Careers and the Business of Law

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-creation, this conversation uncovers the real work happening inside elite firms and why the next decade of legal will look nothing like the last. If you want to understand where legal innovation is actually headed (beyond the hype), this is the episode. Featuring: Gina Lynch (Paul Weiss) David Wang (Cooley) Joe Green (Gunderson Dettmer) Annie Datesh (Wilson Sonsini) Matt Beekhuizen (Greenberg Traurig) KEY TOPICS COVERED How the CINO role moved from back-office function to firmwide strategic leadership Why GenAI forced a shift from point solutions to holistic, systems-level strategy The rise of client co-creation and why CINOs now spend more time with clients than ever What tech is showing real promise and what's still overhyped The biggest mistake clients make when implementing AI The new talent model: multidisciplinary teams, communication skills, and radical curiosity What future legal leaders need to understand about innovation careers 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ Never eat alone!  

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 rapidly shifting industry. Key Topics Covered How AI shifted from "shiny object" to budget line item and how that changed client expectations overnight. Why the real competitive edge isn't the model you use, but the data and distribution you control. The outsider advantage: lessons Prabh brought from Uber, WeWork, and Clover Health into legal tech. Inside-out vs. outside-in innovation and why blending both is the only sustainable path. Why trust, not technology, still wins deals in a crowded legal tech landscape. The rise of the "core four": how internal evangelists drive firm-wide adoption and culture change. Predictions for 2026–2027: industry shakeouts, left-field entrants, and the next wave of legal transformation. 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ Never eat alone!  

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 Dentsu Global. Together, they unpack how global AI investment is reshaping legal demand, talent models, and the very definition of what lawyers do. They address a critical misconception: while some focus on potential job loss, the real story may be the opposite. Massive AI and data infrastructure expansion is unlocking legal complexity across real estate, IP, regulatory structures, tax, contracting, and global compliance - creating far more legal demand than traditional models ever anticipated. Omar explains why pairing engineering talent with elite legal judgment is becoming the new competitive edge, while Alison brings the in-house perspective on responsible leadership, managing disruption, and preparing teams for the work AI is actually creating. This conversation goes beyond automation to ask a bigger question: if every wave of AI investment multiplies legal work, are we entering the largest legal growth cycle of our lifetime? Key Topics Covered Why AI infrastructure investment is driving legal demand The shift from time-based work to outcome-driven value Lawyers plus AI engineers as the core legal team Breaking down silos to build integrated decision systems Responsible leadership and preparing talent for change 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ Never eat alone!  

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 of technical insight and human wisdom ahead of the TLTF Summit in Austin. Key Topics Covered: How DraftWise turns legal data into actionable intelligence through digital twins of firm knowledge. The difference between a consultant and a forward-deployed engineer and why accountability is the real differentiator. Lessons from Palantir's customer-first model and how it inspired a new standard in legal AI. Why TLTF feels like a Michelin-star experience - a curated mix of funders, founders, and innovators. How cross-generational collaboration is driving innovation across law and tech. What James is reading and how "Stillness is the Key" informs his leadership philosophy. Why focus is more valuable than information in the age of AI abundance. 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ See you at TLTF!  

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 clear, forward-looking view of the next chapter in legal tech and what he's launching on the TLTF stage in Austin. Key Topics Covered: How visualization unlocks cognitive power in complex legal and corporate structures. Tim's AI-first workflow at StructureFlow, from meeting transcripts to intelligent summaries. Why personal knowledge management (PKM) and visual databases are the next frontier for professionals. The shift toward agentic and digital workforces and how StructureFlow is applying them today. Why 2025 is the year of AI generalists, and 2026 will belong to domain-specific innovators. How forward-deployed engineers and domain experts are changing the client experience. A sneak peek at StructureFlow's new brand and vision, launching live at the TLTF Summit. 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ See you at TLTF!  

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 Topics Covered: The founder's journey: how Josef became the Legal Tech Fund's first portfolio company. Why relationships and listening matter more than capital in startup growth. The evolution from outsider to insider in the TLTF community and what that feels like. Why there are no shortcuts in building a meaningful business or reputation. The balance between grit and grace, navigating startup life and parenthood. How TLTF built a warm, human-centered community in an industry full of transactional events. A reflection on privilege, partnership, and progress in modern leadership. 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ See you at TLTF!  

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, and leadership intersect in this new era of legal intelligence. Key Topics Covered: How DocuSign evolved from e-signatures to intelligent agreement management. The "agreement trap" and how legal teams can unlock trapped value in contracts. Why legal and compliance professionals should focus less on data entry and more on strategy. The rise of Legal Data Intelligence (LDI) and how it's reshaping the business of law. Insights from DocuSign's acquisition of Contract Nerds and what it means for the future of collaboration. Why being "in the arena" matters more than perfection, lessons from leadership and podcasting. The Davos of Legal Tech: what to expect from the TLTF Summit and the innovators shaping it. 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ See you at TLTF!  

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 deal execution and why frameworks like LDI's toolkit are now must-haves for modern legal teams. Key Topics Covered: How LDI's corporate working group built the first data-driven toolkit for M&A and divestitures. Why today's M&A landscape is defined by the 3 Vs of data, volume, variety, and velocity. Practical steps for maintaining data integrity and audit trails across multiple corporate entities. The new reality: collaboration between legal, IT, privacy, and compliance is non-negotiable. How crowdsourcing best practices across firms accelerates learning and innovation. What the Architect Program offers for professionals eager to shape the next wave of legal data frameworks. A look ahead: AI governance and ethical frameworks as the next frontier for legal data professionals. 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ Never eat alone!  

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 recognizing the invisible pressures on professionals, this discussion explores what it really takes to lead responsibly in the era of AI. Key Topics Covered: Agents aren't magic, you must observe them. Why oversight is essential as AI agents act and learn autonomously. From black box to glass box. Transparency, explainability, and compliance as non-negotiable design principles. Responsible AI in practice. What observability really means for governance, risk, and trust. The rise of new roles. Why "AI Observer" and "Observability Lead" may soon become critical titles inside legal and business ops. The human dimension. How leaders can apply observability to people spotting stress, isolation, and burnout before it's too late. From pilot to practice. PwC's approach to scaling agentic AI safely through iteration, measurement, and feedback. 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ Never eat alone!  

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 you're in legal, tech, ops, or just wondering what your job looks like in 24 months, this is the episode. Key Topics Covered: The AI Wake-Up Call: Why "change resistance" in legal is dead and what's replacing it The End of Legal Busywork: How AI is freeing up law firms for high-value thinking Billable Hour vs. Business Model: The quiet collapse of traditional legal pricing Speed to Insight: Why fast isn't fast enough anymore and how top teams are adapting Dark Data, Bright Future: New AI tools surfacing value where no one was looking Career Acceleration: Why critical thinkers, puzzle-solvers, and AI-curious pros are thriving The AI-Ready Org Chart: What the "firm of the future" looks like (hint: it's flatter and faster) 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ Never eat alone!

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. And these leaders are already in it. Key Topics Covered: The AI Dividend: What it is, how to measure it, and why it's your next performance metric Data as Infrastructure: Why CLOs are racing to eliminate the "search function" and build a legal "brain" OKRs That Matter: How top legal departments align KPIs to business growth, not compliance checklists Tech Stack in Action: Inside the tools (Copilot, GenAI) that are driving real productivity gains today Talent Evolution: What CLOs actually look for in 2025, critical thinking, adaptability, and strategic fluency Cross-Functional Power Moves: Why your next big win requires partnering with your CIO (or CEO) From Perfection to Performance: Why "excellence over perfection" is the new rule of law 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ Never eat alone!  

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 communication), Shannon talks shop about what it really takes to lead through change in today's legal tech landscape. If you manage teams, advise on tools, or just want to sharpen your edge, this one's for you. Key Topics Covered: Why Shannon trains his team to be consultants, not just executors ChatGPT, Claude, Copilot, Harvey, when to use what, and why Why there's no one AI winner (yet) and what due diligence really means From curiosity to clarity: why communication is the real AI skill How GenAI shifts the legal conversation and why workflows must follow Why legal tech leadership today means being agile, patient, and connected Shannon's weekend writing practice and why he's documenting GenAI's foundation for legal This Episode is presented by Steno: Smarter transcripts. Faster delivery. Built for modern legal teams. 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ Never eat alone!  

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 for privacy law, a sharp eye on emerging tech, and a dose of courage put her on a path that most associates only dream about. If you're a legal professional curious about GenAI, career growth, or making bold moves, this is your playbook. Key Topics Covered: How Melissa leveraged her privacy expertise to break into legal innovation What it really means to "operationalize" GenAI at a top-tier law firm The importance of doing it scared and why courage pays off How Cleary's acquisition of an AI startup created unexpected opportunities Why younger associates might have an edge in emerging tech law The value of curiosity, initiative, and asking the right question at the right moment This Episode is presented by Steno: Smarter transcripts. Faster delivery. Built for modern legal teams. 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ Never eat alone!  

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 to legacy-building with AI-generated video, Stephen shares how he's redefining productivity, growth, and human connection at work and at home. If you're feeling overwhelmed by the noise, or wondering how to lead through change, this one will hit home. Key Topics Covered: Why "value" in legal tech is being redefined and what to do about it How Sullivan & Cromwell vets new tools, partners, and AI workflows The rise of augmented intelligence and how Dooley uses ChatGPT to think, plan, and lead Why creativity, not code, is the real differentiator in this AI moment What founders, vendors, and buyers must understand about trust and timing Lessons from Andrew Sieja, Omar Haroun, and other tech visionaries shaping the next phase How to "come together" in a fragmented market and why small pods of connection matter A personal look into Stephen's use of AI for family legacy and memorialization This Episode is presented by Steno: Smarter transcripts. Faster delivery. Built for modern legal teams. 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ Never eat alone!  

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 relationships made 20 years ago still shape his career today. If you're navigating what's next or building your place in this industry, Phil's story is a masterclass in going far together. Key Topics Covered: What GenAI means now and how it echoes the early days of legal tech How Knowledge Management, strategy, and innovation emerged from organized chaos The power of connection: how one lunch sparked a 20-year peer network Why today's best opportunities aren't in job descriptions, you create them "Follow the joy": Phil's framework for building a career worth having How courage and curiosity created the career he didn't know he was building The future of legal tech leadership and why thinking like a managing partner matters This Episode is presented by Steno: Smarter transcripts. Faster delivery. Built for modern legal teams. 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ Never eat alone!  

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 being shaped by clean data, clear governance, and creative thinking. This episode is packed with real use cases, sharp insights, and powerful takeaways for anyone working at the intersection of law, data, and strategy. Key Topics Covered: What "client intelligence" really means and why it's a growth engine Why governance is the backbone of safe, scalable GenAI The difference between data warehouses, lakes, and lakehouses (finally explained) How cross-functional teams are reshaping client relationships Rachel's ChatGPT workflows - summarizing, strategizing, even grocery shopping AI as a leadership tool: how to support your team and stay ahead Inclusion, accessibility, and the future of data-driven collaboration This Episode is presented by Steno: Smarter transcripts. Faster delivery. Built for modern legal teams. 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ Never eat alone!  

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. We dive into how teams are building confidence, collaboration, and creativity through tools like Copilot, Grammarly, and ChatGPT, along with what it means to work across silos, connect with communications teams, and lead from a place of openness and curiosity. Key Topics Covered: How GenAI tools like Copilot, Grammarly, and ChatGPT are leveling the playing field Supporting neurodiverse professionals through AI-enabled workflows Building psychological safety and confidence across technical teams Working across silos: IT + Communications = new power partnerships Why accessibility and inclusion need to be built into tech strategy What's changing at ILTACON and why it feels different this year From recipes to real strategy: how personal AI use is driving workplace adoption This Episode is presented by Steno: Smarter transcripts. Faster delivery. Built for modern legal teams 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ Never eat alone!  

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 strategic leaders. From workflow automation to workforce evolution, Julie breaks down what's changing, what's coming next, and how to stay ahead in a profession that's reinventing itself in real time. Key Topics Covered: How GenAI has flipped the script on legal tech adoption Why attorneys are now driving the demand for innovation The shift from eDiscovery silos to full-firm strategic impact What the rise of digital agents means for tomorrow's workforce How legal ops teams are becoming drivers of business value Julie's "second career" in agent design, automation, and workflow strategy Why human-in-the-loop AI still matters and always will   This Episode is presented by Steno: Smarter transcripts. Faster delivery. Built for modern legal teams. 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ Never eat alone!

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 You'll Learn: Why one bad GenAI ruling could halt progress for 10 years How "hallucinated" case law is already damaging court credibility The question no one can agree on: Are AI prompts discoverable? What smart firms are doing right now to stay defensible Why your judge's tech IQ might matter more than your case facts The #1 safeguard Judge Peck says you must have in place today What DLA Piper is doing that most law firms still haven't figured out 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ Never eat alone!  

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, overloaded, or looking for a competitive edge - you need to hear this! Key Topics Covered: The AI tools shaking up court reporting (Transcript Genius, Verbit AI, and more) The security blind spot in transcript workflows and how to close it Why "context engineering" is your next competitive advantage Agentic workflows explained: what they are and why they matter The myth of the disappearing billable hour and what's actually happening How Stephanie builds AI muscle on weekends (and why you should too) Field-tested career advice for rising legal ops pros   This Episode is presented by Steno: Smarter transcripts. Faster delivery. Built for modern legal teams. 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ Never eat alone!