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Episodes

#66 - So you wanna be a GC?
April 15, 2025

#66 - So you wanna be a GC?

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...

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#65 - What It Really Takes to Be a CLO Today
April 6, 2025

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

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...

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#64 - Why Playing by the Rules Won’t Get You Promoted
March 18, 2025

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

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...

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#63 - Is 2025 The Year Law Firms Finally Transform? - A Conversation with Matt Sunderman, CEO of Harbor Global
March 4, 2025

#63 - Is 2025 The Year Law Firms Finally Transform? - A Conversation …

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...

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#62 - Is Legal Ops Losing Momentum?
Feb. 18, 2025

#62 - Is Legal Ops Losing Momentum?

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 po...

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#61 - If It's Scary, It's Good: How TravelPerk's GC is Reimagining Legal Services
Feb. 4, 2025

#61 - If It's Scary, It's Good: How TravelPerk's GC is Reimagining Le…

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 Fl...

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#60 - No-Redline Revolution: Redefining In-House Legal with Rippling GC Vanessa Wu
Jan. 21, 2025

#60 - No-Redline Revolution: Redefining In-House Legal with Rippling …

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 ...

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#59 - Lawyers vs. the Commute: Making the Office Worth It, with Emily Botello from CBRE
Dec. 31, 2024

#59 - Lawyers vs. the Commute: Making the Office Worth It, with Emily…

“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...

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#58 - Open to Weirdness: Brian Israel on Leading Legal at Anthropic
Dec. 16, 2024

#58 - Open to Weirdness: Brian Israel on Leading Legal at Anthropic

“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 tryin...

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#57 - From Navy Pilot to General Counsel: IPOs and Legal Innovation with Phil Mazzara
Dec. 3, 2024

#57 - From Navy Pilot to General Counsel: IPOs and Legal Innovation w…

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...

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#56 - Ending the Billable Hour: Chris Grant’s Mission to Transform Legal Services
Nov. 19, 2024

#56 - Ending the Billable Hour: Chris Grant’s Mission to Transform Le…

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...

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#55 - Redefining Law Firms: Navigating Change with Legal Visionary Reena SenGupta
Nov. 5, 2024

#55 - Redefining Law Firms: Navigating Change with Legal Visionary Re…

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 ...

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#54 - Navigating Successful Exits: Joe Hyrkin on Leading Issuu to a Nine-Figure Sale
Oct. 22, 2024

#54 - Navigating Successful Exits: Joe Hyrkin on Leading Issuu to a N…

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 publ...

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#53 - Building the Law Firm of the Future: A Conversation with Goodwin’s Leaders
Oct. 8, 2024

#53 - Building the Law Firm of the Future: A Conversation with Goodwi…

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 Part...

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#52 - From Improv to AI: HubSpot CLO Alyssa Harvey Dawson
Sept. 24, 2024

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

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...

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#51 - Mary’s Next Big Move and Life Lessons with Leslie Henthorn from Ironclad
Aug. 13, 2024

#51 - Mary’s Next Big Move and Life Lessons with Leslie Henthorn from…

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...

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#50 - Career Transitions and The Keys to Team Building with Mick Cox from Procore Technologies
Aug. 7, 2024

#50 - Career Transitions and The Keys to Team Building with Mick Cox …

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 Pr...

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#49 - Innovating Legal Ops with Andrew Krug from Twitch
July 24, 2024

#49 - Innovating Legal Ops with Andrew Krug from Twitch

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...

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#48 - CLOC Presidents Roundtable, with Jenn McCarron and Mike Haven
July 3, 2024

#48 - CLOC Presidents Roundtable, with Jenn McCarron and Mike Haven

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...

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#47 - Thinking Upstream: Strategic Legal Leadership with GC Matt Campobasso
June 19, 2024

#47 - Thinking Upstream: Strategic Legal Leadership with GC Matt Camp…

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 Matt Campobasso, the General Counsel and Corpor...

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#46 - Communicate Better at Work with Misha Glouberman, Author, Coach & Advisor
June 5, 2024

#46 - Communicate Better at Work with Misha Glouberman, Author, Coach…

In this episode of Pearls On, Gloves Off , Mary is joined by Misha Glouberman, an acclaimed author, advisor, and coach who excels in the art of effective communication and managing difficult conversations. Together, they expl...

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#45 - Mary's Thoughts on CLOC Global Institute '24
May 24, 2024

#45 - Mary's Thoughts on CLOC Global Institute '24

Special Bonus Episode! Mary goes solo to share her thoughts following CLOC Global Institute (CGI) 2024, answering your burning questions in a special AMA format. Questions: What felt different to you about this year’s CGI? Wh...

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#44 - Change and Innovation in the Age of AI with Ashley John, Head of Legal Ops at Anglo American
May 23, 2024

#44 - Change and Innovation in the Age of AI with Ashley John, Head o…

Note from producer: This is an updated version that addresses an audio issue in the original. Thanks for bearing with us. In this episode of Pearls On, Gloves Off... Mary and Ashley John dig into the dynamic world of legal op...

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#43 - Creating Buy-In and Driving Efficiency with Anna Richards
May 8, 2024

#43 - Creating Buy-In and Driving Efficiency with Anna Richards

In this episode of Pearls On, Gloves Off , Mary O’Carroll sits down with Anna Richards, Director of Global Legal Operations at John Deere. With over 15 years of experience, Anna brings deep insights from companies like Autode...

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