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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.

business management

All Episodes

42:03

#67 - The Multinational CLO

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/04/29

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 companies,

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47:44

#66 - So you wanna be a GC?

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/04/15

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 today’s

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47:31

#65 - What It Really Takes to Be a CLO Today [Fixed]

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/04/06

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 what it

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47:19

#64 - Why Playing by the Rules Won’t Get You Promoted

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/03/19

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

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49:46

#63 - Is 2025 The Year Law Firms Finally Transform? -...

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/03/04

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 unique

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45:08

#62 - Is Legal Ops Losing Momentum?

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/02/18

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 has

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52:32

#61 - If It's Scary, It's Good: How TravelPerk's GC...

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/02/04

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

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41:29

#60 - No-Redline Revolution: Redefining In-House...

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2025/01/21

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 “North

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46:36

#59 - Lawyers vs. the Commute: Making the Office...

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2024/12/31

“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

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35:43

#58 - Open to Weirdness: Brian Israel on Leading...

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2024/12/16

“Sometimes the right answer for Anthropic would be things that 99% of tech companies wouldn’t even consider. You have to be appropriately open to weirdness—not weirdness for the sake of weirdness, but tied to what we’re trying to achieve in the world.” —Brian Isreal, GC, Anthropic In this episode, Mary sits down with Brian Israel, General Counsel at Anthropic, to explore what it’s like to operate at the legal and cultural frontier of AI. From building a hypergrowth legal team to designing a

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55:03

#57 - From Navy Pilot to General Counsel: IPOs and...

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2024/12/03

This special episode was recorded live at Goodwin's Tech Retreat in San Francisco, where Mary sits down with Phil Mazzara, General Counsel of Astera Labs, to explore the evolving role of the general counsel in today's rapidly changing technological landscape. Phil's journey is nothing short of extraordinary. Before becoming an attorney, he spent over a decade on active duty as a Navy pilot, bringing a unique perspective to the legal field. With a JD/MBA from Stanford, Phil skipped the traditional

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50:09

#56 - Ending the Billable Hour: Chris Grant’s Mission...

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2024/11/19

Welcome to another episode of Pearls On, Gloves Off with your host, Mary O’Carroll, Chief Operating Officer at Goodwin. Today, Mary dives deep with Chris Grant, Head of Legal Market Engagement at HSBC, to unravel the evolving landscape of the legal industry. Chris Grant isn’t your typical legal professional. Frustrated by the glacial pace of change in an industry resistant to innovation, Chris has spent his career challenging the status quo. From his early days in private practice to his current

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45:43

#55 - Redefining Law Firms: Navigating Change with...

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2024/11/05

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 Reena SenGupta, a longtime analyst, writer, consultant, and thought leader in the global legal industry with almost 30 years of experience. Reena’s journey is impressive. She is an entrepreneur and journalist who has developed some of the most influential rankings and programs in the legal world. She was instrumental in creating the Chambers and

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42:06

#54 - Navigating Successful Exits: Joe Hyrkin on...

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2024/10/22

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 Joe Hyrkin, Chief Executive Officer of Issuu, a leading digital publishing platform that’s transformed how content is shared and consumed online. With over 30 years of experience in startup and growth technology leadership across Silicon Valley, New York, Asia, and Europe, Joe brings a wealth of knowledge from early-stage ventures to IPOs and

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42:43

#53 - Building the Law Firm of the Future: A...

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2024/10/08

Welcome to another episode of Pearls On, Gloves Off with your host, Mary O’Carroll, Chief Operating Officer at Goodwin. Today, Mary sits down with Goodwin’s leaders—Anthony McCusker, Chair, and Mark Bettencourt, Managing Partner—for an insightful conversation about the firm’s unique culture, its client-centric approach, and the future of the legal industry. Anthony McCusker is widely recognized as a preeminent adviser in corporate securities and partnership laws, with a primary focus on advising

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42:41

#52 - From Improv to AI: HubSpot CLO Alyssa Harvey...

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2024/09/24

Welcome to another episode of Pearls On, Gloves Off with your host, Mary O’Carroll, Chief Operating Officer at Goodwin. After a brief hiatus, we’re back, and this episode features a fascinating conversation with Alyssa Harvey Dawson, Chief Legal Officer at HubSpot. With over 20 years of experience leading legal teams at major companies like Gusto, Sidewalk Labs, Netflix, and Autodesk, Alyssa shares her insights on navigating AI challenges, the evolving role of legal leadership, and what it takes to

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36:32

#51 - Mary’s Next Big Move and Life Lessons with...

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2024/08/13

Welcome to another episode of “Pearls On, Gloves Off,” where we dive deep into the challenges and innovative strategies within the legal and corporate world. In this episode, we flip the tables. Mary O'Carroll, the powerhouse host you've come to know, becomes the guest as Ironclad's Chief Marketing Officer, Leslie Henthorne, steps in to host. This episode is filled with heartfelt reflections, career insights, and a look at what’s on the horizon for Mary. Mary and Leslie dig into: Mary’s Career

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41:49

#50 - Career Transitions and The Keys to Team...

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2024/08/07

Welcome to another episode of “Pearls On, Gloves Off,” where we dive deep into the challenges and innovative strategies within the legal and corporate world. Today, Mary is joined by Mick Cox, the VP of Legal Operations at Procore Technologies. They dive deep into the evolution of legal operations and the dynamic journey of growing a legal team from scratch. They explore the challenges and triumphs faced while going through career transitions and the strategies for thriving in high-growth

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39:58

#49 - Innovating Legal Ops with Andrew Krug from Twitch

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2024/07/24

Welcome to another episode of “Pearls On, Gloves Off,” where we dive deep into the challenges and innovative strategies within the legal and corporate world. Today, our guest is Andrew Krug, Head of Legal Operations at Twitch, the video live streaming service known for its focus on video game live streaming and esports competitions. Andrew brings a wealth of experience from diverse industries including technology, healthcare, defense, and gaming, making him a unique leader in legal operations.

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56:07

#48 - CLOC Presidents Roundtable, with Jenn McCarron...

Pearls On, Gloves Off: The Legal Innovation Podcast ·

2024/07/03

Welcome to another episode of “Pearls On, Gloves Off,” where we dive deep into the challenges and innovative strategies within the legal and corporate world. Today, we bring together all three past and current CLOC presidents: Jenn McCarron, Mike Haven, and Mary O’Carroll. They discuss everything from Legal Ops, to AI, blockchain, and the meaning of life. In this Episode • The history of legal ops & what is Legal Ops 3.0? • Shifting from financial management to a more integrated, data-driven

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