Episodes

Mary O’Carroll welcomes Ben Campbell (General Counsel, Deloitte) to unpack how law firms can—and must—learn from consulting and advisory firms. With a career that spans the DOJ, BigLaw, and now a top in‑house role, Ben offers a unique vantage on how governance, compensation, pricing and talent models are evolving. In this episode: Outcome‑based billing: Ben walks through how outcome‑based (versus hourly) billing shifts incentives, aligns with the client, and drives efficiency. Governance at sc...

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 → p...

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‑ha...

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, ...

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-hous...

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 mea...

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...

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 insi...

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 ...

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 ...

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, bu...

In this episode, Mary O’Carroll reunites with Anne Kerwin Payne of Kerwin Associates to dig into one of the most misunderstood yet high-stakes roles in legal: in-house legal operations. If you’re a GC hiring for legal ops—or a candidate trying to land that elusive “head of legal ops” title—this one’s for you. Anne brings decades of legal recruiting insight, a front-row seat to the evolution of the legal ops role, and a refreshingly candid take on what works (and what definitely doesn’t). In th...

When legal ops meets the AI data revolution, what does it actually look like on the ground? In this episode, Mary O’Carroll sits down with Aaron Bromagem, Head of Legal Operations at Snowflake, to talk about what it means to lead legal ops inside one of the top AI and data companies—and why the role today is barely recognizable from just a few years ago. Aaron shares how his team is navigating breakneck change, massive expectations from leadership, and a vendor landscape that’s expanding faste...

Years 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...

Two years ago, Max Junestrand was pitching his legal AI tool in Stockholm. Today, he leads one of the fastest-growing and most talked-about startups in the legal tech space. In this episode, Mary sits down with the CEO of Legora to unpack what’s really happening at the intersection of AI and the legal industry—and what’s coming next. In this episode: Zero to Ninety: How Legora grew from 3 co-founders in a tiny room to nearly 90 employees in under two years—and why growth at that pace is both e...

When Mary O’Carroll arrived at Goodwin, she didn’t expect to find a "General Counsel in Residence" — and certainly not one with the powerhouse career of Genevieve Kelly. In this episode, Mary sits down with Genevieve, whose career includes GC and CLO roles at household names like Panera Bread, Petco, and Dole Food Company. Together, they dive deep into what it really takes to lead legal functions inside massive global organizations — and what Genevieve has learned transitioning between companie...

When your board asks, “Why this GC?”, you'd better have a good answer. That’s where Anne Kerwin Payne comes in. In this episode, Mary O’Carroll sits down with one of the most trusted names in legal executive search. As founder and managing director of Kerwin Associates, Anne has helped place legal and compliance leaders at some of the most innovative companies in the world. She knows what it takes to stand out—and what gets overlooked. They dive deep into what CEOs are really looking for in to...

Producer’s Note: Oops—we hit a tech snag and the original episode got clipped. Here is the full version. Thanks for bearing with us! When April Miller Boise says she runs into burning buildings, she’s not exaggerating—she thrives in transformation. As EVP, Chief Legal Officer, and Corporate Secretary at Intel, April brings a rare blend of legal precision and big-picture business leadership to one of the most complex roles in the C-suite. In this episode, April sits down with Mary to unpack wha...

Today, Mary sits down with Kathy Dockry, a seasoned leadership coach who has spent over 20 years accelerating the success of high-achieving professionals on their journey to executive leadership. Before stepping into the world of coaching, Kathy was a corporate powerhouse herself, rising to become CEO and North American President of a major British energy company. But she didn’t start there—her roots are in law. Having worked as a litigator in two large New York firms and serving as a general co...

Welcome to another episode of Pearls On, Gloves Off with your host, Mary O'Carroll, Chief Operating Officer at Goodwin. In this episode, Mary sits down with Matt Sunderman, CEO of Harbor Global, to explore the current state and future of legal transformation across law firms and corporate legal departments. Matt Sunderman brings over two decades of experience in the legal industry, leading Harbor Global, the newly branded combination of HBR Consulting, LAC Group, Wilson Allen, and others. His un...

When Mary posted a question about the state of legal ops on LinkedIn, she didn't expect to spark such intense debate. But the responses revealed what many have been quietly wondering: has legal operations reached a turning point? In this episode, Mary sits down with Frances Pomposo, Senior Director of Legal Technology Solutions at Cisco, to dig into this thorny question. With her deep experience in tech companies and time on CLOC's board, Frances brings a unique perspective on where legal ops h...

In this episode, Mary O'Carroll sits down with Andy Cooke, General Counsel at TravelPerk, a hyper-growth global tech unicorn providing business travel solutions. Andy, who previously built award-winning teams at Fnatic and Flash Entertainment, shares his innovative approach to legal operations and AI implementation. The conversation explores how legal departments can evolve beyond traditional service models to become true value creators in the age of AI. Topics: Early adoption of AI in legal ope...

In this episode, Mary sits down with Vanessa Wu, the General Counsel at Rippling—a fast-growing platform unifying HR, IT, finance, and more for businesses around the globe. From eliminating contract negotiations by design to harnessing AI for everyday legal work, Vanessa shares how she’s freeing up her team for the most important, high-level tasks. She also opens up about navigating a crisis when Silicon Valley Bank collapsed and Rippling had to hustle a weekend financing—all thanks to smart “No...

“Flexibility is here to stay.” – Emily Botello In this episode, Mary chats with Emily Botello from CBRE about how the legal industry is reinventing its office spaces. From single-size offices and neighborhoods of shared desks to seamless technology and thoughtful change management, Emily shares what’s working, what’s not, and how legal teams are adapting to a world where no two days look the same. Topics: Redefining the office with single-size standards and more collaborative designs Setting “...