Careers and the Business of Law

Hosted by David Cowen

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Jun 2026

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About the show

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".

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June 9, 202632 min

AI Governance Is the New Career White Space in Law: Bobby Malhotra on the Rise of the Tech-and-Data Lawyer

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 MENTIONED David Cowen - Host Bobby Malhotra - Litigation Partner; Chair of eDiscovery and Information Governance; AI Strategy Group Member; Founding Member of Legal Data Intelligence Melanie Prevost - Referenced in connection with career creation and emerging opportunities Malcolm Gladwell - Referenced in connection with the 10,000-hour rule COMPANIES & ORGANIZATIONS MENTIONED Winston - Bobby's firm Legal Data Intelligence / LDI - Community and framework for legal data professionals IAPP - AI governance and privacy education resource CLOC, ILTA, SOLID - Legal operations, innovation, and business of law communities M365, SharePoint, cloud platforms, data lakes, and metadata - Referenced as examples of where organizational data lives Colorado, Connecticut, Illinois, California, and Texas - Referenced in connection with emerging AI legislation EU AI Act - Referenced in connection with AI regulatory obligations NAIC - Referenced in connection with AI guidance in the insurance industry New York DFS - Referenced in connection with regulated financial institutions 🎧 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!

May 27, 202635 min

From Legal Ops to Business Ops: Mark Allen on AI, Career Growth and the Future of the Function

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 & ORGANIZATIONS MENTIONED Zillow Group — Mark's current company Netflix, Activision Blizzard — Previous buyer-side roles Brightflag, CloudCourt — Mark's vendor-side experience CLOC — Legal ops community; CLOC Core 12 referenced; CLOC.org Solid, Running Legal Like a Business, Legal Week, ILTA — Legal ops education and community events 🎧 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!

May 25, 202625 min

Confident Curiosity: Oyango Snell on Legal Ops, AI and the Future of CLOC

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 & CEO of CLOC, for a post-CGI debrief. The energy on the floor was unmistakable: this is not the same industry it was twelve months ago. From Second City opening every morning to standing-room-only sessions on AI maturity, CGI 2026 signaled that the legal ops community has moved from anxiety to confident curiosity. WHY THIS MATTERS The legal industry is no longer asking if AI matters. It's asking how to measure it. With budgets flat and demand rising, legal ops professionals are being forced to get strategic. This conversation captures the mood of the market and where the next five years are headed. KEY TAKEAWAYS Attendees came with hands-on experience and real questions. Anxiety is out, confident curiosity is in. Legal ops has moved from chaos to at least ad hoc, if not operational, on the maturity arc. "Do more with less" is hogwash. Flat budgets plus rising demand requires strategy, not just effort. AI won't replace jobs. People who leverage AI will replace those who don't. A growing economy means more demand for legal services. The doomsday narrative doesn't hold up. Education is the new currency. CLOC Academy is hitting the road to reach those who can't make it to CGI. Legal ops sits at the intersection of law and technology. That's the superpower. Own it. CGI 2027 is back at the Aria in Las Vegas. Pro tip from David: Thank the speakers. Easiest networking move there is. Pro tip from Oyango: Own your professional stake. Relationships are built through follow-up, not just introductions. PEOPLE MENTIONED David Cowen, Host Oyango Snell, President & CEO, CLOC Kevin Clem, Harbor; co-author of the State of the Industry Report Zach Kass, CGI 2026 Keynote Speaker Mary O'Connell, Market leader, referenced Connie Brenton, Founder and CEO, LegalOps.com COMPANIES & ORGANIZATIONS MENTIONED CLOC, Corporate Legal Operations Consortium; host of CGI and legal ops community anchor Harbor, Co-produced the 2026 State of the Industry Report with CLOC Second City, Opened each day of CGI 2026 and set the tone for the conference Anthropic, Ivo, OpenAI, Among the vendors actively hiring legal tech talent SOLID, Legal career and education community; Solid New York on October 1st CLOC Academy, Educational arm of CLOC, now going on the road beyond CGI 📅 Mark your calendar: SOLID New York, October 1st in New York City 📊 Get the 2026 State of the Industry Report at the CLOC website or Harbor's website. 🎧 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!

May 22, 202641 min

From Chaos to Operational: How Legal Teams Are Navigating the AI Maturity Arc

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 workflows Legal Data Intelligence (LDI) - Community behind this series; legaldataintelligence.org 🎧 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!

May 19, 202630 min

THE INFRASTRUCTURE LAYER OF THE BUSINESS OF LAW WITH TOM BALDWIN

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&A) are wide open. Practice of law got all the attention. A data lakehouse unifies data across 20-40 systems. Snowflake popularized it; 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 & CEO Andrew Sieja- Founder of kCura/Relativity; 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 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!

May 18, 202619 min

200M Contracts Meets 200B Legal Documents: Inside the LexisNexis-Luminance Alliance

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!

May 14, 202614 min

Up by 5:45, Thinking by 6: The Executive Discipline That Built a State Street Career

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!

May 14, 202618 min

Give Alexander Hamilton a Typewriter: The Reframe That Makes Change Management Actually Work

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!

May 14, 202613 min

Slavery to AI or Freedom Through It? The Choice That Defines the Next Decade

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!

May 14, 202614 min

Years Happen in Days: The Investor's-Eye View of Legal's Trillion-Dollar Transformation

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!