Funding Legal's Future: As Legal Tech Matures, What Attracts Investors? (Yelena Shkolnik - Jump Capital)

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.

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.

In advance of this year's RelFest in Chicago, Aron Ahmadia, Vice President of Applied Science at Relativity, joins the podcast to discuss AI evaluation, AI benchmarking and the transition from traditional Technology Assisted Review (TAR) to generative AI in legal document review and eDiscovery. The conversation covers the daily operations of a global AI team, the concept of "evaluation as a product," and the methodology behind testing large language models (LLMs) for legal tasks. Aron also discusses a recent study that compared the accuracy and efficiency of TAR and human document review against Relativity's generative AI tool, aiR for Review. Aron talks about: A day in the life of the VP of Applied Science at Relativity.

Emily Logan Stedman, commercial litigator at Husch Blackwell, discusses moving beyond the billable hour not just to modernize legal billing but to also prioritize lawyer well-being. The conversation explores the practical steps required to transition traditional litigation models toward Alternative Fee Arrangements (AFAs). Emily details her methodical approach to utilizing secure legal AI tools to analyze historical time entries, allowing her to offer phased flat fees, strategic counsel subscriptions, and predictable contract review pricing. The discussion also covers strategies for maintaining mental health in demanding legal environments, taking control of chaotic schedules, and reframing the billable hour as a tool for career management rather than a burden. Things We Talk About in this Episode Emily's transition from bankruptcy law to general commercial litigation after moving to Wisconsin.

In this episode, Justin Wales, Chief Legal Officer for Crypto.com makes a second visit to the podcast. This time around, he discusses his new book, The AI Legal Handbook, the emerging regulatory landscape, liability frameworks, and practical applications of artificial intelligence. Justin outlines how attorneys and regulators should approach modern AI models, the mechanics behind AI, and the effect of generative AI on legal education. The discussion covers key regulatory principles, the balance between strict liability and negligence frameworks, copyright issues in machine learning training, and the governance challenges of artificial general intelligence (AGI). Things We Talk About in this Episode Transitioning from cryptocurrency regulation to developing a unified framework for artificial intelligence law