#56 - Ending the Billable Hour: Chris Grant’s Mission to Transform Legal Services
Release Date: 11/19/2024
#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
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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_outlineWelcome 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 role at HSBC, he’s been a relentless advocate for efficiency and transformation in legal services. He’s built ecosystems supporting next-generation legal solutions, notably at Barclays Eagle Labs, and has been recognized in the Financial Times Innovative Lawyers Top 10 Entrepreneurs and the Legal 500 GC Power List.
In this episode:
· The Frustration That Fuels Change: Chris shares how his early career disillusionment ignited a passion for legal transformation.
· Is Change Finally Happening? A candid discussion on whether the legal industry is genuinely evolving or just paying lip service.
· The Death of the Billable Hour: Will we ever see it? Chris offers a provocative take on alternative fee arrangements—or as he calls them, Effective Fee Arrangements (EFAs).
· Trust Issues: Delving into the often-unspoken lack of trust between clients and firms, and how it hinders progress.
· Data as the New Gold: How leveraging data can revolutionize legal services, from pricing to service delivery.
· Advice for In-House Teams and Firms: Practical steps both sides can take to build trust, embrace innovation, and deliver real value.
· The Role of Technology: Why AI is more than just a buzzword and how it’s accelerating conversations that were stagnant for decades.
· Future Gazing: Chris’s vision for the next 5-10 years in legal services, and why he believes the time for change is now.
If you’re as passionate about legal transformation as Mary and Chris, or just curious about the seismic shifts shaking up the industry, this episode is a must-listen.
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