#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?
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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
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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_outlineIn 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 — especially around how legal advice must shift to be more strategic, practical, and business-aligned.
In this conversation, you’ll learn:
- How to translate your legal skills for non-lawyer clients. Jacqueline stresses the importance of tailoring advice to how business leaders think and act — not how lawyers talk.
- Why “perfect information” is a myth in-house. You’ll hear how GCs must balance risk, ambiguity, and the need to move fast.
- How to lead through crisis and uncertainty. Jacqueline’s leadership during the pandemic reveals lessons in transparency, empathy, and restoring a feeling of control.
- How to demonstrate real value to the business. She explains her shift from narrative legal reports to visual dashboards, metrics tied to core business KPIs, and proactive reporting.
- The case for in-house litigation. Flynn handles much of its litigation internally; Jacqueline explains how they pick which matters to pursue internally vs. outsource — and why she still loves law.
- How to recruit, grow, and scale a legal team. We dig into her hiring philosophy, aligning on values, and the challenges of hybrid teams.
- Pricing and partnership with outside counsel. Jacqueline critiques the inefficiencies of hourly billing and shares how value-based arrangements can align incentives and build trust.
If you’re an aspirational in-house counsel or a legal leader grappling with how to prove impact, this episode is packed with insights you can start applying now.
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