Careers and the Business of Law

The way litigation has been practiced for decades is cracking - and the lawyers who see it first will win. Recorded live at Legalweek 2026, host David Cowen sits down with Jeffrey Chivers , CEO of Syllo, to unpack why AI isn't just automating legal tasks - it's collapsing the traditional litigation workflow entirely. The path from discovery to trial-ready strategy is getting shorter. The question...

What happens when AI meets one of the most risk-sensitive professions in the world? In this episode, David Cowen sits down with KPMG partner Ed Gill to unpack how AI, operating models, and contract intelligence are reshaping the business of law. The real shift isn't just new tools - it's a new mindset where lawyers move from doing the work to orchestrating humans, workflows, and AI agents. Hosted...

What happens when AI gets powerful, but verification becomes the bottleneck? In this candid, end-of-year conversation,  Clearbrief Founder & CEO Jacqueline Schafer breaks down why accuracy, sourcing, and trust - not raw model power are the real constraints on legal AI adoption today. Listeners walk away with a clear mental model for where AI actually delivers ROI in law firms and corporate legal t...

Regulators finally caught up to how business actually happens: over text, WhatsApp, and mobile apps. In this year-end conversation, David Cowen sits down with Matt Rasmussen , Founder of ModeOne , to unpack why off-channel mobile data has become a $6B compliance problem and a massive opportunity for legal, IT, and ops professionals. Listeners will walk away with a clear view of where regulation is...

In a rare, candid roundtable, five of the most influential Chief Innovation Officers in Big Law join  David Cowen to reveal how their roles and the entire legal industry have transformed in just the last 18 months. This episode pulls back the curtain on the strategic, operational, and cultural shifts that are redefining how modern law firms operate. From AI adoption to talent design to client co-c...

Steno 's COO, Prabhdeep Singh joins David Cowen to break down why 2025 was the year AI finally got real in legal and what that means for 2026 and beyond. They explore how Steno is turning "data exhaust" into strategic advantage, why outsiders are reshaping the business of law, and what talent will define the next era. This episode is a roadmap for anyone looking to move from now to next in a rapid...

In this episode of Careers and the Business of Law, David Cowen explores a provocative idea: every billion dollars invested in AI and infrastructure generates an exponential surge in legal work. So what does that mean for the future of legal careers, legal operations, and the business of law? Joining David are Omar Haroun , Founder and CEO of Eudia, and Alison Zoellner , Group General Counsel at D...

In this Careers and the Business of Law | Pre-TLTF Series episode, David Cowen sits down with James Ding , CEO and Co-Founder of DraftWise and former Palantir engineering lead, to explore how data, accountability, and forward-deployed engineering are reshaping the business of law. From mobilizing firm knowledge to the philosophical lessons behind "Stillness is the Key," James shares a rare blend o...

In this Careers and the Business of Law | Pre-TLTF Series conversation, David Cowen sits down with Tim Follett , Founder and CEO of StructureFlow, to explore how visual intelligence and AI agents are reshaping how legal and financial professionals work with complex data. From turning static charts into dynamic, interactive systems to teaching AI to see structures the way lawyers do, Tim shares a c...

In this Careers and the Business of Law | Pre-TLTF conversation, David Cowen sits down with Tom Dreyfus , CEO and Founder of Josef, to unpack what it really takes to build and scale a legal tech startup from the ground up. From the first Legal Tech Fund investment to today's thriving TLTF community, Tom shares unfiltered insights on grit, growth, and redefining success beyond the 9-9-6 grind. Key...

In this episode of Careers and the Business of Law, Pre TLTF conversation, David Cowen sits down with Dr. Hemma Lomax , Deputy General Counsel at DocuSign, to explore how intelligent agreement management is transforming legal operations and compliance. From turning static contracts into data-rich insights to empowering legal teams as strategic business partners, Hemma shares how technology, ethics...

In this episode of Careers and the Business of Law - Legal Data Intelligence seriese, David Cowen sits down with Odette Claridge (ProSearch), Tara Lawler (Morgan Lewis), and Virginia Ring (Kilpatrick Townsend) to unpack how Legal Data Intelligence (LDI) is transforming mergers, acquisitions, and divestitures. They share how data governance, AI, and collaboration are reshaping due diligence and dea...

In this episode of Careers and the Business of Law, David Cowen sits down with Nathan Reichardt , PwC's Lead Managed Services Director and AI Champion, for a conversation that bridges technology and humanity. They unpack why "observability" isn't just a technical concept, it's the foundation of trust in an age of autonomous agents. From building glass-box systems that make AI accountable to recogn...

What happens when AI gets faster than your legal team? In this episode, we're pulling back the curtain on the real disruption happening inside law firms, legal departments, and software giants. Microsoft's E.J. Bastien and Relativity's CTO Keith Carlson join David Cowen for a no-holds-barred conversation on AI's impact on legal strategy, workflows, careers and how everything is being redefined. If...

What separates a legal department that saves money from one that builds competitive advantage? Two powerhouse CLOs, Rishi Varma (Cargill) and Tim Fraser (Toshiba America) - sit down with David Cowen to unpack the shift from legal risk managers to business growth drivers. If you're a legal leader, strategist, or tech-savvy operator, this is essential listening. The future isn't coming. It's here. A...

Hosted by David Cowen | Presented by Steno Live at ILTACON 2025, in this candid conversation, Shannon Bales , Litigation Support Senior Manager at Munger, Tolles & Olson, shares how he's preparing his team for the AI-driven future, by turning ticket-takers into consultants. From tools like ChatGPT, Copilot, Harvey, and Claude, to the foundational skills that matter most (language, curiosity, and c...

Hosted by David Cowen | Presented by Steno What does it take to get in "the room where it happens"? Melissa Faragasso , a fifth-year associate at Cleary Gottlieb, didn't wait for permission - she stepped forward, made the ask, and landed a secondment to the firm's innovation team led by Ilona Logvinova. Live from the floor at ILTACON 2025, in this candid conversation, Melissa shares how a passion...

Hosted by David Cowen | Presented by Steno Live at ILTACON 2025, in this wide-ranging conversation with Stephen Dooley , Director of Electronic Discovery and Litigation Support at Sullivan & Cromwell, we dig into the new rhythm of legal tech, how it's evolving, where the real value lives, and why the smartest professionals are not chasing AI, they're designing with it. From creative use of ChatGPT...

Hosted by David Cowen | Presented by Steno Live from the floor at ILTACON 2025, in this rich, retrospective conversation, Phil Bryce , longtime legal Knowledge Management leader and strategist - traces the evolution of legal tech from the dawn of email to today's GenAI disruption. But this episode is about more than just tech. Phil shares hard-earned lessons on connection, courage, and how relatio...

Hosted by David Cowen | Presented by Steno Live at ILTACON 2025, Rachel Shield Williams , Director of Client Intelligence at Sidley Austin, breaks down how the smartest legal teams are using AI, not just to save time, but to build stronger relationships, drive smarter decisions, and unlock entirely new ways of working. From ChatGPT to lakehouses, Rachel shares how the future of legal operations is...

Hosted by David Cowen | Presented by Steno Live from ILTACON 2025, this episode features a candid, heart-forward conversation with Melanie Prevost , Senior Director of IT Infrastructure & Technical Support at Vinson & Elkins. Melanie shares how GenAI is empowering neurodiverse professionals, reducing barriers to productivity, and creating real inclusion, not just policy-driven but experience-based...

Hosted by David Cowen | Presented by Steno Live from the floor at ILTACON 2025, this episode dives into the real transformation happening inside law firms and what GenAI has to do with it. Julie Brown , Director of Practice Technology at Vorys, shares why attorneys are finally asking for AI, what it means to build digital agents, and how legal tech professionals have evolved from taskmasters to st...

What if one judge kills GenAI in court? Former U.S. Magistrate Judge Andrew Peck says it could set legal innovation back a decade. In this episode, David Cowen and co-host Nicole Giantonio go inside the mind of the "Godfather of eDiscovery" to unpack the real risks, courtroom landmines, and what every lawyer needs to know before using AI in a case. This isn't theory. It's already happening. What Y...

Hosted by David Cowen | Presented by Steno Live from the floor at ILTACON 2025, this episode cuts through the hype and gets into the real AI tools and workflows legal professionals are using right now. Stephanie Clerkin breaks down how GenAI is supercharging court reporting, unlocking billable time, and why "context engineering" may be the most important skill of your career. If you're curious, ov...

Will Seaton , Chief Customer Officer at DraftWise and former commercial lead at Palantir sits down with David Cowen to unpack what's really changing at the intersection of AI, contracts, and legal careers. This conversation dives deep into the shift from prompt to context engineering, the rise of roles like forward deployed engineers, and why the future of legal work isn't about replacing lawyers,...