Technically Legal - A Legal Technology and Innovation Podcast

In this episode of Technically Legal, Jay Madheswaran, CEO of Eve, discusses his career path from the early days of Facebook to becoming a VC and investing in artificial intelligence. His stint as a VC eventually led to the creation of the legal technology platform Eve. The episode explores how Eve utilizes artificial intelligence to assist plaintiffs attorneys with tasks such as case management, drafting demand letters, and processing client intakes. Jay explains how software automation can optimize client outcomes by accelerating routine legal workflows which benefits the contingency-based economic model of plaintiff law firms. Key Segments Jay details his early career experience at Facebook and his subsequent transition into venture capital with a focus on artificial intelligence investing. The discussion covers the initial founding of Butler Labs and the strategic pivot toward building artificial intelligence solutions specifically for the legal industry. Jay outlines the economic structure of plaintiff law firms, noting that their contingency fee models require high efficiency and leverage to remain profitable. The conversation shifts to EveOS and how the software assists attorneys by automating the review of massive medical records and drafting demand letters for personal injury cases. Jay introduces Eve Intake, an automated voice AI agent that handles client calls and gathers initial case information. The episode concludes with a discussion on Eve's Atlas data platform, which structures firm data to make it highly accessible for future legal work. Episode Credits Editing and Production: Grant Blackstock Theme Music: Home Base (Instrumental Version) by TA2MI

We welcome back Sabastian Niles, President and Chief Legal Officer at Salesforce, to discuss his recent "Open Letter to Law Firms." As the legal industry hits a critical inflection point, Sabastian argues that the era of "AI theater" and small-scale pilots is over. The conversation dives deep into the Innovator's Dilemma facing law firms, the shift toward agentic AI, and how firms must reimagine their business models to remain competitive. Sabastian highlights that legal professionals are uniquely positioned to lead the charge in trusted AI transformation, provided they embrace transparency, data integration, and shared efficiency gains with their clients. Specifically, he offers four systems law firms and other service providers must establish if they want to succeed in the AI era: System of Engagement: A unified digital interface that replaces fragmented tools with seamless, real-time collaboration between firms and clients. System of Agency: An ethically governed AI framework that scales firm capacity and reimagines service delivery while maintaining strict human oversight and compliance. System of Work: A trusted, enterprise-grade platform that integrates daily professional applications into a cohesive, high-performance workflow. System of Context: A secure "single source of truth" for client data that ensures strategic counsel is grounded in history while protecting attorney-client privilege. Other Things We Talk About in this Episode The End of the Pilot Era: Moving beyond experimentation to integrated, unified AI platforms is no longer optional—it is a prerequisite for competitiveness. The Relationship Challenge: AI should be used to break down internal silos, allowing firms to bring their "tribal knowledge" and collective intelligence to every client engagement. System of Agency: A shift from manual workflows to "agentic" systems where AI agents handle triage, research, and routine queries (e.g., Salesforce's Outside Counsel Support Agent). Value-Based Evolution: Law firms must navigate the friction between the billable hour and AI-driven efficiency by focusing on superior outcomes and shared savings. Trust as Propulsion: In legal services, trust isn't just a guardrail; it's a growth lever. Mastering "Trusted Agentics" ensures human-aligned AI that respects privilege and confidentiality.

Aron Ahmadia, Relativity’s VP of Applied Science and a PhD mathematician, explores how legal AI is tested and benchmarked. He compares traditional TAR with generative review, explains the rise of “evaluation as a product,” and discusses private benchmarks, human versus automated assessments, review economics, and what AI adoption may preserve as the technology evolves.

Emily Logan Stedman, a Husch Blackwell commercial litigator and lawyer well-being advocate, explores life beyond the billable hour. She discusses sustainable careers, strategic counsel subscriptions, phased flat fees for complex litigation, and using secure AI to analyze billing data and build profitable pricing models. The conversation also covers boundaries, deep work, and making legal costs more predictable.

Justin Wales, Chief Legal Officer at Crypto.com and author of The AI Legal Handbook, specializes in technology law and governance. He discusses emerging AI regulation, liability frameworks like negligence versus strict rules, how lawyers should grasp model mechanics, generative AI’s impact on legal education, IP and training-data questions, and governance challenges posed by future AGI.

April Miller Boise, a seasoned corporate attorney and former Intel Chief Legal Officer, reflects on moving from law firm leadership into in-house strategy. She discusses differences between running firm P&L and corporate legal teams. Conversation covers manufacturing and supply chain experience, expectations for law firms using AI, and traits modern legal talent should cultivate.

Vivienne Ming, theoretical neuroscientist, entrepreneur, and author of Robot Proof, explores AI augmentation over automation. She discusses human-AI collaboration, the Polymarket forecasting study, well-posed versus ill-posed problems, labor disruption, and the role of endogenous motivation and teachable traits in building adaptable professionals.

Rebecca Anderson, Head of Legal EMEA at Microsoft, shares how she led AI rollout inside a global legal team. She explains the three-phase AI framework and using AI triage with paralegals to scale support. She discusses changing expectations for law firms and the skills lawyers need as AI shifts work toward higher-value legal judgment.

Laurence Brown, Partner at EIP and head of Visser AI, is a patent attorney with an electrical engineering background and 25 years of experience. He discusses what it means to be AI-native, how Visser AI redesigns patent workflows for speed and fixed-fee economics, why specialist patent AI outperforms general LLMs, and how AI reshapes attorney roles and client expectations.

Tyler Foreman, VP of AI at Rocket Lawyer with a background from Intel and DocuSign, explains how AI can democratize legal help for individuals and small businesses. He discusses using generative models as a legal operating system, Rocket Copilot’s role in contract review and plain-English risk summaries, and the balance between AI assistance and human escalation.