Careers and the Business of Law – Détails, épisodes et analyse

Headed to CLOC? So are E.J. Bastien and David Cowen and this episode is your field guide.

Before you start speed-walking the ARIA hallways and hunting for coffee and co-pilots, listen in. E.J. Bastien has spent two decades at Microsoft reimagining what in-house eDiscovery and litigation support can be. He’s leading teams, building AI agents, and solving tomorrow’s problems with tools that most legal teams haven’t even touched yet.

In this pre-CLOC masterclass, we dig into:

• How Microsoft is using GenAI to streamline review, code documents, and surface case-critical facts before a human ever sees them
• What it really means to build a bespoke agent trained on your legal team’s workflows not ChatGPT, but your playbook
• Why perfectionists are out, and “learn-it-alls” are in and how that mindset shift is the secret to surviving (and thriving) in 2025.

You’ll also hear what it takes to lead with confidence, experiment without fear, and stay grounded in the face of constant change.

It's Vegas. It's CLOC. It’s time to stop chasing answers and start trading playbooks.

🎧 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!

Guest: Kevin Cohn, Chief Customer Officer, Brightflag
Host: David Cowen, President, The Cowen Group

🎙 This episode of Careers in the Business of Law (CBL) is a masterclass in motion.

Pre-live from the frontlines of CLOC, Kevin Cohn—Chief Customer Officer at Brightflag—joins David Cowen for a candid, strategic breakdown of how legal ops careers are being redefined in real time.

It’s not just theory. Kevin unpacks the real ROI of relationship-driven events, the anatomy of modern go-to-market strategy, and the emergence of legal ops as a strategic powerhouse inside the legal department.

🔑 Six Big Ideas from the Conversation

1. Community-first is the new go-to-market.
Bright Flag doesn’t lead with features—they lead with helping. Their playbook is about solving legal ops problems, not pitching products.

2. Events like CLOC drive Origination, Advancement, and Nurturing.
Think beyond booth traffic. Kevin outlines how events create momentum across the business development lifecycle—and why deep trust matters most.

3. Legal ops roles are moving up the strategy stack.
Titles like Chief Legal Data Officer and Legal Chief Strategy Officer mark a shift from execution to foresight. Legal ops is no longer the backstage crew—it’s co-authoring the future.

4. The champion persona is your north star.
Champions are the change agents inside legal departments. They may not control the budget, but they drive the decision.

5. First-time CLOC attendee? Come with a plan.
Ask questions. Introduce yourself. Set daily KPIs for connection. And before the rooftop parties blur your memory, write those names down.

6. Legal ops is leading the AI era.
While GCs are pulled into geopolitical and enterprise-wide risk, legal ops is best positioned to own digitization, AI integration, and operational change.

Viva Las Vegas. Let’s move from now to next.

Ever wonder how to build a career worthy of a Lifetime Achievement Award? My latest guest, Jay Leib, has done exactly that—and he's here to share how.

From his early days in software sales at RTI, to leadership roles at EY, Relativity, NextLP, and now Reveal, Jay has built his career through radical curiosity, relentless networking, and entrepreneurial grit.

We cover Jay’s jungle gym-like career moves, why curiosity and communication matter more than certifications, and the hacks that helped him create lasting connections—from LinkedIn coffee meetings to mentorship lessons from VC icon Troy Henikoff.

🎧 Tune in for:

• Jay's entrepreneurial story of "cash in, cash out" (and how he learned to handle cash flow stress).
• How answering "rows and columns" in a job interview changed his life.
• Career-defining lessons from EY and Relativity, including the power of focus and punctuality.
• Networking pro tips (and how he credits career success to LinkedIn outreach).
• Jay’s weekend curiosity hacks: AI tools (ChatGPT, Claude, Gemini) and lifelong learning.

🎧 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/

Legal teams aren’t just tracking data—they’re driving business decisions with it. Today, I sit down with Dave Bernstein, Executive Director, Analytics at Wells Fargo, to unpack the rise of Legal Data Intelligence (LDI) and why it’s changing everything.

Dave shares his unconventional path from 18 years in shipping to legal analytics, how he built a data-driven legal department alongside leaders like Kim Wolf, Edward L., and Tim Davenport, and why AI tools like Microsoft Copilot are set to revolutionize legal work.

💡 One Big Idea: The best legal ops teams don’t just analyze what happened—they predict what’s next.

🎯 What You’ll Learn in this episode:
✅ How Wells Fargo built a high-impact legal data intelligence team
✅ The must-have skills for legal ops professionals (from meta-skills research by Julia Hasenzahl & Brian Meegan at ProSearch)
✅ Why AI won’t replace legal teams—but will replace the ones who don’t adapt (Microsoft Copilot is a game-changer)
✅ The truth about talent transformation—who thrives, who doesn’t, and why (Farrah Pepper & Adam Rouse are leading the way)
✅ The future of legal ops roles (Chief Legal Data Intelligence Officers are on the rise)

📚 Books Mentioned
📖 Be Data Analytical – Jordan Morrow
📖 Be Data Literate – Jordan Morrow

🚀 What’s Next? Meet Dave in Person
Join Dave Bernstein at SOLID Atlanta (Nov 4, 2025) alongside Kim Wolf, Farrah Pepper, and other legal ops leaders as they shape the future of LDI.

🔗 Register for SOLID Atlanta → https://solid.legal/solid-atlanta-2025/

🎧 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/

Legal work isn’t just about managing data—it’s about unlocking intelligence. AI, eDiscovery, and Legal Data Intelligence (LDI) are transforming how firms analyze, predict, and strategize. Are you keeping up?

In this episode, Robert Keeling (Partner, Redgrave LLP) joins David Cowen to unpack how AI, legal data intelligence, and next-gen eDiscovery are transforming the legal industry.

🔹 From Paper to AI: How legal data moved from printed emails to Slack, chat, and AI-powered discovery.
🔹 The AI-Powered Law Firm: Will firms create AI associates like Goldman Sachs?
🔹 Legal Work in 2025: AI isn’t replacing lawyers—it’s changing who does what and how.
🔹 The AI Dividend: How AI is helping legal teams work smarter, reduce stress, and focus on strategy.
🔹 Order to Chaos: How Legal Data Intelligence (LDI) is bringing structure to the AI revolution.

🔔 Tap play now to future-proof your legal career—or risk falling behind.

💡To learn more about the future of legal innovation, visit https://cowengroup.com/

📢 The legal industry is at a tipping point. Are you ready? In this episode, David Cowen sits down with Ted Theodoropoulos, Founder & CEO of InfoDash, to unpack the biggest shifts redefining law firms, legal tech, and knowledge management.

From AI-powered legal services to the VC-style approach to tech investment, this conversation is packed with insights that will help you future-proof your career and your firm.

🔥 What You’ll Learn:
✅ The AI Wake-Up Call: How AI is pushing law firms to rethink innovation, risk, and business models
✅ Beyond Billable Hours: Why firms are shifting from revenue growth to margin expansion and efficiency
✅ The VC Playbook for Law Firms: How firms like Paul Hastings, Sullivan & Cromwell, and Seyfarth Shaw are investing in legal tech startups
✅ KM as a Profit Center: How Ogletree Deakins turned knowledge management into a seven-figure revenue stream
✅ Who’s Leading the Charge? Why firms like Wilson Sonsini (Neuron) and Cooley (Cooley Go) are redefining how legal services are delivered
✅ Career Acceleration: Why lifelong learning, adaptability, and intellectual horsepower are now table stakes

🎯 Who Should Listen?

• KM, Legal Ops, eDiscovery & AI Leaders looking to stay ahead of the curve
• Lawyers & Legal Professionals navigating tech disruption
• Legal Tech Founders & Entrepreneurs building the next big thing
• Anyone interested in how law firms are evolving in the AI era

🔗  Legal Innovation & KM Leaders Mentioned:
🔹 Joe Green (Chief Innovation Officer, Gunderson Dettmer)
🔹 Esther Bowers (KM & Innovation Expert)
🔹 Ed Macnamara (Chief Innovation Officer, ArentFox Schiff)
🔹 Wendy Curtis (Chief Innovation Officer, Orrick)
🔹 Lorie Almon (Chair and Managing Partner, Seyfarth Shaw)

📚 Books Mentioned:
📖 Legal Upheaval by Michele Destefano
📖 The Leader Upheaval Handbook by Michele Destefano
📖 Innovation in Law Firms: Implementing Successful Projects by Stuart Whittle & Catriona Wolfenden

📅 Join the Conversation:
🔥 The Cowen Café – Weekly roundtables on AI, legal careers & innovation
🎤 Legal Week NYC – Meet David & Ted in person at the industry’s biggest event

🎧 Subscribe, Rate & Share!
If this episode sparked new ideas, subscribe, review, and share with your network.

📍 Apple Podcasts | Spotify 

And remember: Never eat alone. 🚀

#LegalTech #KM #Innovation #FutureOfLaw #AI #LegalOperations #LawFirmLeadership

In this episode, David Cowen sits down with Nicole Giantonio, SVP and Chief Marketing Officer at Epiq, to explore how cutting-edge AI technology, bold investments, and strategic talent development are revolutionizing the legal industry. From Epiq’s game-changing AI Labs to Nicole’s private equity perspective on innovation, this conversation is a masterclass for anyone navigating the evolving world of legal services.

If you’re ready to future-proof your career and understand the forces shaping the next decade of law, this episode is your roadmap.

What’s Inside?

The Talent Shift: Nicole shares how AI is reshaping roles, creating higher-level opportunities, and why training with AI tools is non-negotiable for today’s professionals.

Boardroom Trends: Why Fortune 500 companies and Global 1000 law firms are making massive investments in legal tech—even without a clear ROI.

The Iceberg Effect: Nicole’s analogy explains the hidden creativity and acceleration beneath the surface of the legal industry—and why it’s gaining momentum.

Future of Legal Ops: Get a sneak peek into emerging trends like legal data intelligence, the role of agentic AI models, and how Epic is positioning itself for long-term innovation.

🎧 Love what you heard? Don’t forget to like, share, and subscribe to Careers in the Business of Law on Apple Podcasts, Spotify, or wherever you get your shows. Let’s take your career from now to next. And remember—never eat alone.

Episode Description:
In this episode, David Cowen speaks with Bobby Malhotra, Partner at Winston & Strawn and a founding member of Legal Data Intelligence (LDI). Together, they explore how AI, eDiscovery, and data governance are reshaping the legal industry. Bobby also highlights the power of mentorship, the evolution of legal data intelligence, and the lessons he’s learned from his own career journey. If you’re navigating the future of law, this conversation is a must-listen.

What’s Inside?

• eDiscovery’s Next Chapter: Bobby dives into how the field has evolved from email production to a sophisticated practice that influences case outcomes and strategies.
• The Role of AI in Legal Data: Discover how conversational AI is eliminating friction, accelerating time to insights, and revolutionizing how legal teams manage data.
• Legal Data Intelligence (LDI): Learn about the founding and mission of LDI, a professional network designed to tackle the most complex data challenges across disputes, transactions, and compliance.
• Mentorship and Leadership: Bobby shares how mentorship transformed his career and why building relationships with mentors and mentees is critical to success in the legal profession.
• Going Above and Beyond: Bobby recommends Unreasonable Hospitality by Will Guidara as a blueprint for creating extraordinary client experiences.

Key Mentions:

• Books: Unreasonable Hospitality by Will Guidara
• Influencers: Kathleen McDowell, John Rosenthal, and Scott Cohen
• Organizations: Legal Data Intelligence (LDI), and  Winston & Strawn

Takeaways

• Leverage AI Tools: Start using conversational AI like ChatGPT to interrogate your data and uncover insights faster.
• Mentorship Matters: Find mentors who align with your goals and reciprocate by sharing your own expertise.
• Join Professional Networks: Get involved with groups like LDI to connect with industry leaders and stay ahead of emerging trends.

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!

In this episode, David Cowen dives into the transformative role of Legal Data Intelligence (LDI) with industry leaders Julia Hasenzahl, Jeremiah Weasenforth, and Ashley Christakis. They discuss how meta-skills like strategic thinking and adaptability are reshaping legal operations and explore how experiential knowledge is driving predictive insights across the legal ecosystem.

Key Topics:

• Meta-Skills Matter: Why adaptability, curiosity, and problem-spotting are essential for thriving in LDI.
• Expanding Roles: How LDI professionals are integrating e-discovery, governance, privacy, and risk management.
• Building Talent: The importance of fostering a culture of radical thinking to attract top talent in a competitive market.
• Better vs. Different: The dual need to improve current processes while rethinking how legal data is used to create predictive strategies.

Meet the Guests:

• Julia Hasenzahl : Co-founder and CEO of ProSearch, a leader in applying data intelligence to legal operations and e-discovery.
• Jeremiah Weasenforth: Legal Analytics Director at Edward Jones, pioneering data-driven approaches to legal strategy.
• Ashley Christakis: Senior Manager eDiscovery and Legal Operations at CrowdStrike, innovating the intersection of e-discovery and operational excellence.

Subscribe and Share:
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Take your career from now to next. Never eat alone.

In this episode, David Cowen chats with Kevin Cohn, Chief Customer Officer at Brightflag, about how next-gen technology and AI are reshaping legal operations, the war for talent, and the evolving role of legal professionals. If you’re navigating the future of law, this conversation is your roadmap.

What’s Inside?

• Brightflag’s Impact: Learn how Brightflag uses AI to transform legal billing and matter management for clients like Spotify and SAP, enabling legal teams to shift from admin to strategy.
• Tech & Talent Arms Race: Why GCs are hiring legal ops pros first and how AI is disrupting lower-level work while increasing demand for top talent.
• OKRs in Action: Kevin shares insights from Measure What Matters by John Doerr and how OKRs drive long-term innovation at Brightflag.
• Future-Proofing Your Career: Why training with AI tools like ChatGPT is critical to stay competitive in 2025 and beyond.

Key Mentions -

• Books: Measure What Matters by John Doerr
• Influencers: Tomasz Tunguz, Dave Kellogg, Daniel Young (Shark Ninja), Eva Bogucki (Cargill).
• Podcasts: Brightflag’s legal ops podcast hosted by Alex Kelly.

Takeaways -

• Train with AI: Spend an hour a day with tools like ChatGPT or Gemini to stay ahead.
• Build Your Network: Surround yourself with thinkers and tech leaders to sharpen your career edge.
• Think Long-Term: Apply OKRs to stretch your goals and align them with future trends.

Quotes -

• "If you’re not training with AI, you’re falling behind." – Kevin Cohn
• "Your career is a jungle gym, not a ladder—never eat alone and think out loud with others." – David Cowen

🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next!