Episodes

“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 lega...

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 traditiona...

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...

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...

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 an...

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 advisin...

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...

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 ...

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 enviro...

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. ...

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 a...

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 Corporate Secretary at Enfusion, a fintech company revolutionizing investment management through its cutting-edge software solutions. About the Guest Matt oversees the legal function at Enfusion, ensuring the company’s interests are protected while managing legal risks effectivel...

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 explore the intricate dance between analytic thinking and emotional understanding in the workplace. Mary and Misha delve into: • Effective Communication: Misha underscores the critical importance of balancing analytical and emotional aspects in communications, focusing on real-...

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? What are your thoughts on where we are with AI? How can there be so many CLMs? Can you recap what you said in your speaking sessions? What comes next? Mary dives into the unique aspects of this year's event, the evolving role of AI in legal operations, and the market d...

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 operations. Ashley, the Head of Legal Operations at Anglo American, brings a unique perspective from his background in mining and geology to his strategic role in a global mining giant. Key Highlights: Introduction to Ashley John: Transitioning from geology to legal ops. Es...

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 Autodesk, Zendesk, and Micron Technology.Mary and Anna dig into: Transitioning to John Deere: Anna details her onboarding journey, where Deere laid the groundwork by first understanding the role of legal operations and investing in its success. Unique Challenges: As one of the fe...

In this episode of "Pearls On, Gloves Off," Mary sits down with Dawn Hinz, legal operations leader at Avery Dennison. Together, they dive into the nuances of leading and transforming the legal ops landscape. In The Episode: Exploring Strategy and Improvement: Dawn’s role at Avery Dennison: strategy development, process enhancement, and resource optimization. She shares her methodologies in change management and the hurdles faced during large-scale tech implementations. Cultivating Success: Th...

In this episode of Pearls On, Gloves Off, Mary O'Carroll welcomes the formidable Charlene Barone, currently steering the ship as the Director of Legal Operations at the New York Times. Charlene, with her rich history traversing from contracts manager to legal ops leader, brings a wealth of knowledge from both the startup world and the franchise legal landscape of Orange Theory Fitness. A Tale of Two Worlds: Mary and Charlene explore the contrasts and challenges f@aced in the legal departments o...

In this episode of Pearls On, Gloves Off, Mary O’Carroll sits down with Chris Clearfield, a true trailblazer in the world of leadership and management. As the CEO of Clearfield Group and the co-author of “Meltdown,” Chris brings a fresh take on how to lead through the chaos and complexity of today’s business landscape. Change Leadership, Not Management: Mary and Chris dig into why “change management” just doesn’t cut it. Chris suggests we need to shift our focus to “change leadership” - guiding...

In this solo episode, Mary O’Carroll shares her insights on Contract Lifecycle Management (CLM). She explores: The Challenges of Contracts: Overview of common issues in contract processes and the potential for improvement. Ownership of CLM: Advocates for General Counsel to lead CLM processes, highlighting the strategic value of contracts data. Evolution of CLM Technology: From basic database systems to modern, comprehensive CLM solutions that facilitate collaboration and integration. Selecti...

In this compelling episode of "Pearls On, Gloves Off," Mary hosts Mike Russell, a seasoned expert in legal operations and legal technology with a career spanning over three decades. From the dawn of internet technology in law firms to the current emphasis on efficiency and innovation, Mike shares invaluable insights into the evolution of legal ops and tech. The Journey Through Legal Tech Evolution: Discover Mike's early experiences in the 90s with the advent of internet technology in law firms,...

In this episode of Pearls On, Gloves Off Episode: Leadership and Learning with Darek Kochman Mary O'Carroll talks with Darek Kochman, Director of Global Legal Operations at Kimberly-Clark Corp, about his journey from the military to leading global operations. Here’s what they cover: Diverse Background: Darek's path through the military, KPMG, and into legal operations showcases a non-traditional approach to leadership. Key Leadership Imperatives: Darek outlines his leadership principles: Cult...

In this episode of Pearls On, Gloves Off: Join Mary O'Carroll in a riveting conversation with Andrew Perlman, a visionary in law and technology. As the Dean and Professor of Law at Suffolk University Law School, Perlman is pioneering the future of legal innovation. AI's Legal Landscape: Perlman takes us through the evolution of AI in law, forecasting its transformative impact while addressing confidentiality concerns. Realistic Expectations for AI Tools: Dive into the practicality of AI – eff...

In this episode of Pearls On, Gloves Off Mary sits down with her own own executive coach, Kim Kokoska, for a deep dive into the psychology of self-perception and empowerment. Listen in as they unpack some transformative ideas: Victim vs. Observer Mindsets: dissecting the 'victim triangle', featuring the roles of victim, persecutor, and rescuer. They explore how we often oscillate between these roles in interactions. Embracing the Empowerment Triangle: Transitioning from victimhood, they introd...