#38 - Legal Ops at Expedia: A Conversation with Mike Russell, Head of Global Legal Operations at Expedia Group
Release Date: 02/28/2024
#67 - The Multinational CLO
Pearls On, Gloves Off
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, cultures, and leadership roles. In this episode: Homegrown GC: How Genevieve rose from...
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#66 - So you wanna be a GC?
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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 legal hires, and why pedigree alone won’t cut it. Whether you’re an aspiring...
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#65 - What It Really Takes to Be a CLO Today
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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 really takes to become a CLO today—and why it’s nothing like the GC roles of the...
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#64 - Why Playing by the Rules Won’t Get You Promoted
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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 counsel before transitioning into operational leadership, Kathy understands firsthand the...
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#63 - Is 2025 The Year Law Firms Finally Transform? - A Conversation with Matt Sunderman, CEO of Harbor Global
Pearls On, Gloves Off
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 position at the intersection of law firms, corporate legal departments, and technology...
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#62 - Is Legal Ops Losing Momentum?
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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 been—and where it might be heading. In this episode: ...
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#61 - If It's Scary, It's Good: How TravelPerk's GC is Reimagining Legal Services
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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 operations and the evolution from "dumb chatbots" to sophisticated AI solutions The changing...
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#60 - No-Redline Revolution: Redefining In-House Legal with Rippling GC Vanessa Wu
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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 Star” planning long before the alarm bells rang. Topics: Maintaining a...
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#59 - Lawyers vs. the Commute: Making the Office Worth It, with Emily Botello from CBRE
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“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 “anchor” days and neighborhoods to encourage in-person connections Ensuring...
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#58 - Open to Weirdness: Brian Israel on Leading Legal at Anthropic
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“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 legal “front end” that prioritizes user experience, Brian shares his...
info_outlineIn 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.
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The Journey Through Legal Tech Evolution: Discover Mike's early experiences in the 90s with the advent of internet technology in law firms, shaping his profound understanding of legal operations, time billing, and the billable hour concept.
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Legal Ops and Legal Tech Synergy: Mike discusses the parallel growth of legal operations and technology over the past decade, highlighting the shift from a focus on profitability to efficiency and the reduction of waste within legal processes.
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A Guide to Metrics and KPIs: Co-authoring a book on metrics and KPIs, Mike offers practical advice on capturing data, presenting it effectively to General Counsels, and making data actionable through visual presentation.
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Performance Indicators and Efficiency: Emphasizing the importance of spend metrics, performance tracking, and the analysis of work origin and complexity, Mike shares how these indicators can offer deep insights into legal operations efficiency.
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Simplifying Technology in Data Analysis: Advocating for simplicity in technological systems, Mike discusses the significance of tailoring data presentation to the audience's needs and the potential of natural language query tools to revolutionize data accessibility.
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Starting Your Metrics Journey: For those embarking on their journey with KPIs and metrics, Mike recommends leveraging community resources, understanding organizational needs, and fostering cross-departmental relationships to highlight the value of legal operations.
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