Episodes

Mary O’Carroll isn’t experimenting for fun, she’s trying to solve one of legal’s biggest scaling problems: the fact that the profession’s best judgment and hard-earned experience still lives in people’s heads, buried in lapto...

Keir Gumbs, Chief Legal Officer at Edward Jones, isn’t here to maintain the status quo. He joined the largest U.S. financial services firm not to run legal as usual - but to lead a transformation. In this episode, Keir and Ma...

Mary O’Carroll welcomes Stephanie Hamon (Global Head of Legal External Engagement, HSBC) to explore how in‑house legal teams are rethinking their relationships with law firms, vendors, and the broader legal ecosystem. With ex...

Legal recruiters and podcast hosts Genevieve Riccardelli and Jennifer Soltau join Mary to unpack how law-firm hiring is being turned on its head. They run entry-level recruiting at Goodwin and see the shift happening in real ...

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...

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 serv...

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. Toget...

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 l...

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...

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, inno...

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 compa...

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 out...

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, Ma...

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 Algorithmi...

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 Pre...

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 ...

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 ...

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 ...

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 Leg...

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 c...

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 founde...

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 thr...

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 worl...

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 a...