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

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

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💡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