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 gov...

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...

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...

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...

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...

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 re...

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:...

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 somet...

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...

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...

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 curios...

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...

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...

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 r...

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...

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 simula...

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 conve...

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 uniquel...

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 co...

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...

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 accelerati...

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, con...

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 precisio...

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 emb...

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...