Careers and the Business of Law

Hosted by David Cowen | Careers and the Business of Law David Cowen sits down with Bobby Malhotra, litigation partner and chair of Winston's eDiscovery and Information Governance practice, member of the firm's AI strategy group, and founding member of Legal Data Intelligence. Bobby sits at the intersection of eDiscovery, digital forensics, cross-border data, privacy, cybersecurity, information governance, and AI governance, bringing a rare combination of legal judgment, technical fluency, and hands-on curiosity. This conversation covers why AI governance has arrived, why information governance is making a comeback, and why the next generation of legal professionals will need to become tech-and-data lawyers. WHY THIS MATTERS? AI governance is no longer a future issue. It is already here. Companies are dealing with employee use of public AI tools, data exposure, privacy risk, cybersecurity concerns, regulatory pressure, AI policies, privilege questions, AI transcription, and AI-related incidents. For lawyers and legal professionals, this is one of the clearest career white spaces in the market. KEY TAKEAWAYS AI governance has arrived. It is already one of the hottest and busiest areas in the legal industry. AI governance is about vision, guardrails, policies, ethical obligations, legal obligations, regulatory compliance, and business risk. Information governance is the backbone of AI governance. You cannot govern AI if you do not know where your data lives. Data governance sits inside AI governance, and may be the most important part of the whole program. The legal role is expanding, not shrinking. AI governance and data governance are creating new career lanes across law firms, corporate legal departments, privacy, cybersecurity, eDiscovery, and legal operations. You do not need 20 years of AI governance experience. No one really has that. Curiosity, teachability, issue-spotting, and legal judgment matter more. The best professionals in this space combine legal thinking with technical literacy. It is not just about knowing the tools. It is about applying the law to the facts, the technology, and the risk. AI governance is not just about models anymore. It now includes privilege protection, AI transcription, employee AI usage, public AI tools, data exposure, and AI-related breach scenarios. Outside counsel and in-house teams both have a role. Some companies rely heavily on outside counsel, while others use outside counsel for strategy, policy review, sanity checks, regulatory guidance, and high-risk questions. If you want to build a career in this space, get comfortable being uncomfortable. Follow the law. Follow the technology. Find mentors. Set up news alerts. Stay close to communities like LDI and IAPP. PEOPLE

Hosted by David Cowen | Careers and the Business of Law David Cowen sits down with Mark Allen, Director of Legal Operations and Strategy at Zillow Group - a title that is itself a signal of where the legal ops function is heading. Before Zillow, Mark ran legal operations at Netflix and Activision Blizzard, and has sat on the vendor side at Brightflag and CloudCourt. He's also a newly seated CLOC board member. This conversation covers career advocacy, the vendor-buyer relationship, and why legal ops is quietly becoming one of the best business training grounds in any industry. WHY THIS MATTERS? Legal operations is no longer just a support function - it's becoming the operating engine of the modern legal department. If you're in legal ops today and not thinking about AI, business strategy, and executive influence, this episode is your roadmap. KEY TAKEAWAYS Titles follow impact, not the other way around. Show the work first, then have the conversation. Legal ops is the COO role for a legal department - tech, finance, project management, people, and strategy all in one. Be clear about your intentions with your manager. Doing the work silently is not enough - say it once, clearly. If your leader never sees your value after repeated attempts, it's time to move on. Know your worth. Introverts may actually have an edge - action speaks louder than talk tracks. Vendors: skip the 30-minute sales deck. Show the tool. Buyers know what they need within 15 minutes. Make friends with vendors even when you're not buying. It's a knowledge exchange, not just a sales call. Finance and HR are your fastest path to the executive table internally. Legal ops professionals are being asked to change an operating model that has existed for hundreds of years. An AI-first mindset is no longer optional. Legal ops is essentially a small business degree - creativity, risk-taking, and cross-functional thinking built in. PEOPLE MENTIONED David Cowen — Host Mark Allen — Director of Legal Operations and Strategy, Zillow Group; CLOC Board Member Jen McCarron — Former President of CLOC; Netflix colleague of Mark's Mary O'Carroll — Legal ops trailblazer Jason Barnwell — Legal ops trailblazer Rajan Gupta, Ryan Black, Leo Murgel, Stacey Lettie - Legal ops market leaders referenced Olivia Dean — Artist; Mark's exit song pick ("Nice to Each Other") COMPANIES CLOC Core 12 referenced; CLOC.org <li

Hosted by David Cowen | Careers and the Business of Law Fresh off four days at McCormick Place in Chicago, David Cowen sits down with Oyango Snell, President co-author of the State of the Industry Report <a href= "https://www.linkedin.com/in

Hosted by David Cowen | Careers and the Business of Law Adam Rouse (Walgreens), Ashley Christakis (CrowdStrike), John Koss (Mintz), and Major Baisden (Lineal) pick up where they left off at LegalWeek in New York - ten weeks later, the conversation is sharper. The question on the table: how do you evaluate legal technology when the problem isn't fully defined yet? The answer involves a framework, a maturity arc, and a lot of grace. WHY THIS MATTERS? If your legal team is still waiting for the perfect data environment before acting on AI, you're already behind. This group agrees: the chaos is the condition. The only way through it is a deliberate strategy, documented workflows, and the courage to take the first step. KEY TAKEAWAYS Comfort with the unknown is the new baseline. The velocity of AI adoption has accelerated the FOMO - but the core evaluation process hasn't changed as much as we think. The three I's - Initiate, Investigate, Implement - apply to more than technology. Use them for concepts, use cases, and people, too. Most legal departments are somewhere between ad hoc and operational on the maturity arc. Very few are close to optimized - and that's okay. Stop chasing use cases. Start documenting how you actually get work done. That's the unlock for AI value. Data nirvana doesn't exist. Progression and discipline do. Don't wait for a perfect data ecosystem before extracting value. AI is the great information governance equalizer. Nothing is obscure anymore - if it's accessible, it will get indexed. The real AI dividend isn't just productivity. It's capability - doing things you were never able to do before. Know why you're doing what you're doing - and why you're not doing what you're not doing. That clarity builds organizational confidence and stronger client relationships. PEOPLE MENTIONED David Cowen - Host Adam Rouse - Sr. Counsel, eDiscovery & Director Legal Operations, Walgreens Ashley Christakis - Former Senior Manager, Legal Data Intelligence, CrowdStrike John Koss - Head of Innovation, AI, and E-Data Consulting, Mintz Major Baisden - CEO, Lineal Services COMPANIES MENTIONED Walgreens - Large enterprise legal operations navigating AI adoption CrowdStrike - Corporate legal team investing in technical curiosity and R&D thinking Mintz - Law firm with a formalized data strategy committee and Director of Data Strategy Lineal - Legal services company using AI to record, document, and optimize workflo

Hosted by David Cowen | Careers and the Business of Law Everyone's talking about Harvey, Legora, Spellbook, and Ivo. Nobody's talking about what they ride on top of. Tom Baldwin - founder and CEO of Entegrata, former CIO at Foley, Sheppard Mullin, Reed Smith, and Cadwalader - argues the real story is data infrastructure. Without a single source of truth, every AI tool in your firm is working from a partial picture. WHY THIS MATTERS? If your firm is buying AI tools without auditing the data underneath them, this is your warning shot. Tom's framing: toaster ovens need an electrical grid. KEY TAKEAWAYS AI tools work on narrow tasks, not whole-firm intelligence. 50 asset purchase agreements? Great. 200 million documents? No. Pulling documents out of your DMS strips away the metadata that makes them valuable - judge, opposing counsel, area of law, industry. That context is what AI actually needs. Business-of-law use cases (lateral prediction, cross-sell, client attrition, FP Azure/Databricks/Fabric are the modern stacks.  Cost is roughly the same at 200 lawyers or 2,000 - six figures, ongoing. Compute and storage are cheap; talent is the investment. Firms move from "nice to have" to "must have" after a near-miss. Tom's example: a firm almost fired an associate because their FTE calc didn't account for maternity leave. The chief data officer is becoming a real C-suite role. Sidley's among the early movers. Watch the forward-deployed legal engineer trend. Harvey is hiring practitioners for these roles. PEOPLE MENTIONED David Cowen - Host Tom Baldwin - Entegrata founder Entegrata's first angel investor Renee Morris, Katrina Dittmer, Glenn LaForce - Data leaders Tom mentioned COMPANIES AND TOOLS MENTIONED Entegrata - Turnkey data lakehouse in Azure Snowflake, Azure, Databricks, Microsoft Fabric - Data platform stacks Harvey, Legora, Spellbook, Ivo - Practice-of-law AI tools Sidley Austin - Early adopter of the chief data officer role 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this ep

LexisNexis CEO of Global Legal Sean Fitzpatrick joins David Cowen to unpack the newly announced strategic alliance with Luminance and what it signals about where legal work is actually headed. From the "trust-first" shift replacing better-faster-cheaper, to law firms growing margins while raising rates, to the emergence of an entirely new role (manager of agents), this conversation is a candid read on how AI is reshaping the practice, the workflow, and the talent equation in legal. Key Topics Covered Why the LexisNexis and Luminance integration was customer-demanded, and how authoritative legal content plus contract intelligence changes the workflow equation ChatGPT as a step change, not an incremental shift: the strategy stayed the same, the tools changed everything The three buckets of legal work (repeatable/rules-based, judgment-based, and pure thought leadership) and where AI actually plays The "AI dividend" in practice: a GC reclaiming 10 hours a week to turn warranty claims from cost center into profit driver Why trust now outranks speed and cost as the dominant buying criterion in legal AI How law firms are growing revenue faster than cost base, and pushing high-single-digit rate increases The role that doesn't exist yet: manager of agents, leading a workforce with no human employees "AI fluidity" as the new hiring filter, plus career advice on reputation, partner selection, and taking risks early (with a Shoe Dog recommendation) 🎧 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://solid.legal/podcasts/ Never eat alone!

Kim Wolfe is one of the few non-lawyer executives running operations at the top of corporate legal. With a Wharton MBA and a quantitative background, she leads legal administration at State Street. David Cowen sits down with Kim to unpack what executive-level legal ops looks like inside one of the world's most regulated industries, and the career advice that changed everything. Key Topics Covered: The non-lawyer operator archetype: How business operators in legal leadership are reshaping the function Banking's slower AI path: Why regulation means Kim is two steps behind Intel and HP, and okay with that Lawyer-to-lawyer training: Why pairing power users with hesitant adopters moves the needle Who owns training: Why 67 percent of legal ops says it belongs to them The career lesson: As long as I see you here, I cannot give you more The 5:30 AM discipline: Why two hours of solo thinking is Kim's most important investment Simulation training: Why flight-simulator-style learning may fix inconsistent mentorship 🎧 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://solid.legal/podcasts/ Never eat alone!

Mary Agbovi runs legal operations at CoverMyMeds, sits on the SOLID Advisory Council, and co-founded an organization that builds schools in Togo. David Cowen sits down with Mary to unpack the most quotable metaphor in the entire series: what if we had given Alexander Hamilton a typewriter? It is a reframing of change management that strips away the fear of AI replacement and replaces it with something more useful, we are handing our teams tools to be more of who they already are. Key Topics Covered: The Hamilton typewriter metaphor: Why we are giving people an amplifier, not asking them to change identity Concentric circles of AI rollout: Mary's framework for thinking about adoption — direct team first, then the surrounding stakeholders The bell curve of adoption: What to do with the leading 20 percent, the middle 60, and the trailing edge Building schools, building legal ops: Why creating space for people to learn is the same fundamental work Inspiring agency: Why storytelling is the differentiator for legal ops leaders in 2026 Articulation as AI dividend: How Mary uses AI as a coach to refine her own thinking Project managing a life: Three daughters, building schools, leading legal ops 🎧 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://solid.legal/podcasts/ Never eat alone!

Carl Morrison is the legal operations ambassador to Las Vegas, a CLOC board member, and one of the people who built the legal operations function on the Las Vegas Strip. David Cowen sits down with Carl to trace the evolution of legal ops from his first CLOC at the Bellagio a decade ago to today's McCormick Place, and to unpack the central question of this moment: are we using AI as a tool, or are we becoming enslaved to it? Key Topics Covered: The CLOC origin story: Building the first legal ops function in Las Vegas gaming and hospitality The CLOC 101 Academy: Why the entry-level program now serves over 150 attendees Slavery vs. freedom: Carl's framing of the choice every legal team faces with AI Personal agency as the answer: Why the automation question is fundamentally about who you want to be The Claude conversation: Why model preference shifts month to month and why the relationship matters more than the tool Fearlessness as career strategy: Why curiosity matters more than credentials 🎧 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://solid.legal/podcasts/ Never eat alone!

Zach Posner sees more legal tech founders than almost anyone alive. As founder of The LegalTech Fund, his portfolio includes over 80 companies. David Cowen sits down with Zach, minutes after Anthropic dropped a major legal partnerships announcement, to unpack the macro view: where we are in the cycle, why talent demand is exploding rather than collapsing, and why the most valuable founders are the ones willing to pivot when the data tells them to. Key Topics Covered: Years happen in days: The investor's frame for the current pace of change The Anthropic announcement: Zach's real-time reaction to twenty-plus legal partnerships and the news that legal is Anthropic's most active power user vertical The trillion-dollar market: Why $300B sits in litigation (the loud part) and $700B in business-as-usual The talent surge nobody is reporting: Software engineer demand up 15.6 percent in twelve months The Pathways Project: Zach's initiative predicting what legal looks like in 2040 Founders who pivot: Why none of the founders Zach meets are doing what they originally said they would TLTF in Scottsdale: Why November's invite-only gathering remains the Davos of legal tech 🎧 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://solid.legal/podcasts/ Never eat alone!

Joe Stephens just helped close a 49-million-dollar raise at steno. He also became a sommelier on the side. David Cowen sits down with Joe, director of legal solutions, law school professor, and one of the most thoughtful voices in litigation technology, to ask the question that defines this moment: what would you not automate? The answer pulls in John Cage, Unreasonable Hospitality, and why curiosity may be the only truly un-automatable skill left. Key Topics Covered: Service vs. hospitality: The distinction that powers steno's brand and why feel beats commodity What Joe would not automate: Physical connection, hugging his kids, walking the dog John Cage's 4'33": Why four and a half minutes of silence is the hardest piece of music ever composed The sommelier hobby: How Joe spends part of his AI dividend on deep human pursuits Listening and curiosity: The two skills Joe tells his students matter more than any technical knowledge Voice to text vs. pen and paper: Why composing a prompt forces slow thinking Unreasonable hospitality: Why delivering experience — not service — is the central differentiator in legal tech 🎧 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://solid.legal/podcasts/ Never eat alone!

Lawyers participate in the downside and never the upside, and Jason Barnwell argues that is the single most important thing about to change. David Cowen sits down with Jason, the former Microsoft GM and associate GC who now leads legal at Agiloft, to unpack why the GC role is being rewritten around upside risk, why contract intelligence is becoming business intelligence, and why the legal leaders selling signal back to the enterprise will earn a seat at the CFO's table. Key Topics Covered: Upside risk vs. downside risk: Why legal moves from brake to accelerator and what that changes Probabilistic practice: Accepting outcomes that are less than perfect to open the aperture on what legal can do at scale Contract intelligence as business intelligence: How aggregated contract data becomes a strategic asset The cut line: How budget conversations reward the best stories — and what legal needs to do to stay above the line Storytelling as leadership: Lessons from Microsoft legends Brad Smith, Neil Suggs, and Hossein Nowbar Selling signal back to the enterprise: Packaging contract data into predictive insights that earn legal upside participation Faster deals as legal's superpower: Why predictive contracting becomes the GC's new currency 🎧 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://solid.legal/podcasts/ Never eat alone!

David Cowen and Ari Kaplan have known each other for twenty years - this is their first podcast together. It is one of the most candid conversations in the series. Ari shares the philosophy that has carried him through two decades at the highest levels of corporate legal, why the US mindset about reclaimed time is a problem worth confronting, and why the most important question of the next decade may be the one Zach Kass asked from the keynote stage. Key Topics Covered: The validation tax: Ari's framework for the time you spend verifying AI output The AI dividend, US edition: Why Americans fill saved time with more work and Europeans leave earlier Permission to stop: David's confession of guilt around saved time and how to reframe it The mentorship moat: Why a Stanford-style simulation program might out-train a senior partner What AI cannot touch: Why high-stakes corporate work still requires human judgment and network Legal as R&D center: Why legal departments are becoming the experimentation hubs of the modern enterprise The renaissance of legal: Why the energy on the CLOC floor in 2026 feels fundamentally different 🎧 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://solid.legal/podcasts/ Never eat alone!

The most honest read on AI adoption in legal might be borrowed from Hemingway: slowly, and then all at once. David Cowen sits down with Adam Becker, director of legal operations at Cockroach Labs, CLOC board member, and one of the architects of the CLOC 101 Academy - to unpack what has actually changed in the last six months, why his team is no longer impressed by AI but expects it, and why the real question is what you are doing with the time AI gives you back. Key Topics Covered: Slowly, then all at once: Why the adoption curve follows the same pattern as every transformational technology before it Capability over efficiency: Why the most important AI gain is being able to do things you literally could not do before The talent surge thesis: Why legal hiring is about to grow, not contract Stratifying the legal stack: NDAs to contract managers, vendor agreements to agents, lawyers to high-stakes work Wordle as a discipline: Why the made bed and the cleaned kitchen are not small things The automated birthday message problem: What we should and should not delegate to our agents The AI dividend list: David's analog notebook of things to do with reclaimed time 🎧 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://solid.legal/podcasts/ Never eat alone!

The pace of change in legal tech is no longer linear - it is exponential. David Cowen sits down with Colin Levy, one of legal tech's most prolific voices, to unpack why we are still at the frontier, why human appetite is failing to keep up with capability, and why daily discipline is the unsung superpower of every leader in this space. Key Topics Covered: Still at the frontier: Why the next five months will deliver more change than all of last year Appetite vs. capability: The widening gap between what AI can do and what humans can absorb The 5:30 AM discipline: Colin's daily writing practice and why a blank page is his most valuable tool Curiosity as a multiplier: Why the people winning right now read the technical guts of AI, not just the headlines The tipping point ahead: Colin's prediction that something big is coming — not a black swan, but a development beyond what anyone is imagining 🎧 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://solid.legal/podcasts/ Never eat alone!

Legal tech used to live in the trunk - pulled out only when something broke. That era is over. David Cowen sits down with Chad Ergun, whose career has spanned Shearman & Sterling, White & Case, and Gibson Dunn before landing at Womble. Chad unpacks why mid-size firms are now competing with BigLaw, why his refusal to lock into a single AI vendor may be the smartest move in legal IT, and why simulation training is replacing the apprenticeship model. Key Topics Covered: Legal tech's promotion: From the trunk to the passenger seat to the driver's seat The roofing contractor problem: Why the billable hour cannot survive predictable outcomes, timelines, and costs Model hopping as strategy: Why Chad runs six different AI models and refuses vendor lock-in Simulation training for associates: Borrowing from pilots and surgeons to fix the mentorship gap AI doesn't judge you: Why associates ask AI the questions they were too afraid to ask their partners Enterprise data sovereignty: Why running AI on your own tenant is non-negotiable The end of the billable hour by 2027: Chad weighs in on Anthropic GC's bold prediction 🎧 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://solid.legal/podcasts/ Never eat alone!

In a market flooded with AI tools, the smartest legal teams aren't chasing technology first - they're slowing down to ask better questions. In this episode of Careers and the Business of Law, David Cowen sits down with Stacy Lettie, James Vinson, and Scott Milner to unpack why design thinking is making a comeback in the AI era. Special shoutout to Nitant Narang for jumping into the conversation and raising one of the most important questions of the episode: when does asking "why" become too much? The conversation cuts through the hype around legal AI and focuses on something far more valuable: defining the right problem before rushing toward a solution. From practical frameworks to real-world failures, the panel explores how legal professionals can think more strategically, collaborate more effectively, and avoid wasting time and money on "shiny software" that doesn't solve the actual issue. Key Topics Covered: Why most legal teams are moving too fast into AI adoption without defining the underlying business problem first The real meaning of design thinking - minus the consultant jargon and buzzwords How asking "Why?" repeatedly uncovers the actual issue hiding beneath the surface The shift from "technology first" back to "people, process, then technology" Why communities like Legal Data Intelligence help legal professionals solve problems faster and avoid reinventing the wheel The importance of prototyping, failing early, and learning through experimentation instead of chasing perfection Why the future value of legal professionals will come from asking the right questions - not just delivering answers 🎧 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://solid.legal/podcasts/ Never eat alone!

LexisNexis CEO Global Legal Sean Fitzpatrick joins David Cowen to break down the new Luminance alliance (200 million contracts meets 200 billion legal documents) and why the legal AI conversation just shifted from "faster and cheaper" to trust-first. If you think AI is collapsing Big Law economics, the data says otherwise. This is a strategic snapshot of where the legal market actually is right now, not where the hype says it should be. Key Topics Covered The Luminance × LexisNexis alliance: built at customer request, not from a boardroom deck Trust-first AI: why efficiency without trust is worthless in legal The three task buckets: a clean framework for where AI actually adds leverage The AI dividend: what GCs are doing with their 10 extra hours a week Rates are climbing, not collapsing: high-single-digit increases across law firms The "manager of agents": the leadership role that doesn't exist yet, but will Career advice for the AI era: take more risks, choose your partners wisely 🎧 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!

The legal department has spent decades as a reactive cost center, called in to fix problems, not prevent them. That's over. In this conversation recorded live at the UDF Lighthouse Customer Forum in Scottsdale, David Cowen sits down with Russ Elmer, General Counsel of ServiceNow, to unpack why 2026 is the year legal transforms from bottleneck to force multiplier, and why the CLO's team is uniquely positioned to become the strategic hub of the entire enterprise. Key Topics Covered: Legal as the enterprise hub: Why the legal department, which touches HR, engineering, finance, and beyond, is better positioned than any other function to generate cross-functional intelligence at scale The bundling/unbundling inflection point: Law firms spent 40 years bundling every knowledge service imaginable. AI is now unbundling all of it, and what's left (judgment, context, relationships) is exactly where great lawyers live The AI dividend: When routine questions and contract redlines get automated, an entire workforce of critically-trained, liberal arts-educated thinkers gets unchained from their desks and unleashed on strategic problems The digital twin concept: Russ shares his vision for a "smarter Russ Elmer," an AI that doesn't just replicate his decisions, but improves on them in real time Brain + arms and legs: Why information alone is worthless without action, and how the ServiceNow partnership is designed to close that gap from insight to outcome The forward-deployed legal engineer: David's framework for the most important career move in legal right now: embed, bridge, build, and grind, because 2026 is the year you either double down or fall behind What legal looks like in 2030: How Russ's team is reimagining org structure, work distribution, and the very definition of what a legal job is   🎧 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 Legalweek 2026, David Cowen sits down with Evan Wong, co-founder and CEO of Checkbox, to unpack a problem most legal teams still haven't solved: legal has software, but it still doesn't have a true operating system. This episode gets into why intake remains broken, why legal ops is becoming one of the most important roles in the business of law, and why the next wave of AI value will come from embedding legal into the tools the business already uses. Hosted by David Cowen Key Topics Covered Why Evan built Checkbox to become the operating system for legal, not just another point solution The core problem Checkbox solves: legal intake is still messy, manual, and invisible across most organizations Why the first major champions of this category were legal ops leaders who understood legal as a business function How Checkbox evolved from a no-code workflow tool into a system of record and front door for legal Why the future of legal intake is not forms and ticketing systems, but AI embedded into email, Slack, Teams, Salesforce, and everyday workflows Evan's view that the GC is increasingly a wartime role, creating space for legal ops to evolve into a more strategic chief-level business function A hard truth about the market right now: the biggest challenge is not lack of tools, but too much noise, too many AI labels, and not enough clarity on what to implement first 🎧 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 Legalweek 2026, David Cowen sits down with Curt Sigfstead, CFO of Clio, to unpack how one of legal tech's longest-running companies is moving upmarket and redefining what AI should do inside legal operations. The conversation centers on a major shift now underway: from software that assists lawyers to AI-powered teammates that qualify leads, streamline operations, and help law firms and legal departments rethink the way legal work actually gets done. Hosted by David Cowen Key Topics Covered Why Clio's origin story matters now: a company built for the cloud in 2008 is using that long-view advantage to enter the enterprise market at the right moment How Clio grew from serving solo and small firms to supporting a massive global footprint with 400,000 users across 130 countries Why the next legal AI opportunity is not just better research or drafting, but connecting legal work with the operational systems around it Clio's core argument for the future: AI should not just assist lawyers, it should perform tasks and move work forward A real example of AI in action: using AI to intake leads, qualify them, check conflicts, summarize issues, and save attorneys hours before the first call Why Kirk believes today's fragmented categories - research, document management, and AI tools - will eventually collapse into a more unified legal workflow The enterprise pitch: large law firms and corporate legal departments need partners who understand both the practice of law and the operations of legal service delivery 🎧 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!

Recorded live from Legalweek, David Cowen sits down with Patrick Forquer, the CRO of Legora, to unpack what happens after the AI experimentation phase ends. The legal industry is shifting from curiosity to proof, where firms and corporate teams are demanding measurable ROI, faster workflows, and real business impact. The big takeaway: the real AI dividend isn't just saving time - it's accelerating work, improving outcomes, and unlocking revenue that used to sit trapped inside slow legal processes. Hosted by David Cowen Key Topics Covered Why legal AI has moved from experimentation to social proof, with firms now demanding measurable ROI instead of demos and hype The three layers of the AI dividend: saving time and cost, increasing the quantity and quality of work, and ultimately generating new revenue How faster contract cycles can unlock enterprise value by accelerating revenue rather than just reducing legal spend Why the smartest buyers cut through market noise and choose AI tools based on workflow fit and adoption readiness The new implementation reality: AI success requires post-sale enablement, legal engineers, and real operational change Why AI adoption is now a cross-functional decision involving leadership, innovation teams, knowledge management, and practitioners The talent shift underway as firms look for professionals who can bridge legal expertise with AI-driven execution 🎧 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 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 🎧 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 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 🎧 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 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 🎧 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 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 🎧 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!

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 🎧 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 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 🎧 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 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 🎧 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!

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: <a id="menur4ds" class= "fui-Link ___1q1shib f2hkw1w f3rmtva f1ewtqcl fyind8e f1k6fduh f1w7gpdv fk6fouc fjoy568 figsok6 f1s184ao f1mk8lai fnbmjn9 f1o700av f13mvf36 f1cmlufx f9n3di6

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!