The New Architecture of Legal and Compliance with AI

In this episode of Great Women in Compliance, Dr. Hemma R. Lomax speaks with Sam Flynn, co-founder of Josef, about the transformation of legal and compliance functions through technology. They discuss the importance of human-centered design, the role of AI in legal architecture, and the need for trust in AI tools. Sam shares his journey from creating Myki Fines to building self-service legal solutions that bridge the access-to-justice gap. The conversation emphasizes the importance of user experience, governance practices, and the need to rethink traditional professional roles in the legal field. Takeaways: Legal and compliance functions must evolve to be more human-centered. AI can significantly enhance legal decision-making processes. Trust in technology is crucial for successful implementation. User experience should be prioritized in legal tech solutions. Automation can free up valuable time for legal professionals. Access to justice is a critical issue that can be addressed with technology. Rethinking traditional roles in law can lead to better outcomes. Data-driven insights can improve compliance practices. Collaboration between experts and end-users is essential for success. Legal technology should focus on delivering real value to users. Sound Bites: "AI should unleash human potential." "Trust is the key to unlocking value." "We need to build trust in our technology." Chapters: 00:00 Introduction to Legal Transformation 02:32 The Journey of Sam Flynn and Mickey Finds 05:30 Rethinking Legal Systems and Design 08:10 Substance Over Form in Legal Processes 10:56 The Role of AI in Legal Architecture 13:39 Building a Legal Front Door 16:24 User Experience in Compliance 18:54 Engagement and Data Utilization 21:56 The Future of Legal Workflows 24:29 Deciding Between Automation and Human Input 26:56 Navigating High-Risk Inquiries 27:50 Strategic Automation for Stakeholder Engagement 28:58 The Importance of Human Expertise in AI 30:57 Transforming Fear into Opportunity with AI 32:59 Building Trustworthy AI in Legal Settings 36:56 Governance Practices for AI Deployment 43:51 Access to Justice: Bridging Gaps with Technology Guest Biography: Sam Flynn is the Co-Founder and Chief Operating Officer of Josef, a legal automation platform that empowers legal and compliance teams to create reliable, self-serve tools — no coding required. In his role, Sam leads Josef’s business operations, governance, marketing, and customer success functions, scaling both product impact and organizational trust. An ex-BigLaw litigator and experienced legal technologist, Sam has long been passionate about using technology to bridge the access-to-justice gap and elevate the delivery of legal services. In 2016, he built Myki Fines, a public-facing legal tech solution that attracted more than 60,000 users in its first month and helped catalyze reforms to unfair laws. At Josef, Sam combines legal expertise with product and operational leadership to help teams rethink how legal and compliance work gets done — shifting from inbox-driven bottlenecks to strategic architectures that deliver decision-useful guidance at scale. He is a frequent speaker on generative AI in legal, a board member of the Center for Legal Innovation, and an advocate for human-centered legal design.