Pearls On, Gloves Off

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 general counsel or a legal ops pro helping build the next great team, this episode delivers a masterclass in legal leadership hiring. In this episode: The Judgment Factor: Why outstanding judgment—not technical chops—is the #1 trait companies want in legal leaders. The Resume vs. The Room: How communication style and presence carry more weight than you might think—and why the best GCs can command a boardroom with just a few words. Storytelling That Sells: How to craft a career narrative that makes sense, even with lateral moves, gaps, or a long stint at one company. Following the Leader: Why the ability to attract and develop top talent says more about your leadership than your title ever will. The Business-Minded Lawyer: CEOs want legal partners who think like operators. Anne explains why general counsels are increasingly expected to function like COOs. The Reality of the Market: From backdoor references to AI disruption, get a brutally honest take on today’s hiring landscape and what it means for your next move. Whether you're job-hunting, hiring, or just trying to future-proof your career, this conversation is full of insights you can’t afford to miss. Follow Mary on LinkedIn Rate and review on Apple Podcasts

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 past. They talk about building teams during chaos, navigating massive disruption, and why legal expertise alone won’t cut it. In this episode: The CLO Shift: Why being a great lawyer is now table stakes—and how CLOs are expected to operate like full-scale business executives. Burning Buildings & Career Growth: April shares how she built her career by saying yes to hard things, taking on crisis roles, and leading through change. From M&A to Mining: How April’s cross-industry experience—from pineapples to Yankee bonds—gives her a unique edge in global leadership. The 80/20 Rule: April explains why only 20% of her job is “lawyering”—and what the other 80% really looks like. Rethinking Legal Talent: From AI to hybrid work, the next generation won’t learn the way we did—so how do we prepare them to lead? Outside Counsel, Inside Value: What April expects from law firms today, and why relationships matter more than ever. What’s Next for Legal Leadership: Why the CLO role is gaining power in the C-suite—and how legal can stay ahead in a world of nonstop change.  

Kathy Dockry, a seasoned leadership coach and former CEO of a major British energy company, shares insights on what it takes for high-achieving professionals to stand out. She emphasizes that simply doing your job well isn't enough for promotions; mastering the art of influence and storytelling is crucial. Kathy discusses the importance of developmental coaching and feedback, how learning agility predicts success, and offers strategies for self-promotion and articulating value, all aimed at elevating careers in competitive environments.

In this engaging discussion, Matt Sunderman, CEO of Harbor Global and a veteran of the legal industry, shares his insights on law firm transformation. He reveals the spectrum of readiness among firms, from those poised for change to those lagging behind. Matt emphasizes that while technology is a catalyst for transformation, it's not the sole answer. He also dives into market consolidation trends and the implications of KPMG's entry into the U.S. legal market, highlighting the evolving landscape and the urgent need for innovation in legal services.

Frances Pomposo, Senior Director of Legal Technology Solutions at Cisco, offers deep insights into the evolving landscape of legal operations. She and her host discuss the fading role of the 'strategic generalist' and the rise of specialized positions like data analytics. They dive into hiring challenges, debating the pitfalls of flawed recruitment processes. Additionally, the conversation unveils the trend of companies favoring external consultants over in-house teams, and highlights the pressing need for global standards in legal ops roles.

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 dynamics of client expectations and the "convenience economy" Data-driven insights and their role in transforming legal operations Building innovative legal teams and fostering a culture of experimentation Training the next generation of lawyers in an AI-enhanced world Balancing risk and automation in legal operations The importance of customer-centric innovation and listening to "dumb questions" If you enjoyed this conversation, be sure to subscribe to Pearls On, Gloves Off for more candid discussions with leaders shaping the legal and corporate landscape. We’d love to hear your thoughts—connect with us on social media and join the conversation! Goodwin at HumanX  Follow Mary on LinkedIn Rate and review on Apple Podcasts

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 “no-redline” policy for 20,000+ customers—and why sales loves it How fresh thinking on AI (and a PowerPoint from a 9-year-old!) sparked new ways of working Why planned redundancy and constant readiness saved Rippling’s payroll operations Rethinking the legal team’s role as a “future-forward” function rather than a cost center Fostering curiosity and encouraging experimentation—especially when it feels like “cheating” If you enjoyed this conversation, be sure to subscribe to Pearls On, Gloves Off for more candid discussions with leaders shaping the legal and corporate landscape. We’d love to hear your thoughts—connect with us on social media and join the conversation! Goodwin at HumanX Follow Mary on LinkedIn Rate and review on Apple Podcasts

“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 plug-and-play tech and easy reservations to match the convenience of home setups Involving everyone—partners, associates, and naysayers alike—in mapping the path to a better workspace If you enjoyed this conversation, be sure to subscribe to Pearls On, Gloves Off for more candid discussions with leaders shaping the legal and corporate landscape. We’d love to hear your thoughts—connect with us on social media and join the conversation!   Follow Mary on LinkedIn Rate and review on Apple Podcasts  

  “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 perspective on leadership, innovation, and navigating the edge of the possible. Topics covered include: Anthropic’s mission: Building a safer transition to transformative AI and how that shapes the company's operations and values. Legal team culture: What it means to be “appropriately open to weirdness” in service of a larger mission. Hypergrowth dynamics: Lessons from scaling a legal team from one person to 27 in just two years. Front-end legal design: Translating complex legal concepts into actionable advice for fast-moving teams. AI in legal workflows: How Anthropic’s own tool, Claude, has become an integral member of the legal team. Ownership and leadership: Why accountability and agency are critical in a high-stakes environment. Brian’s journey to Anthropic—from NASA to startup land—is as unconventional as his approach to law. Tune in to hear his insights on culture, collaboration, and why the best legal teams are both technically excellent and human-centered. Catch the full conversation now, and don’t miss Brian’s take on how AI is poised to redefine the legal profession. Connect with us and join the conversation: Follow Mary on LinkedIn Rate and review on Apple Podcasts  

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 law firm route and went straight in-house. Prior to joining Astera Labs, he served as General Counsel and Secretary at Innovium, where he oversaw multiple venture financings, negotiated critical commercial agreements, settled bet-the-company litigation, built a robust IP portfolio, and ultimately led the company through its $1.1 billion acquisition by Marvell Technology. At Astera Labs, Phil played a pivotal role in taking the company public in March 2023, a challenging year for capital markets. Under his legal guidance, Astera Labs has been riding the AI wave, focusing on AI infrastructure and experiencing significant growth. In this engaging live conversation, Phil and Mary delve into: ·         The Journey to IPO: Phil shares his experiences taking Astera Labs public in a tough market, the importance of choosing the right outside counsel, and how Goodwin played a crucial role in their successful IPO. ·         AI in Legal Practice: How AI is impacting the legal profession, both within corporate legal departments and in law firms, and the potential future applications of AI in complex legal work. ·         The Evolving Role of General Counsel: Discussing how the general counsel's role has expanded beyond traditional legal services to include compliance, business strategy, and being a key advisor to the executive team. ·         Building Strong Law Firm-Client Relationships: Phil offers advice to law firms on how to better serve their clients, emphasizing the importance of understanding the client's business deeply, being proactive, and building trust. ·         Quality of Legal Work and Service: How to measure and ensure high-quality legal services, the significance of responsiveness, attention to detail, and open communication. ·         Advice for Junior Lawyers: The value of seeking opportunities to engage directly with clients, asking questions to understand their business, and stepping up to deliver work product in front of senior executives. ·         Leadership Lessons from the Navy: Phil reflects on how his experience as a Navy pilot informs his approach to leadership, project management, and the use of checklists to ensure quality and reduce errors. ·         The Future of Legal Practice: A candid discussion on how AI and technological advancements are shaping the legal industry, the enduring importance of judgment and counsel, and the skills lawyers will need to succeed in the future. If you're interested in the intersection of law, technology, and business—or if you're curious about how military experience can translate into corporate leadership—this live episode is a must-listen. Connect with us and join the conversation: Goodwin Exhibit A Follow Mary on LinkedIn Rate and review on Apple Podcasts