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PODCAST

Pearls On, Gloves Off: The Legal Innovation Podcast

Join Mary O"Carroll as she sits down with General Counsel, Chief Legal Officers, and industry pioneers to tackle the debates reshaping legal services and technology. Presented by Workday.

business management

All Episodes

55:37

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

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2026/03/31

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, Mary sits down with the Wordsmith ai founder to unpack what happens when a former lawyer turned engineer takes on legal's biggest inefficiencies and why AI is about to redraw the boundaries between in-house teams and law firms. From exploding startup valuations to the rise of "shadow legal," Ross brings a builder's lens to a profession

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55:38

#90 - Clients "Do Their Own Research." That's A...

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2026/03/17

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 Legal Officer, and Board Member at Groq, to talk about what legal leaders should expect in the AI era - from their law firms, their teams, and themselves. With senior leadership roles at Google, Blizzard, and Genies, Claire brings a sharp perspective from the intersection of law, business, and technology. The conversation starts with

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48:05

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

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2026/03/03

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 and Senior Legal Counsel, to talk about leading through the AI inflection point inside a global legal department. As tools evolve monthly and expectations rise, the real differentiator isn't access to technology, it's execution. Bill and Ava share how they're thinking about urgency, culture, ROI, and outside counsel alignment in a

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49:38

#88 - Big Law: Record Profits… For Now

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2026/02/17

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 paper while the ground shifts beneath them? Clients are tightening spend. Work is moving down-market and in-house. AI adoption is accelerating, especially on the client side, yet most of the industry still can't measure ROI beyond "time saved." And the biggest unresolved question hangs over everything: when tech makes legal work faster,

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43:35

#87 - Updates & Hot Takes with Alex Su

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2026/02/03

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 in this new chapter is the person many listeners will recognize instantly: Alex Su. Former litigator, ex-legal tech sales leader, early "legal influencer," and now Chief Revenue Officer at Latitude. This episode is a blunt conversation about the gap between buying innovation and actually using it. Mary and Alex dig into why legal

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28:31

#86 - Mary Talks to her Digital Twin

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2026/01/20

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 laptops, or scattered across years of emails. So in this episode of Pearls On Gloves Off, Mary runs a real test: she trains a digital twin on essentially all of her content (podcasts, talks, blogs, speeches), and then sits down for a conversation with "Digital Mary" to find out

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43:49

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

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2026/01/06

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 Mary talk candidly about what it takes to build a modern legal function inside a legacy institution - and why the traditional law firm model may not survive the decade. Keir brings a rare 360° view of the legal world, with leadership roles at Uber, Broadridge, Covington, and the

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43:55

#84 - Resetting the Relationship with Outside Counsel

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/12/23

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 experience spanning Barclays, Norton Rose Fulbright, and now HSBC, Stephanie brings a uniquely global and pragmatic perspective to legal transformation - from process redesign to AI's impact on delivery models. In this episode: The new panel model: Stephanie explains how HSBC is

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39:39

#83 - Recruiting Gen Z Lawyers in a Broken System

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/12/09

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 time. Their perspective on what students want, what firms are doing, and where this all goes next is honest, practical and very needed. In this episode: OCI is losing its structure. What used to be a predictable, school-run process has fractured. Firms are now interviewing

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48:57

#82 - Deloitte Prices for Outcomes. Law Firms Will Too.

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/11/25

When you hear "law firm," the association is still "time‑based billing, heroic partner hustle, fixed models." But the professional‑services world beyond law has already moved — and moving fast. In this episode of Pearls On, Gloves Off, 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,

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41:20

#81 - The New Structure of AI Powered Law Firms

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/11/11

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 →

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40:33

#80 - Harvey AI's GC: Lawyers Are 20x More...

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/10/28

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

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41:07

#79 - In House Career Growth: Being a Great Lawyer...

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/10/14

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

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47:36

#78 - The Joyful Legal Team

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/09/30

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

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49:48

#77 - Do Law Firms Actually Want Innovation?

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/09/16

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

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01:02:22

#76 - Why “Brilliance” Doesn’t Sell: Rainmaker...

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/09/02

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

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49:29

#75 - Owning the AI Narrative (Before Someone Else Does)

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/08/19

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

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47:24

#74 - From the Ground Up: Building Legal Ops with...

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/08/05

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

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43:57

#73 - Futurist Says: Legal’s Real Risk Is Playing It...

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/07/22

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

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53:44

#72 - Moderna GC’s AI Strategy

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/07/08

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…”

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