions awards), a program with the goal of identifying and disseminating leading practices in the industry. Today, Catherine oversees Hyperion Research, Epiq’s legal operations market intelligence program, and she spearheads practical guidance and engagement opportunities for global legal executives advancing their legal transformation efforts. In our conversation, Catherine discusses how she "wandered" into the legal industry, the importance of data in Epiq’s legal services management framework, training legal professionals on change management, and her research work. As always, we appreciate your time listening in on these conversations. Now, on to the next 100 guests!

As we’ve discussed many times on the podcast, the access to justice gap is a particularly complex challenge to address, due to its links to systemic issues such as poverty and limited availability to legal resources and technology. Today’s guest, however, is helping people overcome these broader obstacles to legal services. Amanda Brown is the founder and executive director of Lagniappe Law Lab. The organization’s mission is to facilitate access to justice at scale for Louisiana's underprivileged populations through the use of technology, human-centered design, and operations principles. Upon graduating law school, Amanda was a disaster recovery attorney, using technology to assist victims of disasters with accessing public benefits and title clearing. She then worked as a Microsoft NextGen Fellow for the American Bar Association’s Center for Innovation, helping support the design and development of the Legal Services Corporation’s legal navigator program, which connects those in need with legal resources available to them. She went on to serve as a legal technology consultant for the Louisiana Bar Foundation on its statewide triage portal. Drawing on these experiences in legal tech and the A2J space, Amanda founded Lagniappe Law Lab in 2019. She is also co-chair of Louisiana’s Access to Justice Commission’s technology subcommittee, and she is a member of the Legal Services Corporation’s Emerging Leaders Council. Today, Amanda tells us about Lagniappe Law Lab—and how the team is incorporating human-centered design in its work, the unique challenges that the Lab’s clients face in Louisiana, and how she entered the A2J path.

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.