Careers and the Business of Law

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

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💡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

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💡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:

• Scott Milner – Recognized for bridging deep technical expertise with practical leadership in eDiscovery and regulatory strategy
• Greg Mazares – ModeOne board member and trusted mentor, shaping how technology is applied to real client problems
• Jerry Bui (Purpose) – Cited for his perspective on the growing importance of forensics in modern legal workflows
• Nathaniel Whittemore – Host of The AI Daily Brief, referenced for framing the MIT insight on task-level automation
• Joseph Pochron – Nardello, recommended as a future guest for his visibility into corporate investigations and compliance
• Anthony Cardine – O'Melveny & Myers, highlighted for his leadership at the intersection of eDiscovery, paralegal teams, and operational change

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💡To learn more about the future of legal innovation, visit https://cowengroup.com/ Never eat alone!

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

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💡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.

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💡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.

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💡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.

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💡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!