Pioneers and Pathfinders

Ashley Carlisle, CMO at HyperDraft, discusses generative AI's impact on legal innovation, streamlining document processes in healthcare, their invite-only platform's approach to client onboarding, AI technology adoption in the legal industry, transitioning from lawyer to entrepreneur, and the influence of generative AI on the legal field.

Our guest this week is a leading voice on the future of legal education and law practice. Andrew Perlman is Dean at Suffolk University Law School, and has been a professor there since 2001. Before entering academia, Dean Perlman was a litigator with a lifelong fascination with innovation and technology. He has served several important functions in the American Bar Association, and was recently appointed to serve on the Advisory Council of the ABA Task Force on the Law and Artificial Intelligence. Dean Perlman has also been involved in various national and local reform efforts—from police practices and access to justice, to developing alternate paths to law school and bar admission. He has served as a member of the Content Scope Committee of the National Conference of Bar Examiners, which helped to identify content for the next generation of the bar exam. Additionally, he has written numerous articles on professional responsibility and legal innovation, and he has served as a presenter or panelist at more than 100 academic, judicial, and other professional programs. Today, Dean Perlman talks about how his passion for innovation started with a Commodore 64, the history and culture of Suffolk, helping law students embrace generative AI, and updating the bar exam.

Today we are joined by Flo Nicolas, a self-described “nonboring lawyer.” Flo is co-founder and chief operating officer at DEI Directive, a technology company helping organizations shape the future of work through inclusive and innovative practices. Flo began her career as legal counsel at various law firms and companies. She then worked in the telecommunications industry for several years. Later, Flo had the opportunity to join How to Contract, a training and development resource for lawyers. There she served as Chief Growth and Community Officer and hosted Contract Tech Showcase, a video series aimed at educating people on legal tech. Flo went on to create two local TV shows, Get Tech Smart and Get Resource Smart, which she also directs, produces, and hosts. These programs shine a light on New Hampshire’s tech startup community and organizations that provide vital resources to residents in need. In 2023, Flo was named one of New Hampshire Business Review’s “Outstanding Women in Business” and won Blaze Group’s Best In Business Award for “Best in Tech & Web3.” In our discussion, Flo talks about what organizations should measure in their DEI initiatives, the ways that law firms can leverage technology to foster diversity, her passion for negotiation, and how she developed her social media skills.

This week, we speak with Anusia Gillespie, Chief Strategy Officer at SkillBurst Interactive, a company providing on-demand learning to Am Law 200 firms, global legal organizations, and public-sector agencies, among other clients. Anusia has both an MBA and JD from Boston College, and has worked in various functions throughout the legal ecosystem—law firm practice, academia at Harvard Law School Executive Education, law firm business as the first Head of Innovation at Eversheds Sutherland, and in-house service transformation at the law company UnitedLex. At SkillBurst Interactive, Anusia is responsible for the expansion of digital training and upskilling in order to help the global legal industry thrive as technology continues to evolve. Additionally, Anusia has received the Fastcase 50 Award for being a visionary and an influencer in the legal industry. Today, Anusia discusses making the decision to pursue business, the benefits of not having a defined job description, the common thread of her career, and how law firms should approach talent development.

Today we are joined by Mary O'Carroll, a true pioneer and pathfinder in the legal industry. Mary is Chief Community Officer at Ironclad, a leading contract lifecycle management program for innovative companies. She started her career in business development and consulting before joining Orrick, Herrington & Sutcliffe LLP in a finance role. Her work soon transitioned into a legal operations role—a function that was practically nonexistent in law firms at the time. Mary was later hired by Google, where she built and managed the operations of the legal department as the Director of Operations, Technology, and Strategy. While at the company, she co-founded the Corporate Legal Operations Consortium (CLOC), a global community dedicated to transforming the business and practice of law. Mary continues her mission to drive change in the legal industry. She is a frequent public speaker and media contributor, and she hosts the Ironclad podcast Pearls On, Gloves Off. In our wide-ranging discussion, Mary tells us about her unexpected entry into the legal field, the origin story of CLOC, how generative AI may change legal ops, and what excites her about joining Ironclad.

For our last episode of the year, we welcome Dr. Ron Dolin, chief innovation officer at ODR.com. Dr. Dolin has had a fascinating and dynamic professional journey. A math and physics major, he began his career at the high-energy physics lab CERN in Geneva. He went on to earn a PhD in computer science and became one of the first 100 employees at Google, where he worked for several years. Having a deep interest in morality and ethics, Dr. Dolin then decided to go to law school and pursue the legal path. He became a law professor and has taught legal tech courses at Stanford, Notre Dame, and Harvard. Today, Dr. Dolin works with ODR.com to understand how AI can help the dispute resolution field improve its quality of services. In addition, he is a private investor in legal tech startups. In our discussion, Dr. Dolin speaks about going from Google to law, his love for teaching, the importance of quality metrics as lawyers use generative AI, and his work at ODR.com.

This year, our virtual roundtable series has explored the implications of generative AI and natural language processing models in the legal industry. Our first roundtable covered the risks and benefits of generative AI, while the second addressed the AI technology landscape and implementation strategies. Now, in our third installment, our esteemed panel—Lorie Almon, Chair and Partner of Seyfarth Shaw LLP; Anusia Gillespie, Chief Strategy Officer at SkillBurst Interactive; Jennifer Leonard, Founder of Creative Lawyers and Adjunct Professor at the University of Pennsylvania Law School; and Andrew Perlman, Dean and Professor of Law at Suffolk University Law School—focused on lawyer formation and attorney development in the age of artificial intelligence. Our panelists explored how law schools, law firms, and corporate legal departments can shape the lawyers of tomorrow. We discussed the importance of teaching empathy in law school, the impact of generative AI on task-based learning, training more experienced lawyers on new technology, as well as the incentives and training structures needed for all legal professionals in a different environment.

Damien Riehl, Vice President and Solutions Champion at vLex, discusses vLex's new product Vincent AI, crafting arguments using real cases, confidentiality concerns in AI training, the importance of common tagging methodology, and the 'All the Music' project that generated billions of melodies to protect against copyright infringement.

Julie Saltman, Co-founder and CEO at Standd, talks about how AI helps lawyers save time in due diligence, the lessons she learned with the launch of the company, and the impact of generative AI on legal writing.

As technology has progressed, we have also seen emerging concerns for freedom of speech and privacy. Our guest today has spent the past 30 years defending individual liberties in the digital space. Cindy Cohn is the executive director at the Electronic Frontier Foundation (EFF), the leading nonprofit organization ensuring that technology supports freedom, justice, and innovation for all people. She started her career as a civil litigator in private practice, where she handled various cases related to technology. Then, in 1993, the EFF offered her the opportunity to serve as outside lead attorney in the case Bernstein v. Dept. of Justice, the successful First Amendment challenge to the US export restrictions on cryptography. Today, she handles legal matters involving NSA spying, platform censorship, and surveillance technologies, among other issues. Cindy has received numerous awards and honors for her work. In 2020, she was included in The Nonprofit Times Power and Influence Top 50 list, honoring movers and shakers. In today’s discussion, Cindy talks about the fascinating origins of the EFF, how she became involved in human rights work, how her practice has evolved over the years, and her strategies for protecting people's privacy.