Careers and the Business of Law

Live from Legalweek 2026, David Cowen sits down with Rian Kennedy, Director of Legal Hold Sales at DISCO, to talk about what has actually changed in legal tech over the last 12 months. The conversation goes beyond AI hype and gets into what matters now: cloud maturity, agentic workflows, insourcing pressure, tighter budgets, and why legal teams are starting to use technology to control spend, consolidate systems, and rethink where legal ops ends and business ops begins. Hosted by David Cowen Key Topics Covered Why the legal market has moved from cautious curiosity to real AI adoption, with law finally pushing to stay competitive instead of lagging behind How the pandemic accelerated cloud adoption and set the stage for today's faster embrace of GenAI and agentic AI Why the most valuable buyers are still the innovators who want to build alongside vendors before tools become table stakes How corporate legal teams are reassessing what to keep in-house, what to send to outside counsel, and where ALSPs fit in the middle Why legal ops leaders who mastered contracts and workflow discipline are now asking the bigger question: what comes next How litigation budgets are becoming a strategic focus, with more interest in visibility, control, consolidation, and reducing outside counsel spend Why legal hold, eDiscovery, and preservation are becoming more important as data sources multiply and automation becomes essential

Live from Legalweek 2026, David Cowen sits down with Rhys Hodkinson, CRO of Definely, to explore where legal AI gets truly useful for transactional lawyers. This episode is about moving beyond generic speed gains and into something more valuable: systems that understand contracts, surface the right context at the right moment, and help lawyers think more strategically without sacrificing precision or professional judgment. Hosted by David Cowen Key Topics Covered Why Definely was built to solve a problem most legal tech ignored: helping transactional lawyers work inside long, complex contracts where context is everything How Definely surfaces definitions, cross-references, schedules, annexes, and related documents directly inside Microsoft Word Why the real moat in legal AI is not just the model, but the grounding layer that understands how contracts actually work How prior contracts, past definitions, and historical drafting patterns can turn AI from a generic tool into a true drafting ally Why firms are under pressure to move faster with AI while still carrying the same professional liability for the final output Rhys's view that the market still has not figured out what to do with the AI dividend, even as lawyers gain speed, capability, and better output Why the next legal tech battle may be about interface and control: who becomes the layer where lawyers actually work, while specialized tools plug in behind the scenes

Live from Legalweek 2026, David Cowen sits down with Alex Smyth, EVP and General Counsel at LexisNexis, to talk about where legal AI is finally getting real. The industry is moving past one-off experiments and into repeatable workflows that cut turnaround times, reduce manual work, and deliver answers lawyers can actually trust. The big question now is no longer whether to use AI. It's how to embed it into legal work in a way that is authoritative, scalable, and measurable. Hosted by David Cowen Key Topics Covered Why the legal market is shifting from AI experimentation to repeatable workflows that automate entire sequences of work How LexisNexis built an NDA workflow that reviews, comments, escalates when needed, drafts the response email, and cuts review time from days to minutes A measurable legal ops outcome: LexisNexis reduced contract turnaround time in tracked segments by 22.7% over the last year Why nearly 300 legal workflows matter more than generic prompting, especially when lawyers need structured, repeatable outcomes The difference between general-purpose AI and purpose-built legal AI grounded in authoritative, curated legal content Why authoritative content still matters: lawyers need current law, validated citations, and trusted outputs, not just plausible answers Alex's view that the market is at an inflection point, where the real return on AI will come from embedding workflows directly into legal process

Live from Legalweek 2026, David Cowen sits down with Dennis Garcia, Vice President and General Counsel of Litera, to unpack what legal leaders still get wrong about AI, networking, and business impact. This episode is really about leverage: how trust, responsiveness, relationship-building, and smarter risk-taking turn legal from a support function into a revenue driver. Hosted by David Cowen Key Topics Covered: Why your network is still your net worth, and why LinkedIn remains one of the most underused career assets in law How commenting consistently on LinkedIn can build visibility, credibility, and real-world opportunities over time What Dennis learned moving from Microsoft to Litera, and why earning trust starts with responsiveness and clarity Why legal departments should stop being the department of no and start becoming business enablers How faster contract cycles drive revenue, margin, and growth by shrinking time to deal Why smaller legal teams need to be scrappy, versatile, and fluent in legal ops, AI, and business priorities The real future of legal work: combining human intelligence and AI to build trust, close deals, and move the business forward

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 is: which legal professionals will adapt in time? What you'll learn: Why the litigation AI market has officially matured - and who's winning How Syllo was built by a litigator for litigators, not as a generic platform Why the old step-by-step workflow is dead - and what's replacing it What associates are really feeling right now, and what they need to hear Why 2025–2026 may be the most career-defining window in modern legal history

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 by David Cowen Key Topics Covered Why people, process, and technology - in that order - determine whether legal AI actually delivers results The Ford assembly line analogy for law: how breaking legal work into workflows unlocks massive efficiency gains Why buying AI tools without redesigning the operating model almost always fails The rise of AI agents as "digital teammates" that extract clauses, analyze risk, and automate contract review How one global company is redesigning its legal function to cut 12,000 contracts down to 5,000 through standardization The hidden enterprise opportunity: poor contract management may cost companies up to 11% of revenue each year Why the lawyer of the future becomes the conductor of an AI orchestra rather than the person playing every instrument

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 teams, and why the "last mile" is the battleground that matters now.  Hosted by David Cowen Key Topics Covered: Why AI output that can't be verified fast is worse than useless, and how verification time kills ROI The "last mile" framework: where legal workflows break down and why most tools stop too early How Clearbrief was built around mistake-catching before GenAI and why that design choice aged perfectly What customer discovery really looks like (200+ lawyer interviews, brutal feedback included) The shift toward insourcing: which litigation and investigation tasks stay in-house and which never will Why general-purpose chatbots help with drafting, but fail at delivery, defensibility, and trust A practical metaphor for AI adoption speed: the engine is fast, the road isn't, and lawyers are the drivers

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 heading, where talent demand is exploding, and how to future-proof a legal career without chasing hype. Key Topics Covered Why email, Slack, and Teams are no longer enough to satisfy regulators and what replaces them The regulatory shift driving mobile collection at unprecedented scale (from 12 phones to 10,000+) The hidden "tax" of smartphone non-compliance, including billions in fines and stranded hardware How remote, scoped mobile collection reduces privacy risk while increasing defensibility Where talent demand is surging most: corporate legal, legal ops, and forensic hybrid roles How to use the "12% AI dividend" to pivot into high-growth forensic and compliance work A practical weekend playbook for upskilling: case law, OS changes, and encryption updates Special Shoutout:  Scott Milner – Recognized for bridging deep technical expertise with practical leadership in eDiscovery and regulatory strategy Greg Mazares – ModeOne board member and trusted mentor, shaping how technology is applied to real client problems Jerry Bui (Purpose) – Cited for his perspective on the growing importance of forensics in modern legal workflows Nathaniel Whittemore – Host of The AI Daily Brief, referenced for framing the MIT insight on task-level automation Joseph Pochron – Nardello, recommended as a future guest for his visibility into corporate investigations and compliance Anthony Cardine  – O'Melveny & Myers, highlighted for his leadership at the intersection of eDiscovery, paralegal teams, and operational change

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

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.

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

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.

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.

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.

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.

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.

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.

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)

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

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.

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.

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.

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.

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.

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

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.

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

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.

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

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. 

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

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.

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.

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.

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?

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

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.

20 Years. 5 Pivots. 1 Big Bet on GenAI.

Let's get something straight: the job of General Counsel has left the building. Today's GCs aren't just legal advisors, they're business architects, transformation leaders, and culture drivers. And if your legal team is still playing defense, you're losing ground. In this episode, Lisa Mather and Tim Fraser, two of the most forward-leaning legal execs in the game, pull back the curtain on how they're redefining the GC role from the center of the business. What you'll walk away with: Why Legal Ops is outgrowing its old box and becoming strategic leadership. How the best GCs are operating at “120%” by speaking the language of margin, growth, and product. The mindset shift from “risk management” to “value creation” and what that means for your next hire.

In this no-BS roundtable, David Cowen sits down with Kevin Cohn - Chief Customer Officer at Brightflag; Tyler Finn, Head of Community & Growth at SpotDraft; and Matthew Wheatley, VP, Client Strategy at Priori to unpack the real state of legal operations, talent, and transformation. Forget the panel buzzwords. This episode pulls back the curtain on what's actually happening inside high-performing legal teams. What's inside: • Legal ops has hit a plateau, but careers haven't. The smartest players are skipping the next rung and stepping into legal strategy, transformation, and C-suite alignment. • There's no ladder, just a jungle gym. From executive assistants to legal COOs, this episode is a playbook for navigating ambiguity and turning it into an advantage. • The real skill gap? It's not tech. It's knowing your value. Are you a builder, a manager, or a creator? Know your lane, then double down. This is the episode you forward to your team with one line: “This is the conversation legal ops needs to hear right now.”                                                           

Headed to CLOC? So are E.J. Bastien and David Cowen and this episode is your field guide. Before you start speed-walking the ARIA hallways and hunting for coffee and co-pilots, listen in. E.J. Bastien has spent two decades at Microsoft reimagining what in-house eDiscovery and litigation support can be. He's leading teams, building AI agents, and solving tomorrow's problems with tools that most legal teams haven't even touched yet. In this pre-CLOC masterclass, we dig into: How Microsoft is using GenAI to streamline review, code documents, and surface case-critical facts before a human ever sees them What it really means to build a bespoke agent trained on your legal team's workflows not ChatGPT, but your playbook Why perfectionists are out, and “learn-it-alls” are in and how that mindset shift is the secret to surviving (and thriving) in 2025. You'll also hear what it takes to lead with confidence, experiment without fear, and stay grounded in the face of constant change. It's Vegas. It's CLOC. It's time to stop chasing answers and start trading playbooks.

Guest: Kevin Cohn, Chief Customer Officer, Brightflag Host: David Cowen, President, The Cowen Group

What happens when a GC thinks like a CEO, rolls up his sleeves like a contractor, and leads like a startup founder? You get Mark Smolik, Chief Legal Officer of DHL Supply Chain, and a masterclass in legal leadership you can't afford to miss. This episode is a front-row seat to how Mark turned blue-collar grit, data discipline, and a sharp eye for ROI into a legal department that runs like a high-performance business unit. We unpack: His $37,000-a-claim insight that reshaped risk management. A bold AI deployment that eliminates human review in M&A due diligence. And the why behind DHL's Legal Innovation Summit, June 3–4 in Columbus, where his full team will share the playbook. If you're wondering how to go from ideas to impact or how to just start, this is the episode. One of the best conversations we've had.

We're not in Kansas anymore. We're in the Jetsons Era. Legal Data Intelligence isn't just tech, it's talent, timing, and the ability to see around corners. In this episode, I sat down with Stacy Lettie, Chief of Staff to the General Counsel at Organon, and we went from Disney to data to dogs with AI collars. Yes, really. We talked: Why the future of legal starts with foundations (Small World → Tron) What makes a great Chief of Staff When imposter syndrome disappears (spoiler: when you earn it) And the moment we decided—live, in-person—to build AI agents at Microsoft this July

This one hits different. David Cowen sits down with legal operations leader Carl Morrison (Otsuka Pharmaceuticals) for a sharp, high-energy conversation on how legal teams are turning data into strategy, and why now is the moment to clean house, ditch the ROT (redundant, obsolete, trivial), and drive real value. Yes, we open with Lady Gaga, because transformation has a rhythm. But what follows is a masterclass in Legal Data Intelligence (LDI) and the future of legal operations. In this episode: Why your data is a goldmine, but only if you mine it right How AI is changing early case assessment and risk visibility What LDI really means, and why it's not just about cost control anymore How legal ops teams are becoming strategic drivers, not just back-office fixers Carl also shares what it means to move from dirty data to strategic sun, and how to build a cleaner, smarter, faster-functioning legal department in the age of AI and collaboration. Whether you're in legal ops, litigation, InfoGov, or leading a law department, this is your blueprint for going from now to next!

“Life is a carnival—and legal ops is leading the parade.” What happens when strategy, storytelling, and AI collide in the hands of a legal operations leader? You get this high-energy, insight-rich episode with Elizabeth Lugones, VP of Professional Services at Mitratech, a legal tech pro who's been writing and speaking about workforce automation since before it was cool. What You'll Hear: Why change management is really just executive storytelling How Sarah Sawvell at Honeywell, along with Mitratech and Morae, is crushing implementation through collaboration The shift from “cut costs” to “see around corners” in legal value How Liz and David use AI agents like ChatGPT + Gemini to create time dividends in real life Shoutouts to innovators like Stephanie Corey, Stacey Lettie, Anna Richards, Brittany Leonard, and more If you're leading transformation or trying to ride the wave, it's time to rethink what legal value really means. Elizabeth brings the clarity. David brings the energy. And the future of legal just might be more human than ever.

What happens when three top legal innovators challenge everything we know about leadership, AI, and the future of law firms? In this high-energy episode of Careers in the Business of Law, David Cowen sits down with three powerhouse legal minds who are redefining innovation, knowledge management, and practice transformation at major law firms. But here's the twist—we're not telling you who's who right away! Topics That Will Change How You Think About Legal Leadership: Who's really driving innovation - clients or law firms? Why curiosity is more valuable than having all the answers. How AI is transforming legal work - but only if you ask the right questions. What top law firms are doing to stay ahead of the disruption curve. The "hidden ROI" of legal innovation (hint: it's not just about saving time). Connect with Our Experts & Learn More: - Ilona Logvinova – Director of Practice Innovation at Cleary Gottlieb - Esther Bowers – Chief Practice Innovation Officer at Honigman LLP - Evan Shenkman – Chief Knowledge & Innovation Officer at Fisher Phillips

Legal data isn't just for eDiscovery anymore—it's a strategic weapon. AI-driven analytics are transforming legal teams into business intelligence powerhouses, helping HR, compliance, and cybersecurity teams solve problems faster than ever before. In this episode, Benjamin Sexton (JND) shares: How AI is shifting legal work—are we saving time or just creating more high-value tasks?  Why legal teams are becoming the “calculators” of business intelligence How Walgreens and other companies use eDiscovery tools to solve compliance challenges in hours, not weeks  If you're in eDiscovery, legal ops, or compliance, this episode will change how you think about legal data—and your career. 

The legal industry is facing its “Netflix vs. Blockbuster” moment. AI, automation, and alternative legal service providers (ALSPs) are rapidly reshaping how legal services are delivered, and the biggest question is: Who will adapt—and who will be left behind? Roger Pilc leads a $600M+ division at Epiq, bringing experience from McKinsey, Booz Allen, CA Technologies, and Pitney Bowes. With insights from Satya Nadella's vision on AI, Clayton Christensen's The Innovator's Dilemma, and leadership lessons from Peter Drucker, Adam Grant(Author of Think Again), and Daniel Pink(Author of Drive), Roger explains how ALSPs are positioned to disrupt legal in ways law firms and Big Four consultancies cannot. In this episode, we explore how Legal Service Management mirrors IT's digital transformation, why Zach Posner at TLTF is betting on AI-driven legal platforms, and how Nicole Giantonio and the team at Epiq are investing in tech that's changing legal service delivery. Key Takeaways You Can Use Today: Legal is facing a “Simultaneous Equation Problem.” GCs must manage rising litigation, regulatory complexity, and shrinking budgets—but traditional models no longer work. AI & ALSPs Are Changing Everything. Like Netflix disrupting Blockbuster, AI-powered legal service models are creating massive efficiencies for corporate legal teams. The 30% Rule: Leadership is Talent Spotting. Echoing Bill Gates, Steve Jobs, and Jack Welch, Roger spends 30% of his time recruiting and developing top talent—a critical strategy for legal leaders.

Ever wonder how to build a career worthy of a Lifetime Achievement Award? My latest guest, Jay Leib, has done exactly that—and he's here to share how. From his early days in software sales at RTI, to leadership roles at EY, Relativity, NextLP, and now Reveal, Jay has built his career through radical curiosity, relentless networking, and entrepreneurial grit. We cover Jay's jungle gym-like career moves, why curiosity and communication matter more than certifications, and the hacks that helped him create lasting connections—from LinkedIn coffee meetings to mentorship lessons from VC icon Troy Henikoff.