Careers and the Business of Law

Live from ILTACON | Sponsored by Steno What if the next path for a lawyer isn't the traditional path to partnership? Live from ILTACON, David Cowen sits down with Megan McMillin, Legal Innovation Partner at Harvey, to explore one of the most important shifts happening in legal: the emergence of an entirely new career ladder around Legal AI. From Forward Deployed Legal Engineers to Legal Innovation Partners, firms and technology companies are building roles that combine legal expertise, workflow knowledge, technology and client value. The challenge? There is no established playbook yet. In this episode: Why Forward Deployed Legal Engineers are becoming an important new role Why firms need internal experts working alongside vendor engineers The power of combining legal workflow expertise with technical expertise Why successful AI implementation requires understanding the "why," not just the tool What it really means to embed AI talent inside a law firm How Forward Deployed Engineers could progress from building to managing, leading and setting strategy Why Legal AI could create a second career path for lawyers Why firms need to stop treating these roles as "off track" What law schools and firms need to rethink about developing future lawyers Why intellectual curiosity may be one of lawyers' greatest advantages in the AI era Chapters 00:10 | From Cleary to Legal Innovation Partner at Harvey 01:23 | The Rise of the Forward Deployed Legal Engineer 02:10 | Why Firms Need Their Own Embedded AI Expertise 03:18 | Pairing Vendor Engineers With Firm Experts 03:46 | Understanding the Tool, the Workflow and the Why 04:17 | Moving From AI Use Cases to Client Value 05:15 | Why Legal AI Isn't "Choose Your Own Journey" 06:04 | What Embedded AI Talent Really Means 07:09 | Building With the Customer, Not Just for Them 08:21 | The Five-Year Career Path for Forward Deployed Engineers 09:20 | Could Legal AI Become a Second Path to Partnership? 10:16 | Why New Legal AI Roles Command New Compensation 10:46 | There Is No Clear Career Path Yet 11:51 | Stop Trying to Fit New Roles Into Old Structures 12:37 | What Law Schools Need to Rethink 13:41 | The Lawyer's Superpower in the AI Era 14:36 | Why Intellectual Curiosity Matters More Than Ever The Career Signal There is no clear path. It's white space. It's a green field. That's exactly what makes this moment so important. The Legal AI career ladder is being built in real time. You can enter as a builder. Then manage. Then lead. Then set strategy and vision. For lawyers who don't see themselves following the traditional route to partnership, these roles may represent something much bigger than an alternative career. They may be the beginning of an entirely new path. And as Megan puts it, when lawyers and engineers bring their respective expertise together: "The best is yet to come. And we're building it together." Follow SOLID for more conversations with the leaders shaping what comes next in legal: https://solid.legal/ 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! Never eat alone!

Live from ILTACON | Sponsored by Steno Legal technology used to move on annual planning cycles. Now, even 90 days can feel too slow. Live from ILTACON, David Cowen sits down with Damien Riehl, Solutions Champion at Clio, to unpack what happens when the pace of AI development becomes exponential and the traditional boundaries between law, LegalTech and frontier AI begin to disappear. Their conversation moves from the influx of capital and outside talent into legal to the arrival of foundation model companies as new competitors. But the bigger question is what all of this means for lawyers. Could AI reduce the cost of legal work so dramatically that instead of shrinking the market, it unlocks entirely new demand? In this episode: Why legal technology may have moved beyond the 90-day change cycle Where Damien looks to understand what is coming next in AI Why new talent and capital are flooding into legal What happens when frontier AI companies move directly into LegalTech Why data may become the defining advantage for legal technology companies What curiosity, adaptability, resourcefulness and grit mean in an exponential market Why multi-agent AI represents another major shift in how work gets done How AI could dramatically expand access to legal services Why lawyers could become busier because of AI, not in spite of it Chapters 00:10 | Why LegalTech Is on an Exponential Curve 01:18 | From 12-Month Planning to 90-Day Change Cycles 01:42 | Where to Look to Understand What AI Will Do Next 02:39 | The New Talent Entering the Legal Industry 03:21 | Why Capital Is Flooding Into LegalTech 04:27 | When Frontier AI Companies Enter Legal 05:46 | Disruption Disrupting Disruption 06:28 | What Blockbuster, Nokia and Kodak Can Teach Legal 07:16 | The New Build vs. Buy Question 08:10 | You Don't Have to Keep Up With Everything 09:07 | Curiosity, Adaptability, Resourcefulness and Grit 10:19 | What Was Impossible Three Months Ago Is Possible Today 10:35 | The Shift From AI Answers to AI Agents 11:50 | What Happens to Human Capital in an AI Economy? 12:59 | Could AI Actually Increase Demand for Lawyers? 13:38 | The Opportunity to Serve Unmet Legal Needs The Big Idea What if AI doesn't make the legal market smaller? What if it makes the pie dramatically bigger? If AI lowers the cost of legal services, work that was previously too expensive to justify may suddenly become accessible. That creates a very different future for the profession. Instead of lawyers becoming less necessary because of AI, Damien sees the possibility that lawyers become busier than ever because of AI, while serving legal needs that historically went unmet. The challenge isn't knowing everything that's changing. It's staying curious enough to see what just became possible. Follow SOLID for more conversations with the leaders shaping what comes next in legal: https://solid.legal/ 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! Never eat alone!

Live from ILTACON | Sponsored by Steno AI is everywhere in legal. But the biggest change over the last year isn't simply better answers from AI. It's the ability to begin automating the work itself. Live from ILTACON, David Cowen sits down with Chris Emerson, Chief Legal Operations & Innovation Officer, to explore what AI is actually changing inside legal teams, what still hasn't changed, and where the biggest opportunities are emerging. From the growing war for Legal AI talent to turning knowledge trapped inside lawyers' heads into AI-ready workflows, Chris offers a practical look at where legal is heading next, including how his team built an AI-assisted pre-bill review capability in just 33 days. In this episode: Why AI is moving from assistance to actual workflow automation Why adoption remains one of legal's biggest challenges The four traits tomorrow's legal talent needs: curiosity, adaptability, resourcefulness and grit Why leaders should be investing in their top 20% Why the next AI opportunity is getting knowledge out of people's heads and into workflows How AI is shrinking development cycles from months to weeks What leaders should never delegate to AI: strategy, direction and guardrails Chapters 00:10 | AI Everywhere: What Changed in the Last 12 Months? 01:40 | Why Legal's Adoption Problem Hasn't Changed 02:59 | What Leaders Should Look for in Legal AI Talent 04:05 | Curiosity, Resourcefulness, Adaptability & Grit 05:28 | Why Leaders Need to Invest in Their Top 20% 08:30 | Grit, Failure & Why Lawyers Need Rapid Prototypes 10:36 | What Legal AI Still Needs in 2027 12:07 | Where AI Will Create the Next Career Opportunities 13:13 | Turning Legal Knowledge Into AI Playbooks 14:00 | Building AI-Assisted Pre-Bill Review in 33 Days 14:56 | Building an Internal AI Platform Around Firm Data 15:37 | What Should Humans Keep as AI Automates the Work? The Closing Thought "AI is not aware of where we are culturally on the journey." As AI gets better at doing the work, the responsibility for strategy, direction, guardrails and judgment remains human. Follow SOLID for more conversations with the leaders shaping what comes next in legal. https://solid.legal/ 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! Never eat alone!

Most legal teams aren't struggling to find AI tools; they're struggling to implement them in ways that are secure, scalable, and worth the investment. In this episode, David Cowen is joined by Josh Kreamer (Seedless) and Daniel Semelhack (JND) with validation, governance, and practical execution, not experimentation. If you're evaluating AI, leading innovation, or responsible for legal operations, this conversation provides a practical roadmap to move beyond proof of concept and turn AI into measurable business value. Key Topics Covered: Why AI adoption fails, and the four implementation stages every legal team must navigate: scoping, validation, governance, and adoption. The difference between AI adoption and AI utilization, and why only one delivers real ROI. Why testing AI with public datasets is a costly mistake, and how synthetic data produces far more reliable evaluations. How governance accelerates AI adoption by building trust, accountability, and defensible processes instead of slowing innovation. The growing risk of Shadow AI, why it's becoming one of legal's biggest governance challenges, and how organizations can stay ahead of it. Why stakeholder alignment from day one dramatically improves the success rate of enterprise AI initiatives. How practical frameworks, community collaboration, and continuous learning help legal professionals accelerate AI adoption and advance their careers. 🎧 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://solid.legal/podcasts/ Never eat alone!

Lawyers participate in the downside and never the upside, and Jason Barnwell argues that is the single most important thing about to change. David Cowen sits down with Jason, the former Microsoft GM and associate GC who now leads legal at Agiloft, to unpack why the GC role is being rewritten around upside risk, why contract intelligence is becoming business intelligence, and why the legal leaders selling signal back to the enterprise will earn a seat at the CFO's table. Key Topics Covered: Upside risk vs. downside risk: Why legal moves from brake to accelerator and what that changes Probabilistic practice: Accepting outcomes that are less than perfect to open the aperture on what legal can do at scale Contract intelligence as business intelligence: How aggregated contract data becomes a strategic asset The cut line: How budget conversations reward the best stories — and what legal needs to do to stay above the line Storytelling as leadership: Lessons from Microsoft legends Brad Smith, Neil Suggs, and Hossein Nowbar Selling signal back to the enterprise: Packaging contract data into predictive insights that earn legal upside participation Faster deals as legal's superpower: Why predictive contracting becomes the GC's new currency 🎧 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://solid.legal/podcasts/ Never eat alone!

The most honest read on AI adoption in legal might be borrowed from Hemingway: slowly, and then all at once. David Cowen sits down with Adam Becker, director of legal operations at Cockroach Labs, CLOC board member, and one of the architects of the CLOC 101 Academy - to unpack what has actually changed in the last six months, why his team is no longer impressed by AI but expects it, and why the real question is what you are doing with the time AI gives you back. Key Topics Covered: Slowly, then all at once: Why the adoption curve follows the same pattern as every transformational technology before it Capability over efficiency: Why the most important AI gain is being able to do things you literally could not do before The talent surge thesis: Why legal hiring is about to grow, not contract Stratifying the legal stack: NDAs to contract managers, vendor agreements to agents, lawyers to high-stakes work Wordle as a discipline: Why the made bed and the cleaned kitchen are not small things The automated birthday message problem: What we should and should not delegate to our agents The AI dividend list: David's analog notebook of things to do with reclaimed time 🎧 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://solid.legal/podcasts/ Never eat alone!

Legal tech used to live in the trunk - pulled out only when something broke. That era is over. David Cowen sits down with Chad Ergun, whose career has spanned Shearman & Sterling, White & Case, and Gibson Dunn before landing at Womble. Chad unpacks why mid-size firms are now competing with BigLaw, why his refusal to lock into a single AI vendor may be the smartest move in legal IT, and why simulation training is replacing the apprenticeship model. Key Topics Covered: Legal tech's promotion: From the trunk to the passenger seat to the driver's seat The roofing contractor problem: Why the billable hour cannot survive predictable outcomes, timelines, and costs Model hopping as strategy: Why Chad runs six different AI models and refuses vendor lock-in Simulation training for associates: Borrowing from pilots and surgeons to fix the mentorship gap AI doesn't judge you: Why associates ask AI the questions they were too afraid to ask their partners Enterprise data sovereignty: Why running AI on your own tenant is non-negotiable The end of the billable hour by 2027: Chad weighs in on Anthropic GC's bold prediction 🎧 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://solid.legal/podcasts/ Never eat alone!