Pearls On, Gloves Off

Years before legal tech hit the mainstream, Jake Saper was already placing bets. As a General Partner at Emergence Capital, Jake helped fund foundational legal tech startups like Ironclad and SimpleLegal—long before most VCs would touch the sector. In this episode, Mary sits down with Jake to unpack his early insights and where he sees the industry heading next. From CLM to AI agents, they explore what’s real, what’s hype, and what buyers and founders should really be paying attention to. Jake isn’t just a savvy investor—he’s a pattern recognizer who sees how AI, pricing models, and workflow orchestration are reshaping not only software but the very structure of legal services. In this episode: Why Legal Was an Early Bet Jake shares why legal’s inefficiencies and high-value work made it an obvious investment target, even before AI and legal ops were mainstream. The Rise (and Risk) of Legal AI From hallucinating tools to real-world adoption challenges, Jake and Mary dissect the current state of AI in legal—and why the billable hour is squarely in the crosshairs. From Tools to Outcomes A candid look at how law firms must overhaul their business models to align with AI-driven efficiencies—and what that means for buyers and vendors alike. “CLM is Dead”? Not So Fast. Jake unpacks why great SaaS isn’t going away anytime soon, despite the buzz around AI agents and “vibe coding.” Hint: trust, workflow, and guarantees still matter. How to Vet Startups in the AI Gold Rush In an era of fast-moving tech and 5-person billion-dollar teams, Jake outlines how to evaluate early-stage legal AI companies: speed, founder authenticity, and value creation over vanity metrics. A Billion-Dollar Perspective Emergence Capital’s latest fund doubles down on the future of B2B SaaS. Jake shares where he’s placing bets—and why job-to-be-done is still the framework that matters most. Whether you're leading a law firm, investing in legal tech, or trying to future-proof your team, this episode is a crash course in thinking strategically about what’s next. Follow Mary on LinkedIn Rate and review on Apple Podcasts

Max Junestrand, CEO of Legora, shares insights on the rapid evolution of legal tech as his startup surged from three founders to nearly 90 employees in two years. He discusses the AI arms race in the legal industry, emphasizing the shift from initial adoption to scaling operations. Junestrand also addresses the concerns around the potential reduction of junior lawyer roles due to AI, while highlighting the importance of trust in tech teams over the tools themselves. He predicts that seamless integration of AI will be crucial for future success in law firms.

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 assistant GC to GC at Dole — and why understanding the business was her secret weapon. Leading Without a Safety Net: The challenges of taking over legal departments where she didn’t have built-in relationships — and how trust became her most critical asset. The Pandemic Lessons: Remote leadership at Panera during COVID and why face-to-face relationships still matter more than ever. Outside Counsel Secrets: What law firms often miss when partnering with in-house teams — and why understanding "what great looks like" is crucial. Public vs. Private Life: How the general counsel’s role shifts dramatically between public and private companies, especially around governance. What Makes the Right Fit: Genevieve shares what she looks for in her next role, and how "fit" and "entrepreneurial spirit" are more important than flashy titles. AI, Innovation, and the New GC: A frank look at how AI is reshaping the future of legal work, and why in-house teams and law firms need to rethink their value propositions — fast. If you're charting your path to GC, leading through change, or just curious about how legal leadership is evolving, this conversation is packed with real talk and hard-won insights. Follow Mary on LinkedIn Rate and review on Apple Podcasts

Anne Kerwin Payne, founder of Kerwin Associates and an expert in legal executive search, discusses the evolving landscape of legal hiring. She reveals that outstanding judgment is the top trait sought by companies in legal leaders. Communication style often trumps resume credentials, and GCs are expected to act like COOs. Anne emphasizes the importance of crafting a compelling career narrative and the role of emotional intelligence in the hiring process. She also navigates the challenges of the current job market, offering insights for aspiring general counsels.

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.

Andy Cooke, General Counsel at TravelPerk, shares his visionary insights on evolving legal services with AI innovations. He discusses the shift from outdated chatbots to advanced AI solutions, emphasizing the importance of customer-centricity in the legal sector. Cooke addresses the need for legal teams to embrace experimentation and diverse perspectives to stay relevant. He also highlights the critical role of data in decision-making and the transformation of legal training, urging future lawyers to adapt to an AI-driven landscape.

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