Careers and the Business of Law

David Cowen
  • 5.0 (10)
  • CAREERS
  • UPDATED WEEKLY

Welcome to Careers in The Business of Law with David Cowen, the podcast series designed to elevate and accelerate the careers of legal professionals. David aims to provide insightful and inspiring career stories from industry insiders, law firm leaders, corporate law department executives, and legal technology business leaders. This podcast will provide you with an inside look into the career journeys of some of the most successful and influential leaders in the legal field. You will gain actionable insights into their experiences, challenges, and triumphs through these discussions. Recognizing that the legal profession is constantly changing, David wants to ensure that you have the knowledge and tools necessary to navigate this evolving landscape. David's guests will provide insights on topics such as emerging technologies, legal operations, and leadership strategies, which will help you accelerate your career growth and success. David's goal is to create and inspire a community of legal professionals who are dedicated to learning, growing, and advancing their careers. Whether you are a law student, young professional, or seasoned veteran, this podcast series is for you. Join David and his guests as they explore the stories and insights that shape the legal profession, and help you take your career to the next level. If you enjoy this podcast, please subscribe on Spotify, Apple iTunes, or wherever you get your podcast, and remember "Never Eat Alone".

  1. Legal Just Left the Basement: How AI Is Making the CLO the Most Powerful Person in the Room

    MAR 27

    Legal Just Left the Basement: How AI Is Making the CLO the Most Powerful Person in the Room

    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!

    23 min
  2. Legal Doesn't Need More AI Tools - It Needs an Operating System

    MAR 25

    Legal Doesn't Need More AI Tools - It Needs an Operating System

    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!

    24 min
  3. Legal AI Is Moving Beyond Copilots - Clio Is Betting on Teammates That Actually Do the Work

    MAR 24

    Legal AI Is Moving Beyond Copilots - Clio Is Betting on Teammates That Actually Do the Work

    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!

    20 min
  4. The AI Dividend Is Real - But Only If Legal Teams Turn Speed Into Revenue

    MAR 23

    The AI Dividend Is Real - But Only If Legal Teams Turn Speed Into Revenue

    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!

    28 min
  5. Legal Tech Isn't Chasing Hype Anymore - It's Rewiring Litigation Budgets, Workflows, and What In-House Teams Keep

    MAR 20

    Legal Tech Isn't Chasing Hype Anymore - It's Rewiring Litigation Budgets, Workflows, and What In-House Teams Keep

    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!

    22 min
  6. Lawyers Don't Need Another AI Tool - They Need an Ally Inside the Contract

    MAR 19

    Lawyers Don't Need Another AI Tool - They Need an Ally Inside the Contract

    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!

    26 min
  7. Legal AI Is Growing Up Fast - And Workflows, Not Prompts, Will Decide Who Wins

    MAR 18

    Legal AI Is Growing Up Fast - And Workflows, Not Prompts, Will Decide Who Wins

    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!

    14 min
  8. Why AI Alone Won't Win in Legal: Dennis Garcia on Trust, Speed, and the Human Edge Live from Legalweek

    MAR 17

    Why AI Alone Won't Win in Legal: Dennis Garcia on Trust, Speed, and the Human Edge Live from Legalweek

    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!

    25 min
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About

Welcome to Careers in The Business of Law with David Cowen, the podcast series designed to elevate and accelerate the careers of legal professionals. David aims to provide insightful and inspiring career stories from industry insiders, law firm leaders, corporate law department executives, and legal technology business leaders. This podcast will provide you with an inside look into the career journeys of some of the most successful and influential leaders in the legal field. You will gain actionable insights into their experiences, challenges, and triumphs through these discussions. Recognizing that the legal profession is constantly changing, David wants to ensure that you have the knowledge and tools necessary to navigate this evolving landscape. David's guests will provide insights on topics such as emerging technologies, legal operations, and leadership strategies, which will help you accelerate your career growth and success. David's goal is to create and inspire a community of legal professionals who are dedicated to learning, growing, and advancing their careers. Whether you are a law student, young professional, or seasoned veteran, this podcast series is for you. Join David and his guests as they explore the stories and insights that shape the legal profession, and help you take your career to the next level. If you enjoy this podcast, please subscribe on Spotify, Apple iTunes, or wherever you get your podcast, and remember "Never Eat Alone".

Information

  • Creator
    David Cowen
  • Years Active
    2023 - 2026
  • Episodes
    126
  • Rating
    Clean
  • Copyright
    © 2023, David Cowen, All Rights Reserved
  • Show Website
    Careers and the Business of Law

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