#81 - The New Structure of AI Powered Law Firms
Pearls On, Gloves Off
When many law‑ and consulting‑firms ask “Which AI tool do we buy?” they’re missing the bigger shift: the very business model is changing. In this episode, Mary sits down with David Duncan and Tyler Anderson—two long‑time service‑firm innovators—to explore how AI is not just a new tool, but a structural force reshaping professional services: staffing models, pricing, talent, and even the nature of expertise. In this episode: The pyramid unravels: We revisit the traditional "analyst → manager → partner" model and why AI is eroding the base layers. From pyramid to obelisk:...
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#80 - Harvey AI’s GC: Lawyers Are 20x More Efficient... Now What?
Pearls On, Gloves Off
In this episode of Pearls On, Gloves Off, Mary O’Carroll sits down with John LaBarre, General Counsel of Harvey. From Google to Snowflake and now a leader in legal AI, John’s career reflects the tech world’s evolution. Together, they dig into the pivotal moment we’re living through — when generative AI enters the legal profession not as a futuristic idea but as a productivity‑enhancer in real time. In this episode: Why legal is ripe for AI: He explains how the legal profession acts as a “low‑hanging fruit” for generative AI, given its massive volumes of unstructured data...
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#79 - In House Career Growth: Being a Great Lawyer Isn’t Enough
Pearls On, Gloves Off
In this episode, Mary O’Carroll sits down with Rachel St. Peter, General Counsel at Nestlé Health Sciences US, to unpack a bold career move: stepping into legal ops mid-career to grow beyond the “good lawyer” baseline. From leading global transformation out of Switzerland to reshaping her executive presence and business fluency, Rachel explains how ops experience changed her leadership—and her trajectory. They also dig into the future of in-house legal: AI realities, law firm pricing shakeups, and what the next generation of GCs must bring to the table. In this episode: Why being a...
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#78 - The Joyful Legal Team
Pearls On, Gloves Off
In this episode of Pearls On, Gloves Off, Mary sits down with Jacqueline Lee, Senior Vice President and General Counsel at Flynn Group, to unpack what it takes to lead legal, compliance, and risk functions at scale. Flynn is the parent company behind brands like Panera, Taco Bell, Wendy’s, Planet Fitness, and more, with 75,000+ employees across the U.S., Australia, and New Zealand. Jacqueline shares her journey from big law to being unexpectedly tapped for a GC role just a year into her in-house life. Along the way, she reveals what’s really changed (and what hasn’t) in that transition...
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#77 - Do Law Firms Actually Want Innovation?
Pearls On, Gloves Off
Eddie Hartman has been disrupting legal long before it was fashionable. As Co-Founder of LegalZoom and now a Partner & Board Member at Simon-Kucher, he’s worked with everyone from startups to AM Law 100 firms on pricing, innovation, and tech strategy. In this episode, Mary sits down with Eddie to talk about the legal industry’s industry’s uneasy relationship with change. From AI hype to the stubborn grip of the billable hour, they unpack why so many “innovations” fail, what clients actually mean when they ask about tech, and how law firms can evolve without losing their...
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#76 - Why “Brilliance” Doesn’t Sell: Rainmaker Strategies for 2025
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When it comes to business development in professional services, Matt Dixon has spent decades decoding what actually works—and what doesn't. As a bestselling author and Founding Partner at DCM Insights, he’s reshaped how companies think about sales. Now, with his new book The Activator Advantage, Matt turns his focus to the world of law, consulting, and other relationship-driven fields, where selling is often taboo—but still essential. In this episode, Mary sits down with Matt to unpack what top-performing partners do differently—and why it has nothing to do with cocktail parties or...
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#75 - Owning the AI Narrative (Before Someone Else Does)
Pearls On, Gloves Off
When it comes to legal innovation, Jim Delkousis doesn’t just have a front-row seat—he’s one of the architects of change. As Founder and CEO of PERSUIT, Jim has spent almost a decade transforming how legal departments buy outside counsel services. With billions in legal work processed through the platform, he offers a rare, data-rich perspective on the shift from opaque hourly billing to value-driven, transparent legal spend. In this episode, Mary reconnects with Jim for a wide-ranging and insightful conversation about what’s changing in legal procurement, why, and what it means for...
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#74 - From the Ground Up: Building Legal Ops with Sean Houston
Pearls On, Gloves Off
When you think of legal ops at a global company like Heineken, you might not picture a former sports broadcaster leading the charge. But that's exactly Sean Houston’s path—and it’s given him a unique edge. In this episode, Mary sits down with Sean, Heineken’s Head of Legal Operations, to unpack how he built the function from scratch. From vendor-side lessons to internal change management, Sean shares sharp, actionable insights on making legal ops work in a complex, global environment. In this episode: Unlikely Origins: How Sean went from a mic in hand as a sports broadcaster to a key...
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#73 - Futurist Says: Legal’s Real Risk Is Playing It Safe
Pearls On, Gloves Off
In this episode, Mary sits down with futurist and bestselling author Mike Walsh to explore what happens when a tradition-bound industry like law collides with generative AI. Walsh, CEO of Tomorrow and author of The Algorithmic Leader, has advised the world's biggest companies on digital transformation—and he believes legal is facing a moment of radical reinvention. Together, they pull no punches on what the next decade will bring, why legal might be the most vulnerable industry of all, and how leaders can stop dabbling in AI and start building the future. In this episode: The Law of (AI)...
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#72 - Moderna GC’s AI Strategy
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What does it look like when a general counsel doesn’t just adopt AI—but rewires her entire legal function around it? In this episode, Mary O’Carroll sits down with Shannon Thyme Klinger, Chief Legal Officer at Moderna and President of Moderna Charitable Foundation. Named by the Financial Times as one of the most innovative GCs of the past two decades, Shannon is reshaping what it means to lead a legal team—and a profession—through profound change. In this episode: “AI won’t replace lawyers, but…” Shannon lays out her bold vision: why lawyers who don’t harness AI may get...
info_outlineYears before legal tech hit the mainstream, Jake Saper was already placing bets. As a General Partner at Emergence Capital, Jake helped fund foundational legal tech startups like Ironclad and SimpleLegal—long before most VCs would touch the sector.
In this episode, Mary sits down with Jake to unpack his early insights and where he sees the industry heading next. From CLM to AI agents, they explore what’s real, what’s hype, and what buyers and founders should really be paying attention to.
Jake isn’t just a savvy investor—he’s a pattern recognizer who sees how AI, pricing models, and workflow orchestration are reshaping not only software but the very structure of legal services.
In this episode:
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Why Legal Was an Early Bet
Jake shares why legal’s inefficiencies and high-value work made it an obvious investment target, even before AI and legal ops were mainstream.
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The Rise (and Risk) of Legal AI
From hallucinating tools to real-world adoption challenges, Jake and Mary dissect the current state of AI in legal—and why the billable hour is squarely in the crosshairs.
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From Tools to Outcomes
A candid look at how law firms must overhaul their business models to align with AI-driven efficiencies—and what that means for buyers and vendors alike.
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“CLM is Dead”? Not So Fast.
Jake unpacks why great SaaS isn’t going away anytime soon, despite the buzz around AI agents and “vibe coding.” Hint: trust, workflow, and guarantees still matter.
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How to Vet Startups in the AI Gold Rush
In an era of fast-moving tech and 5-person billion-dollar teams, Jake outlines how to evaluate early-stage legal AI companies: speed, founder authenticity, and value creation over vanity metrics.
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A Billion-Dollar Perspective
Emergence Capital’s latest fund doubles down on the future of B2B SaaS. Jake shares where he’s placing bets—and why job-to-be-done is still the framework that matters most.
Whether you're leading a law firm, investing in legal tech, or trying to future-proof your team, this episode is a crash course in thinking strategically about what’s next.