Careers and the Business of Law

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!    

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, it’s about scaling their judgment. If you're serious about where your team, talent, and tech are headed, this is the episode. Key Topics Covered: What law firms and legal departments can learn from Palantir’s forward deployed model Why context, not prompts is the real power source behind GenAI in legal workflows The new business value of outside counsel: from selling information to selling judgment How tools like DraftWise unlock contract data and turn junior lawyers into high performers fast The evolution of roles in legal: from lawyers to context engineers, data strategists, and AI copilots Augmented intelligence > artificial intelligence: the case for keeping humans in the loop What legal AI tells us about the next wave in the demand and flow of talent People & Ideas We Mentioned: Alex Karp, CEO of Palantir – the philosopher-CEO shaping how the world thinks about data and power Kyle Bahr from Cleary Gottlieb – sparking smart conversations on context engineering and where legal AI is headed Omar Haroun, founder of Eudia (formerly Text IQ) – pushing the boundaries on augmented intelligence in legal Song of the Day: “Celebrate” by Jordan Rakei – Will’s go-to morning track – Give it a listen 🎧 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!  

Bestselling author and “non-obvious” thinker Rohit Bhargava sits down with David Cowen for a high-energy, idea-packed conversation on creativity, persuasion, and building influence in unexpected ways. Drawing from his global bestseller and branding roots at Ogilvy and Leo Burnett, Rohit shares how to spot hidden patterns, spark change inside organizations, and bring others along the journey. If you’ve ever felt like the only one seeing around corners, this episode is for you. Key Topics Covered: The 4 habits of non-obvious thinkers (and how to build them daily) Why ideas alone are worthless and what separates dreamers from doers The Einstein lesson: how to find (and be) your “Max Planck” Self-serving altruism: the underrated power move in building influence How to get others to join your vision without a “hard sell” The art of persuasive storytelling from someone trained at Ogilvy and Leo Burnett Why getting outside your echo chamber is the secret weapon for innovation Speacial mention: Rohit’s latest bestseller, Non Obvious Thinking, is now available, don’t miss 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/ Never eat alone!  

Frank Nuzzi, Senior IP Counsel at Siemens, joins David Cowen to unpack the mindset shift every legal professional needs right now. From sandboxing with Microsoft Copilot to pushing the boundaries of AI in legal workflows, this episode dives into how curiosity and experimentation, not perfection are shaping the next generation of legal work. If you're waiting for AI to be flawless before jumping in, you're already behind. Key Topics Covered: Why “don’t be cheap on your career” might be the best AI advice you’ll hear The productivity edge: how Copilot saves time in Outlook and sharpens legal workflows Frank’s system for learning fast: white papers, eBooks, YouTube, and morning study How genAI accelerates legal research and boosts comprehension The reality of “time saved” in legal, quality over quantity Lessons from DHL’s legal playbooks and the power of asking “what if?” Why staying curious is the real ROI of AI tools 🎧 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!

Catherine Jopling, General Counsel at MPW Industrial Services, doesn’t lead from behind a desk, she builds trust in the field, layer by layer. In this episode, she shares how she leads legal with empathy, curiosity, and proactive strategy in a decentralized, blue-collar business. Instead of waiting for crises, Catherine gets ahead of them, visiting sites, meeting people where they are, and building systems that make legal a value driver, not a cost center. Whether she’s coding a risk registry in SharePoint or talking AI with her executive team, she proves that innovation doesn’t require big budgets, just resourcefulness and courage. 🎙 Highlights: Leading a lean team of 7 serving 4,000+ across North America Legal as a proactive partner, not a reactive fixer DIY tech: Building risk tools with ChatGPT + SharePoint Trust as the foundation, human connection > automation Leadership lessons from books, site visits, and Whitney Houston 💡 Takeaways: Build trust before it’s needed Innovate with what you have Legal can and should drive value AI is powerful, but relationships are everything 🎯 Try this: Reconnect with someone in your org before you need to. And take one small step toward building something new, just like Catherine. 🎧 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!  

Live from the DHL Legal Innovation Summit, David Cowen sits down with Omar Haroun, co-founder of Eudia, to break down the shift from artificial intelligence to augmented intelligence. Together they unpack what’s actually happening in legal innovation: smarter workflows, real cost transformation, and human-machine collaboration at scale. This conversation goes deep from M&A disruption with DHL to the messy middle of change, to the opportunities ahead for those willing to live in the future. If you're trying to figure out how to adapt, evolve, and lead with AI at your side, start here. What You’ll Learn: Why AI isn’t replacing lawyers but the ones who use it might The real reason behind layoffs (hint: it’s not just tech, it’s operational innovation) How DHL and Eudia are unbundling legal services and redefining M&A speed What it means to be a Pattern Breaker and why “messy middle” is where the magic happens Don’t wait for the dust to settle. If you're a seeker, striver, or top guard thinking out loud about AI, talent, and transformation, this one's for you. 🎧Subscribe. Share it with a co-conspirator. And if you're not living in the future yet… what's holding you back? 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ Never eat alone!  

What happens when you take legal operations, move it into finance, scale it globally, and build a team of 85 legal professionals inside a Fortune 500? You get Brian Edge’s world and it’s nothing short of groundbreaking. Live from the DHL Legal Innovation Summit, David Cowen sits down with Brian, SVP of Legal Franchise & Integrity Shared Services at MasterCard, for a high-energy, human-centered conversation on the next evolution of legal ops. From creating capacity through shared services to layering AI on top of HI (human intelligence), this episode is about unlocking better work, better relationships, and better outcomes at scale. What You’ll Learn: Why shared services might be the next big leap beyond traditional legal ops How MasterCard scaled legal support globally without outsourcing its soul The surprising power of empathy, data, and dashboards in shaping business outcomes How AI is enabling, not replacing human brilliance in legal service delivery This is legal operations V.3, more collaborative, more strategic, more human. 🎧 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 raw and energizing conversation of Careers and The Business of Law from the DHL Legal Innovation Summit, David Cowen sits down with Matthew Smith, Executive Vice President of Business Developmentat Array, to talk about building trust, managing high-performing teams, making the leap into legal from healthcare, and navigating the “middle of the middle” of a career. From the fear of hearing no to the power of shutting up and listening, this is required listening for anyone climbing the jungle gym of leadership. What You’ll Learn: How great leaders coach, not micromanage Why listening is the most powerful (and overlooked) sales move What it really means to lead in the “middle of the middle” How values, vision, and relationships shape the second half of a career Like what you hear? 🎧 Subscribe. Share. Send to someone who needs a jolt of clarity. Because your career’s not a ladder, it’s a jungle gym. And the climb gets better when we do it together. 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ Never eat alone!  

Live from the DHL Legal Innovation Summit in Columbus, David Cowen sits down with Christina Wojcik, Head of Innovation & Partnerships at Pearson Ferdinand, for a high-energy conversation on the future of legal services. Christina breaks down what it means to build a truly tech-first law firm, no associates, no legacy systems, just streamlined, partner-led innovation. From back-office automation to smarter pricing models, this episode explores how law firms can operate leaner, move faster, and deliver more value in a rapidly evolving market. Key Takeaways: Tech-first law firms are rethinking structure, no associates, just distributed, empowered partners Automating admin tasks frees up time, margin, and talent for high-value client work Clients want to partner on innovation, not just hear about it We’re in the messy middle of transformation, and the opportunity is wide open 🎧 Tune in, share with your team, and subscribe for more conversations that move legal from now to next. Because careers aren’t ladders, they’re jungle gyms. 💡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: The Legal Data Intelligence Series, David Cowen sits down with Richard Pachella, Strategic Alliance Advisor at Epiq, to unpack the seismic shifts happening across legal tech, operations, and talent. If you're in eDiscovery, legal operations, or just trying to navigate your career in the age of AI, this episode is for you. 🔥 What you’ll hear: Why the smartest legal pros are leaning into AI now, not later How the lines between litigation support, M&A, regulatory, and compliance are blurring fast What today’s legal departments need: prompt engineers, strategic consultants, and legal technologists who think beyond the silo How LDI is transforming from a “think tank” to a “build tank” Practical ways to adopt GenAI tools in your day-to-day, starting today 📣 Plus: Rich drops a 60-second insider take on what Epiq is hiring for, and why diverse backgrounds are more valuable than ever. 🎧 If you’re serious about staying relevant, expanding your skills, and thinking out loud with the best in the business, press play! 💡To learn more about the future of legal innovation, visit https://cowengroup.com/ Never eat alone!