Pearls On, Gloves Off: The Legal Innovation Podcast

#102 - Inside Crosby: The AI Law Firm Rethinking How Legal Work Gets Done

Mary sits down with Ryan Daniels, Co-Founder and CEO of Crosby, for a rare look inside one of legal tech's most talked-about AI native law firms. They dig into why Ryan b

#101 - Ford's Warning Shot: Adapt or Get Left Behind

Mary sits down with Darth Vaughn, Associate General Counsel and Managing Director of Policy and Legal Ops at Ford Motor Company, for a candid conversation about what it a

#100 - The Future of Legal Is Already Here - A Conversation with CLO Eric Greenberg

Mary sits down with Eric Greenberg, EVP, Chief Legal Officer, and Corporate Secretary at Cox Media Group, for a milestone 100th episode conversation about what it actuall

#99 - Who Is Sandstone? Inside Legal Tech's Most Talked-About Company

Mary sits down with Nick Fleisher, Co-Founder and CEO of Sandstone, to pull back the curtain on legal tech's fastest-rising company. They dig into why great software stil

#98 - Anna Richards

Mary sits down with Anna Richards, Head of Community at Brightflag, to catch up on what's actually happening on the ground in legal ops right now. They dig into the shift

#97 - The Senior Talent Problem Nobody Wants to Talk About

In today's episode, Mary sits down with James O'Dowd, CEO and founder of Patrick Morgan, to explore what legal can learn from the PE and AI disruption already reshaping a

#96 - Curating AI Tools for a Global Law Firm

In today's episode, Mary sits down with Ilona Logvinova, Chief AI Officer at HSF Kramer, to talk about what it actually takes to turn a global law firm into an AI native

#95 - Legal Will Lead The AI Revolution

In today's episode, Mary sits down with Aine Lyons, Senior Vice President & Deputy General Counsel and Chief Strategy Officer at Workday, to talk about what it actually t

#94 - Who Needs Associates? Pierson Ferdinand's Partner Only Model

In today's episode, Mary sits down with Michael Pierson and Joel Ferdinand, Co-Chairmen of Pierson Ferdinand, and Christina Wojcik, their Chief Innovation Officer. Togeth

#93 - Harvey CEO: Individual Productivity Is a Trap

In today's episode, Mary sits down with Winston Weinberg, CEO and Co-Founder of Harvey.ai, to talk about what it actually takes to transform legal - and why buying AI too

#92 - "AI is our Kodak Moment"

In today's episode, Mary sits down with Virginia Briggs, CEO and Managing Partner of MinterEllison, to talk about what real AI transformation actually looks like inside a

#91 - Wordsmith CEO: 70% of Legal Tech Gone by 2027

When Ross McNairn realized his legal career meant reviewing 15,000 documents by hand, he didn't just question the system - he rewrote it. Literally. In this episode, Ma

#90 - Clients "Do Their Own Research." That's A Problem for Law Firms

This episode of Pearls On, Gloves Off is powered by Workday. Learn more at workday.com. In this episode, Mary sits down with Claire Hart, Chief Operating Officer, Chief

#89 - AT&T's New In House Law Firm

In this episode of Pearls On, Gloves Off, Mary sits down with Bill Ryan, Senior Vice President and Chief Compliance Officer at AT&T, and Ava Guo, Assistant Vice President

#88 - Big Law: Record Profits… For Now

In this episode of Pearls On, Gloves Off, Mary sits down with Mike Abbott, Head of the Thomson Reuters Institute, to unpack the paradox: how can firms be thriving on pape

#87 - Updates & Hot Takes with Alex Su

Mary O'Carroll kicks off a new era of Pearls On, Gloves Off - independent, sponsor-curious, and still laser-focused on what's actually changing in legal. Her first guest

#86 - Mary Talks to her Digital Twin

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 ex

#85 - Edward Jones CLO Is Moneyball-ing Legal Risk

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

#84 - Resetting the Relationship with Outside Counsel

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 f

#83 - Recruiting Gen Z Lawyers in a Broken System

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 rec