The way litigation has been practiced for decades is cracking - and the lawyers who see it first will win.

Recorded live at Legalweek 2026, host David Cowen sits down with Jeffrey Chivers, CEO of Syllo, to unpack why AI isn't just automating legal tasks - it's collapsing the traditional litigation workflow entirely. The path from discovery to trial-ready strategy is getting shorter. The question is: which legal professionals will adapt in time?

What you'll learn:

• Why the litigation AI market has officially matured - and who's winning
• How Syllo was built by a litigator for litigators, not as a generic platform
• Why the old step-by-step workflow is dead - and what's replacing it
• What associates are really feeling right now, and what they need to hear
• Why 2025–2026 may be the most career-defining window in modern legal history

🎧 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!

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

🎧 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 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!

Welcome to this special episode of "Careers and the Business of Law." Today, we're taking a nostalgic journey down memory lane. Can you imagine a time in eDiscovery when it revolved around boxes of paper, scanning documents, and visits to copy shops? That was the reality for our esteemed guests, Ian Campbell of iConnect and Tom Morrissey of Purdue Pharma. Both Tom and Ian entered the eDiscovery world when it was still in its nascent stages, and they've witnessed its evolution firsthand.

Join us as they share tales of the past, drawing parallels and contrasts to today's digital age, and offering insights into what the future might hold. Whether you're a newcomer to the field or a seasoned professional, this episode promises to be a delightful blend of nostalgia and forward-looking predictions. For more on evolving trends, careers and the business of law, as well as our private events, workshops, and conferences, please follow the Cowen Group at www.cowengroup.com

Description: This week, we're diving deep into the world of law firm innovation – and it's not about the latest tech or software. Our focus today is on the human side of things: talent, culture, and change management. I'm excited to introduce two pioneering guests who are leading the charge in reimagining what the modern law firm can be. Madeline shares her origin story, discussing her background from Panama and wanting to be a maritime lawyer to her becoming the innovation leader at Reed Smith.

Tim talks about his early aspirations to be a fighter pilot, actually being a mailman and pizza delivery guy and his transition into law, eventually leading Ogletree's practice intelligence group to focus on data analysis and innovation. Growing that group from 1 to 30 plus. This is one winding road of unexpected twists and turns. Both discuss the importance of change management vs project management and user engagement in driving adoption of innovative solutions in the legal industry. It's all about the talent.

The interview concludes with a discussion about favorite bands and songs. Wrap-up:

It's clear that the landscape of law is changing, not just in terms of the technologies we use but more fundamentally in how we think about talent, culture, and change. A big thank you to Madeline Boyer and Tim Fox for sharing their insights and innovative approaches.

For more on evolving trends, careers and the business of law, as well as our private events, workshops, and conferences, please follow the Cowen Group at www.cowengroup.com

From wanna-be quarterback at Notre Dame to box delivery at Chicago Legal Copies to the Founder and CEO of one of the world's most successful eDiscovery software companies.

Wendell and I discuss:

His first job and the rearview mirror

The legal landscape over the next 3 years

The workforce of the future and talent on the rise

The benefits and risks of private equity

In office vs. remote vs. hybrid work cultures

Advice to start-ups 

Role models and industry leaders that inform and inspire with shout-outs to:

Dave Copps, Eddie Sheehy, John Davenport, Florinda Baldrige, Sophie Ross, Todd Marlin, Andy McDonnell 

For more on evolving trends, careers and the business of law, as well as our private events, workshops, and conferences, please follow the Cowen Group at www.cowengroup.com

Join me for an insightful chat as we delve into the life and journey of Haresh Bhungalia. From his childhood dreams of soaring the skies as a pilot to his adventures in Big 4 consulting and entrepreneurial pursuits. We'll touch upon:

Visioning the future of legal business by 2030

• His take on the surge of new legal tech software players
• The evolving role of legal operations in today's world and the future
• Advice for budding legal tech entrepreneurs
• The unique edge that sets Casepoint apart

For more on Cowen Podcasts, Career Coaching, and Leadership Networking Events, please visit the Cowen Group on LinkedIn :https://www.linkedin.com/company/the-cowen-group/?viewAsMember=true

Join me for an insightful chat as we delve into the life and career journey of AJ Shankar. From his distinguished academic career in computer science and graduating magna cum laude from Harvard to pioneering Everlaw as a successful entrepreneur. Our conversation will cover:

• The significance of the Harvard Barnwell Award
• Insights into the Berkeley startup ecosystem 
• A glimpse into the future of eDiscovery software
• What sets Everlaw apart in the competitive landscape
• Valuable insights for for eDiscovery and legal operations enthusiasts
• AJ's perspective on the future landscape of the business of law.

Insights into the Berkeley startup ecosystem  A glimpse into the future of eDiscovery software What sets Everlaw apart in the competitive landscape Valuable insights for for eDiscovery and legal operations enthusiasts AJ's perspective on the future landscape of the business of law. For more on Cowen Podcasts, Career Coaching, and Leadership Networking Events, please visit the Cowen Group on LinkedIn :https://www.linkedin.com/company/the-cowen-group/?viewAsMember=true

Andy Wilson: Founder & CEO of Logikcull

Who are the top 6 eDiscovery software CEOs? 

If I say Apple - you say Steve Jobs

If I say Amazon, you say Jeff. If I say Tesla, Microsoft or GE you say Elon, Bill and Jack.

But, what if I say, Logikcull, Relativity, Disco, Everlaw, Reveal or Casepoint?

Join me this summer as I interview the top founders and CEO's in the Legal software space starting with the Big 6 of eDiscovery.

In this episode- Andy Wilson founder and CEO of Logikcull.

Andy and I discuss:

Andy Wilson's Background and Education 9:24

Andy Wilson shares his childhood dream of being his own boss and his love for reading comic books and sci-fi. He also talks about his interest in art and how he eventually switched from English and psychology to computer science and then to management science, which combined his interests in both business and software.

Market Velocity and Business Model Comparison 11:31

David Cowen and Andy Wilson discuss the varying rates of change in different market sections and the slow adoption of modern technology. They also compare their business model to their competitors, highlighting their democratization ethos and unique bimodal purchasing options. Wilson uses the analogy of selling water to a building on fire to describe their event-driven market.

• Business model compared to competitors14:37

Identifying Superpowers 17:30

David Cowen leads a discussion on identifying superpowers among the CEOs present. He asks Andy Wilson about his specific superpowers and Wilson shares that he excels in designing easy-to-use systems and making them accessible to customers. Cowen also asks Wilson for advice for law firms and corporate law departments starting their journey in exploring next-gen technology in the e-discovery space.

Cybersecurity Threats to Law Firms and Disrupting Incentive Structures 20:06

David Cowen and Andy Wilson discuss the cybersecurity threats faced by law firms and the need to invest in secure modern technology to handle clients' data. They also talk about the impact of AI on the legal industry and the need to disrupt incentive structures to adapt to the changing landscape.

Commercial Break and Logical Advertisement 26:08

During a break in the meeting, David and Andy do a humorous commercial for Logikcull.

The Impact of Automation on Job Creation 28:40

David Cowen and Andy Wilson discuss the potential impact of automation on job creation, citing McKinsey's report that for every job destroyed during the internet boom, 2.6 jobs were created. They express optimism about the future and discuss the potential for automation in the legal space, including the creation of roles such as legal engineers and chief AI officers. They also discuss the potential for automation to make the law easier to understand and for non-technical attorneys to do good work.

The Future of Legal Services 32:37

David Cowen and Andy Wilson discuss how the mission of Logikcull, is to democratize legal services and make it more accessible to the general population. They predict that the demand for legal services will increase as the cost decreases and access becomes easier. They also discuss the possibility of a new breed of lawyers emerging, specializing in areas such as drone litigation.

The Market and Entrepreneurship 38:04

David and Andy discuss the changing landscape of entrepreneurship and the ability for startups to compete with fewer resources. 

For more on Cowen Podcasts, Career Coaching, and Leadership Networking Events, please visit www.Cowengroup.com

Brian Corbin and Ed Sohn share their ex-pat experiences and how it's impacted their careers and families. They discuss the similarities and differences between working in the US and abroad, the challenges and opportunities that come with it, and the complex experiential knowledge that one gains from working abroad. 

They also talk about the disruptive force of AI in the legal industry and the need for businesses to invest in human capital that is resilient to this force.

Finally, we explore the future of the legal industry and the net new demand for legal talent and services that may arise in the future. 

Key Questions

• How did you get from your childhood dream job to where you are now?6:16

• What skillset or aptitude is required to take an expat assignment?12:38

• How did your experience in India shape your perspective on global legal services?16:40

• What opportunities do you see for growth in the legal industry?26:20

For more on evolving trends and careers and the business of law, please follow the Cowen Group on LinkedIn :https://www.linkedin.com/company/the-cowen-group/?viewAsMember=true

Join us in this episode as we delve into the remarkable journey of David Wang, Chief Innovation Officer at Wilson Sonsini, as he navigates the challenges of defining his role in the legal industry. From humble immigrant beginnings and his mother's Chinese restaurant, David's path has led him to become one of the pioneering chief innovation officers in the legal field.

In this captivating conversation, David shares his insights on the crucial role of a CINO and the profound impact of NextGEN technology on the business of law. As he eloquently explains, while the larger law firms may weather the storm, the rest of the industry will undoubtedly be influenced, and some firms will seize the opportunity to leverage technology, offering innovative value propositions and pioneering new business models.

Delving deeper, we explore how corporate law departments are emerging as the true disruptors in the legal market, thanks to advancements in technology. David reveals how these departments are empowered by technology to undertake tasks previously deemed unattainable and how they are able to hire talent at a more junior level, revolutionizing the legal landscape.

Tune in to this inspiring episode as we uncover the remarkable story of David Wang and gain valuable insights into the evolving world of legal innovation and the boundless possibilities that lie ahead.

For more on Cowen Podcasts, Career Coaching, and Leadership Networking Events, please visit www.Cowengroup.com

Did you know Chuck Kellner wanted to be an astronaut when he was seven years old? How did he become one of the consummate established leaders in the eDiscovery and legal technologies world?

In this episode of Careers and the Business of Law, Chuck and I discuss his journey from aspiring astronaut to temp paralegal to Director of Strategic Innovation at one of the world's top five legal technology firms.

We discuss 30 years of change, what matters most, how to achieve success, the past and future workforce, and finally, his favorite band and song. I could have called this episode lessons from an elder statesman.

The Legal Chief Operating Officer is the newest developing role in the law department. Yet, another sign of growing law department maturity and business savvy. And that means the math and economics are changing.

What is a Legal Chief Operating Officer or Director of Legal Business Solutions, and how does a background in legal operations help you achieve this NextGEN career path? 

Greg Kaple shares his career journey into legal operations, business solutions, and his thoughts on the future economics of the corporate law department as well as some Bon Jovi air guitar; "On a steel horse, I ride . Gitty Up, Greg.

In this episode of Careers and the Business of Law - Legal Data Intelligence seriese, David Cowen sits down with Odette Claridge (ProSearch), Tara Lawler (Morgan Lewis), and Virginia Ring (Kilpatrick Townsend) to unpack how Legal Data Intelligence (LDI) is transforming mergers, acquisitions, and divestitures. They share how data governance, AI, and collaboration are reshaping due diligence and deal execution and why frameworks like LDI's toolkit are now must-haves for modern legal teams.

Key Topics Covered:

• How LDI's corporate working group built the first data-driven toolkit for M&A and divestitures.
• Why today's M&A landscape is defined by the 3 Vs of data, volume, variety, and velocity.
• Practical steps for maintaining data integrity and audit trails across multiple corporate entities.
• The new reality: collaboration between legal, IT, privacy, and compliance is non-negotiable.
• How crowdsourcing best practices across firms accelerates learning and innovation.
• What the Architect Program offers for professionals eager to shape the next wave of legal data frameworks.
• A look ahead: AI governance and ethical frameworks as the next frontier for legal data professionals.

🎧 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!

Dera Nevin -Data Policy and Strategy Officer at The Blackstone Group

What can you do in 12 minutes a day? Dera Nevin wrote a book and opened the door to a lifelong dream.

In this conversation, Dera shares her thoughts on how to chunk time into 12-minute increments to accomplish any goal you want to set.

And, of course, we delve into her career journey fron creating the eDiscovery practice at TD Bank to eDiscovery Counsel at Proskauer and her unique and evolving role as the Data Policy and Strategy Officer at The Blackstone Group. 

This is a great listen if you are looking for an inspiring listen on jumpstarting a new initiative or goal.

And here is a link to Dera's book: "The Journey Is The Thing" by Dera Jardine - https://tinyurl.com/3kzkznam

For more on Cowen Podcasts, Career Coaching, and Leadership Networking Events, please visit www.Cowengroup.com

In this episode, Tommie Ferriera - Head of Legal Operations at Cedar, turns the tables on David to find out how he got started, his top tips on networking and meeting new people, and the books that most influenced him.

David provides his top tips on how to get the most out of any conference, including how to approach people, the importance of follow-up, and the benefits of being authentic and building genuine connections.

In the final segment, Tommie asks David to share the books that most influenced him. David lists his top picks, including "Power Failure "—the Story of Leadership and Failure at GE.

You are the average of the 5 people around you. This episode is a must-listen on how to elevate and expand your connections.

For more on Cowen Podcasts, Career Coaching, and Events, please visit www.Cowengroup.com

Jerry Bui, Senior Managing Director of FTI- Social Media as Mentorship and Leading a 3 Generational Workforce.

How do you lead, coach, and impact a 3 generational workforce? Especially now with such an extensive remote workforce and a variety of hybrids? Jerry and I unpack the power of social media as a new form of mentorship.

We also discuss evolving trends in legal technology, the power of AI as an accelerator of careers, and of course, favorite books, podcasts, and what happens after what happens next.

Learn more about Jerry Bui at  https://www.linkedin.com/in/jerrybui/

Thanks for listening!

For more on David Cowen, Cowen Events, and Cowen Executive Coaching, Visit; www.cowengroup.com

Not all law department leaders start out in legal. Sanjay and I discuss his 'Jungle Gym Career Path" as well as ChatGPT, Mentors, Evolving Roles and The Workforce of the Future.

In this episode of Careers and the Business of Law, we have the pleasure of speaking with An Trotter, Director of Legal Operations at Hearst. An Trotter shares her valuable insights on driving innovation in the legal ops department of the future, as well as discussing her innovative new product, Legal Ops in a Box, designed to help jumpstart and advance the legal ops profession. Don't miss out on this informative and insightful interview with An Trotter.

I've had fun and fluid exchanges of ideas with Stephen Goldstein of Squire Patton Boggs for over 20 years. In our chat today we cover the velocity of change in the legal market,  perceived next-GEN killers of revenue, accelerators of innovation and the legal workforce / workplace of the future.

In today's episode of 'Careers in the Business of Law,' David sits down with Bruce Kasanoff, who is one of his core four advisors,  friends, and Ghostwriter to the stars. David and Bruce speak once a week about the marketplace, evolving trends, David's career, and what he should and shouldn't do on social media, a.k.a his brand. So, of course, he is David's first guest.

They talk about the workforce and workplace of the future, the origins of the Cowen Café, leadership, the 3 generational workforces, why David started this podcast, and the impact he hopes it will have on the careers of legal professionals around the world.

This first episode is the "Beginning of the Beginning," and the next rung on David's professional jungle gym. Tune in, gain insights, and hopefully it inspires you to take action.

If you haven't had a virtual cuppa coffee with somebody this week, this podcast episode will inspire you to reach out and connect.

A sneak peak of what's ahead...

In this episode of Careers and the Business of Law, David Cowen sits down with Nathan Reichardt, PwC's Lead Managed Services Director and AI Champion, for a conversation that bridges technology and humanity. They unpack why "observability" isn't just a technical concept, it's the foundation of trust in an age of autonomous agents. From building glass-box systems that make AI accountable to recognizing the invisible pressures on professionals, this discussion explores what it really takes to lead responsibly in the era of AI.

Key Topics Covered:

• Agents aren't magic, you must observe them. Why oversight is essential as AI agents act and learn autonomously.
• From black box to glass box. Transparency, explainability, and compliance as non-negotiable design principles.
• Responsible AI in practice. What observability really means for governance, risk, and trust.
• The rise of new roles. Why "AI Observer" and "Observability Lead" may soon become critical titles inside legal and business ops.
• The human dimension. How leaders can apply observability to people spotting stress, isolation, and burnout before it's too late.
• From pilot to practice. PwC's approach to scaling agentic AI safely through iteration, measurement, and feedback.

🎧 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!

What happens when AI gets faster than your legal team? In this episode, we're pulling back the curtain on the real disruption happening inside law firms, legal departments, and software giants. Microsoft's E.J. Bastien and Relativity's CTO Keith Carlson join David Cowen for a no-holds-barred conversation on AI's impact on legal strategy, workflows, careers and how everything is being redefined.

If you're in legal, tech, ops, or just wondering what your job looks like in 24 months, this is the episode.

Key Topics Covered:

• The AI Wake-Up Call: Why "change resistance" in legal is dead and what's replacing it
• The End of Legal Busywork: How AI is freeing up law firms for high-value thinking
• Billable Hour vs. Business Model: The quiet collapse of traditional legal pricing
• Speed to Insight: Why fast isn't fast enough anymore and how top teams are adapting
• Dark Data, Bright Future: New AI tools surfacing value where no one was looking
• Career Acceleration: Why critical thinkers, puzzle-solvers, and AI-curious pros are thriving
• The AI-Ready Org Chart: What the "firm of the future" looks like (hint: it's flatter and faster)

🎧 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!

What separates a legal department that saves money from one that builds competitive advantage? Two powerhouse CLOs, Rishi Varma (Cargill) and Tim Fraser (Toshiba America) - sit down with David Cowen to unpack the shift from legal risk managers to business growth drivers. If you're a legal leader, strategist, or tech-savvy operator, this is essential listening.

The future isn't coming. It's here. And these leaders are already in it.

Key Topics Covered:

• The AI Dividend: What it is, how to measure it, and why it's your next performance metric
• Data as Infrastructure: Why CLOs are racing to eliminate the "search function" and build a legal "brain"
• OKRs That Matter: How top legal departments align KPIs to business growth, not compliance checklists
• Tech Stack in Action: Inside the tools (Copilot, GenAI) that are driving real productivity gains today
• Talent Evolution: What CLOs actually look for in 2025, critical thinking, adaptability, and strategic fluency
• Cross-Functional Power Moves: Why your next big win requires partnering with your CIO (or CEO)
• From Perfection to Performance: Why "excellence over perfection" is the new rule of law

🎧 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!

Hosted by David Cowen | Presented by Steno

Live at ILTACON 2025, in this candid conversation, Shannon Bales, Litigation Support Senior Manager at Munger, Tolles & Olson, shares how he's preparing his team for the AI-driven future, by turning ticket-takers into consultants. From tools like ChatGPT, Copilot, Harvey, and Claude, to the foundational skills that matter most (language, curiosity, and communication), Shannon talks shop about what it really takes to lead through change in today's legal tech landscape.

If you manage teams, advise on tools, or just want to sharpen your edge, this one's for you.

Key Topics Covered:

• Why Shannon trains his team to be consultants, not just executors
• ChatGPT, Claude, Copilot, Harvey, when to use what, and why
• Why there's no one AI winner (yet) and what due diligence really means
• From curiosity to clarity: why communication is the real AI skill
• How GenAI shifts the legal conversation and why workflows must follow
• Why legal tech leadership today means being agile, patient, and connected
• Shannon's weekend writing practice and why he's documenting GenAI's foundation for legal

This Episode is presented by Steno: Smarter transcripts. Faster delivery. Built for modern legal teams.

🎧 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!

Hosted by David Cowen | Presented by Steno

What does it take to get in "the room where it happens"? Melissa Faragasso, a fifth-year associate at Cleary Gottlieb, didn't wait for permission - she stepped forward, made the ask, and landed a secondment to the firm's innovation team led by Ilona Logvinova.

Live from the floor at ILTACON 2025, in this candid conversation, Melissa shares how a passion for privacy law, a sharp eye on emerging tech, and a dose of courage put her on a path that most associates only dream about. If you're a legal professional curious about GenAI, career growth, or making bold moves, this is your playbook.

Key Topics Covered:

• How Melissa leveraged her privacy expertise to break into legal innovation
• What it really means to "operationalize" GenAI at a top-tier law firm
• The importance of doing it scared and why courage pays off
• How Cleary's acquisition of an AI startup created unexpected opportunities
• Why younger associates might have an edge in emerging tech law
• The value of curiosity, initiative, and asking the right question at the right moment

This Episode is presented by Steno: Smarter transcripts. Faster delivery. Built for modern legal teams.

🎧 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!

Hosted by David Cowen | Presented by Steno

Live at ILTACON 2025, in this wide-ranging conversation with Stephen Dooley, Director of Electronic Discovery and Litigation Support at Sullivan & Cromwell, we dig into the new rhythm of legal tech, how it's evolving, where the real value lives, and why the smartest professionals are not chasing AI, they're designing with it.

From creative use of ChatGPT to legacy-building with AI-generated video, Stephen shares how he's redefining productivity, growth, and human connection at work and at home. If you're feeling overwhelmed by the noise, or wondering how to lead through change, this one will hit home.

Key Topics Covered:

• Why "value" in legal tech is being redefined and what to do about it
• How Sullivan & Cromwell vets new tools, partners, and AI workflows
• The rise of augmented intelligence and how Dooley uses ChatGPT to think, plan, and lead
• Why creativity, not code, is the real differentiator in this AI moment
• What founders, vendors, and buyers must understand about trust and timing
• Lessons from Andrew Sieja, Omar Haroun, and other tech visionaries shaping the next phase
• How to "come together" in a fragmented market and why small pods of connection matter
• A personal look into Stephen's use of AI for family legacy and memorialization

This Episode is presented by Steno: Smarter transcripts. Faster delivery. Built for modern legal teams.

🎧 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!

Hosted by David Cowen | Presented by Steno

Live from the floor at ILTACON 2025, in this rich, retrospective conversation, Phil Bryce, longtime legal Knowledge Management leader and strategist - traces the evolution of legal tech from the dawn of email to today's GenAI disruption. But this episode is about more than just tech. Phil shares hard-earned lessons on connection, courage, and how relationships made 20 years ago still shape his career today.

If you're navigating what's next or building your place in this industry, Phil's story is a masterclass in going far together.

Key Topics Covered:

• What GenAI means now and how it echoes the early days of legal tech
• How Knowledge Management, strategy, and innovation emerged from organized chaos
• The power of connection: how one lunch sparked a 20-year peer network
• Why today's best opportunities aren't in job descriptions, you create them
• "Follow the joy": Phil's framework for building a career worth having
• How courage and curiosity created the career he didn't know he was building
• The future of legal tech leadership and why thinking like a managing partner matters

This Episode is presented by Steno: Smarter transcripts. Faster delivery. Built for modern legal teams.

🎧 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!

Hosted by David Cowen | Presented by Steno

Live at ILTACON 2025, Rachel Shield Williams, Director of Client Intelligence at Sidley Austin, breaks down how the smartest legal teams are using AI, not just to save time, but to build stronger relationships, drive smarter decisions, and unlock entirely new ways of working. From ChatGPT to lakehouses, Rachel shares how the future of legal operations is being shaped by clean data, clear governance, and creative thinking.

This episode is packed with real use cases, sharp insights, and powerful takeaways for anyone working at the intersection of law, data, and strategy.

Key Topics Covered:

• What "client intelligence" really means and why it's a growth engine
• Why governance is the backbone of safe, scalable GenAI
• The difference between data warehouses, lakes, and lakehouses (finally explained)
• How cross-functional teams are reshaping client relationships
• Rachel's ChatGPT workflows - summarizing, strategizing, even grocery shopping
• AI as a leadership tool: how to support your team and stay ahead
• Inclusion, accessibility, and the future of data-driven collaboration

This Episode is presented by Steno: Smarter transcripts. Faster delivery. Built for modern legal teams.

🎧 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!

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

🎧 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!

Hosted by David Cowen | Presented by Steno

Live from ILTACON 2025, this episode features a candid, heart-forward conversation with Melanie Prevost, Senior Director of IT Infrastructure & Technical Support at Vinson & Elkins. Melanie shares how GenAI is empowering neurodiverse professionals, reducing barriers to productivity, and creating real inclusion, not just policy-driven but experience-based.

We dive into how teams are building confidence, collaboration, and creativity through tools like Copilot, Grammarly, and ChatGPT, along with what it means to work across silos, connect with communications teams, and lead from a place of openness and curiosity.

Key Topics Covered:

• How GenAI tools like Copilot, Grammarly, and ChatGPT are leveling the playing field
• Supporting neurodiverse professionals through AI-enabled workflows
• Building psychological safety and confidence across technical teams
• Working across silos: IT + Communications = new power partnerships
• Why accessibility and inclusion need to be built into tech strategy
• What's changing at ILTACON and why it feels different this year
• From recipes to real strategy: how personal AI use is driving workplace adoption

This Episode is presented by Steno: Smarter transcripts. Faster delivery. Built for modern legal teams

🎧 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!

Hosted by David Cowen | Presented by Steno

Live from the floor at ILTACON 2025, this episode dives into the real transformation happening inside law firms and what GenAI has to do with it. Julie Brown, Director of Practice Technology at Vorys, shares why attorneys are finally asking for AI, what it means to build digital agents, and how legal tech professionals have evolved from taskmasters to strategic leaders.

From workflow automation to workforce evolution, Julie breaks down what's changing, what's coming next, and how to stay ahead in a profession that's reinventing itself in real time.

Key Topics Covered:

• How GenAI has flipped the script on legal tech adoption
• Why attorneys are now driving the demand for innovation
• The shift from eDiscovery silos to full-firm strategic impact
• What the rise of digital agents means for tomorrow's workforce
• How legal ops teams are becoming drivers of business value
• Julie's "second career" in agent design, automation, and workflow strategy
• Why human-in-the-loop AI still matters and always will

This Episode is presented by Steno: Smarter transcripts. Faster delivery. Built for modern legal teams.

🎧 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!

What if one judge kills GenAI in court? Former U.S. Magistrate Judge Andrew Peck says it could set legal innovation back a decade.

In this episode, David Cowen and co-host Nicole Giantonio go inside the mind of the "Godfather of eDiscovery" to unpack the real risks, courtroom landmines, and what every lawyer needs to know before using AI in a case. This isn't theory. It's already happening.

What You'll Learn:

• Why one bad GenAI ruling could halt progress for 10 years
• How "hallucinated" case law is already damaging court credibility
• The question no one can agree on: Are AI prompts discoverable?
• What smart firms are doing right now to stay defensible
• Why your judge's tech IQ might matter more than your case facts
• The #1 safeguard Judge Peck says you must have in place today
• What DLA Piper is doing that most law firms still haven't figured out

🎧 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!

Hosted by David Cowen | Presented by Steno

Live from the floor at ILTACON 2025, this episode cuts through the hype and gets into the real AI tools and workflows legal professionals are using right now. Stephanie Clerkin breaks down how GenAI is supercharging court reporting, unlocking billable time, and why "context engineering" may be the most important skill of your career. If you're curious, overloaded, or looking for a competitive edge - you need to hear this!

Key Topics Covered:

• The AI tools shaking up court reporting (Transcript Genius, Verbit AI, and more)
• The security blind spot in transcript workflows and how to close it
• Why "context engineering" is your next competitive advantage
• Agentic workflows explained: what they are and why they matter
• The myth of the disappearing billable hour and what's actually happening
• How Stephanie builds AI muscle on weekends (and why you should too)
• Field-tested career advice for rising legal ops pros

This Episode is presented by Steno: Smarter transcripts. Faster delivery. Built for modern legal teams.

🎧 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!

Will Seaton, Chief Customer Officer at DraftWise and former commercial lead at Palantir sits down with David Cowen to unpack what's really changing at the intersection of AI, contracts, and legal careers. This conversation dives deep into the shift from prompt to context engineering, the rise of roles like forward deployed engineers, and why the future of legal work isn't about replacing lawyers, it's about scaling their judgment. If you're serious about where your team, talent, and tech are headed, this is the episode.

Key Topics Covered:

• What law firms and legal departments can learn from Palantir's forward deployed model
• Why context, not prompts is the real power source behind GenAI in legal workflows
• The new business value of outside counsel: from selling information to selling judgment
• How tools like DraftWise unlock contract data and turn junior lawyers into high performers fast
• The evolution of roles in legal: from lawyers to context engineers, data strategists, and AI copilots
• Augmented intelligence > artificial intelligence: the case for keeping humans in the loop
• What legal AI tells us about the next wave in the demand and flow of talent

People & Ideas We Mentioned:

• Alex Karp, CEO of Palantir – the philosopher-CEO shaping how the world thinks about data and power
• Kyle Bahr from Cleary Gottlieb – sparking smart conversations on context engineering and where legal AI is headed
• Omar Haroun, founder of Eudia (formerly Text IQ) – pushing the boundaries on augmented intelligence in legal
• Song of the Day: "Celebrate" by Jordan Rakei – Will's go-to morning track – Give it a listen

🎧 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!

Bestselling author and "non-obvious" thinker Rohit Bhargava sits down with David Cowen for a high-energy, idea-packed conversation on creativity, persuasion, and building influence in unexpected ways. Drawing from his global bestseller and branding roots at Ogilvy and Leo Burnett, Rohit shares how to spot hidden patterns, spark change inside organizations, and bring others along the journey. If you've ever felt like the only one seeing around corners, this episode is for you.

Key Topics Covered:

• The 4 habits of non-obvious thinkers (and how to build them daily)
• Why ideas alone are worthless and what separates dreamers from doers
• The Einstein lesson: how to find (and be) your "Max Planck"
• Self-serving altruism: the underrated power move in building influence
• How to get others to join your vision without a "hard sell"
• The art of persuasive storytelling from someone trained at Ogilvy and Leo Burnett
• Why getting outside your echo chamber is the secret weapon for innovation

Speacial mention: Rohit's latest bestseller, Non Obvious Thinking, is now available, don't miss 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/

Never eat alone!

Frank Nuzzi, Senior IP Counsel at Siemens, joins David Cowen to unpack the mindset shift every legal professional needs right now. From sandboxing with Microsoft Copilot to pushing the boundaries of AI in legal workflows, this episode dives into how curiosity and experimentation, not perfection are shaping the next generation of legal work. If you're waiting for AI to be flawless before jumping in, you're already behind.

Key Topics Covered:

• Why "don't be cheap on your career" might be the best AI advice you'll hear
• The productivity edge: how Copilot saves time in Outlook and sharpens legal workflows
• Frank's system for learning fast: white papers, eBooks, YouTube, and morning study
• How genAI accelerates legal research and boosts comprehension
• The reality of "time saved" in legal, quality over quantity
• Lessons from DHL's legal playbooks and the power of asking "what if?"
• Why staying curious is the real ROI of AI tools

🎧 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!

Catherine Jopling, General Counsel at MPW Industrial Services, doesn't lead from behind a desk, she builds trust in the field, layer by layer. In this episode, she shares how she leads legal with empathy, curiosity, and proactive strategy in a decentralized, blue-collar business.

Instead of waiting for crises, Catherine gets ahead of them, visiting sites, meeting people where they are, and building systems that make legal a value driver, not a cost center. Whether she's coding a risk registry in SharePoint or talking AI with her executive team, she proves that innovation doesn't require big budgets, just resourcefulness and courage.

🎙 Highlights:

• Leading a lean team of 7 serving 4,000+ across North America
• Legal as a proactive partner, not a reactive fixer
• DIY tech: Building risk tools with ChatGPT + SharePoint
• Trust as the foundation, human connection > automation
• Leadership lessons from books, site visits, and Whitney Houston

💡 Takeaways:

• Build trust before it's needed
• Innovate with what you have
• Legal can and should drive value
• AI is powerful, but relationships are everything

🎯 Try this:
Reconnect with someone in your org before you need to. And take one small step toward building something new, just like Catherine.

🎧 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!

Live from the DHL Legal Innovation Summit, David Cowen sits down with Omar Haroun, co-founder of Eudia, to break down the shift from artificial intelligence to augmented intelligence. Together they unpack what's actually happening in legal innovation: smarter workflows, real cost transformation, and human-machine collaboration at scale. This conversation goes deep from M&A disruption with DHL to the messy middle of change, to the opportunities ahead for those willing to live in the future. If you're trying to figure out how to adapt, evolve, and lead with AI at your side, start here.

What You'll Learn:

• Why AI isn't replacing lawyers but the ones who use it might
• The real reason behind layoffs (hint: it's not just tech, it's operational innovation)
• How DHL and Eudia are unbundling legal services and redefining M&A speed
• What it means to be a Pattern Breaker and why "messy middle" is where the magic happens

Don't wait for the dust to settle.
If you're a seeker, striver, or top guard thinking out loud about AI, talent, and transformation, this one's for you.

🎧Subscribe. Share it with a co-conspirator. And if you're not living in the future yet… what's holding you back?

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

Never eat alone!

What happens when you take legal operations, move it into finance, scale it globally, and build a team of 85 legal professionals inside a Fortune 500? You get Brian Edge's world and it's nothing short of groundbreaking.

Live from the DHL Legal Innovation Summit, David Cowen sits down with Brian, SVP of Legal Franchise & Integrity Shared Services at MasterCard, for a high-energy, human-centered conversation on the next evolution of legal ops. From creating capacity through shared services to layering AI on top of HI (human intelligence), this episode is about unlocking better work, better relationships, and better outcomes at scale.

What You'll Learn:

• Why shared services might be the next big leap beyond traditional legal ops
• How MasterCard scaled legal support globally without outsourcing its soul
• The surprising power of empathy, data, and dashboards in shaping business outcomes
• How AI is enabling, not replacing human brilliance in legal service delivery

This is legal operations V.3, more collaborative, more strategic, more human.

🎧 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!

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

🎧 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 raw and energizing conversation of Careers and The Business of Law from the DHL Legal Innovation Summit, David Cowen sits down with Matthew Smith, Executive Vice President of Business Developmentat Array, to talk about building trust, managing high-performing teams, making the leap into legal from healthcare, and navigating the "middle of the middle" of a career. From the fear of hearing no to the power of shutting up and listening, this is required listening for anyone climbing the jungle gym of leadership.

What You'll Learn:

• How great leaders coach, not micromanage
• Why listening is the most powerful (and overlooked) sales move
• What it really means to lead in the "middle of the middle"
• How values, vision, and relationships shape the second half of a career

Like what you hear?
🎧 Subscribe. Share. Send to someone who needs a jolt of clarity. Because your career's not a ladder, it's a jungle gym. And the climb gets better when we do it together.

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

Never eat alone!

Live from the DHL Legal Innovation Summit in Columbus, David Cowen sits down with Christina Wojcik, Head of Innovation & Partnerships at Pearson Ferdinand, for a high-energy conversation on the future of legal services. Christina breaks down what it means to build a truly tech-first law firm, no associates, no legacy systems, just streamlined, partner-led innovation. From back-office automation to smarter pricing models, this episode explores how law firms can operate leaner, move faster, and deliver more value in a rapidly evolving market.

Key Takeaways:

• Tech-first law firms are rethinking structure, no associates, just distributed, empowered partners
• Automating admin tasks frees up time, margin, and talent for high-value client work
• Clients want to partner on innovation, not just hear about it
• We're in the messy middle of transformation, and the opportunity is wide open

🎧 Tune in, share with your team, and subscribe for more conversations that move legal from now to next.

Because careers aren't ladders, they're jungle gyms.

💡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: The Legal Data Intelligence Series, David Cowen sits down with Richard Pachella, Strategic Alliance Advisor at Epiq, to unpack the seismic shifts happening across legal tech, operations, and talent.

If you're in eDiscovery, legal operations, or just trying to navigate your career in the age of AI, this episode is for you.

🔥 What you'll hear:

• Why the smartest legal pros are leaning into AI now, not later
• How the lines between litigation support, M&A, regulatory, and compliance are blurring fast
• What today's legal departments need: prompt engineers, strategic consultants, and legal technologists who think beyond the silo
• How LDI is transforming from a "think tank" to a "build tank"
• Practical ways to adopt GenAI tools in your day-to-day, starting today

📣 Plus: Rich drops a 60-second insider take on what Epiq is hiring for, and why diverse backgrounds are more valuable than ever.

🎧 If you're serious about staying relevant, expanding your skills, and thinking out loud with the best in the business, press play!

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

Never eat alone!

20 Years. 5 Pivots. 1 Big Bet on GenAI.

🎧 Featuring: Danny Thankachan | Head of Partnerships, CaseGuild

This isn't your average industry chat. This is a high-voltage, real-talk conversation between two longtime insiders, David Cowen and Danny Thankachan on what really matters now in legal innovation, GenAI, and career growth.

📌 Highlights:

• The evolution of eDiscovery from 2004 to today
• Why Legal Data Intelligence (LDI) is more than a buzzword, it's a framework for future-ready work
• Case Guild's bold mission to reinvent internal investigations
• What career reinvention really looks like in the AI age
• And why your job might be disrupted but your career doesn't have to be

🎧 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!

Let's get something straight: the job of General Counsel has left the building. Today's GCs aren't just legal advisors, they're business architects, transformation leaders, and culture drivers. And if your legal team is still playing defense, you're losing ground.

In this episode, Lisa Mather and Tim Fraser, two of the most forward-leaning legal execs in the game, pull back the curtain on how they're redefining the GC role from the center of the business.

What you'll walk away with:

• Why Legal Ops is outgrowing its old box and becoming strategic leadership.
• How the best GCs are operating at "120%" by speaking the language of margin, growth, and product.
• The mindset shift from "risk management" to "value creation" and what that means for your next hire.

🎯 Bonus:
Both Lisa and Tim will be live at the SOLID AI Agentic BootCamp at Microsoft this August and onstage at SOLID New York in September. Want to meet the First 50? Be there. Register here!

This isn't incremental change. It's an entirely new operating model.

Hit play. Share with your team. And start thinking out loud, together.

In this no-BS roundtable, David Cowen sits down with Kevin Cohn - Chief Customer Officer at Brightflag; Tyler Finn, Head of Community & Growth at SpotDraft; and Matthew Wheatley, VP, Client Strategy at Priori to unpack the real state of legal operations, talent, and transformation.

Forget the panel buzzwords. This episode pulls back the curtain on what's actually happening inside high-performing legal teams. What's inside:

• Legal ops has hit a plateau, but careers haven't.
The smartest players are skipping the next rung and stepping into legal strategy, transformation, and C-suite alignment.

• There's no ladder, just a jungle gym.
From executive assistants to legal COOs, this episode is a playbook for navigating ambiguity and turning it into an advantage.

• The real skill gap? It's not tech. It's knowing your value.
Are you a builder, a manager, or a creator? Know your lane, then double down.

This is the episode you forward to your team with one line:
"This is the conversation legal ops needs to hear right now."                                                           

🎧 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!

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.