Pearls On, Gloves Off

Eddie Hartman has been disrupting legal long before it was fashionable. As Co-Founder of LegalZoom and now a Partner & Board Member at Simon-Kucher, he’s worked with everyone from startups to AM Law 100 firms on pricing, innovation, and tech strategy.  In this episode, Mary sits down with Eddie to talk about the legal industry’s industry’s uneasy relationship with change. From AI hype to the stubborn grip of the billable hour, they unpack why so many “innovations” fail, what clients actually mean when they ask about tech, and how law firms can evolve without losing their identity. In this episode: LegalZoom’s Early Lessons: Why paralegals—not lawyers—were the first adopters, and what that reveals about confidence, adoption, and who really drives change. AI’s False Start: The real reason 95% of AI initiatives fail—and why law firms may never fully embrace the efficiency it offers. Innovation vs Incentives: How law firms unintentionally kneecap their own innovation efforts—and what spinning off “tech incubators” says about the business model. What Pricing Really Signals: Why clients don’t necessarily want cheaper—they want predictable, credible, and justified. And how fees send louder messages than firms realize. The Human Roadblock: From cultural protectionism to career incentives, why most resistance to change isn’t technological—it’s personal. If you’re tired of the hype cycle and looking for a sharp, grounded view of where legal innovation actually stands, this conversation delivers. Follow Mary on LinkedIn Rate and review on Apple Podcasts  

When it comes to business development in professional services, Matt Dixon has spent decades decoding what actually works—and what doesn't. As a bestselling author and Founding Partner at DCM Insights, he’s reshaped how companies think about sales. Now, with his new book The Activator Advantage, Matt turns his focus to the world of law, consulting, and other relationship-driven fields, where selling is often taboo—but still essential. In this episode, Mary sits down with Matt to unpack what top-performing partners do differently—and why it has nothing to do with cocktail parties or golf outings. Based on a global study of 3,500 partners, his research reveals a powerful new playbook for growing client relationships that’s grounded in thoughtfulness, generosity, and strategic action. In this episode: The Five Partner Personas: From the Expert to the Confidant to the Activator, why most partners fall into outdated models—and what separates top performers. Why “Sales” Is a Dirty Word: Matt shares his story of getting cut off mid-presentation by a managing partner—and what it taught him about the legal mindset. What Clients Really Want: A direct line from clients themselves—what they wish partners would do more often, and why “waiting for the phone to ring” doesn’t cut it anymore. The Power of Proactive Help: Why offering value before the invoice makes Activators so successful—and how it builds lasting loyalty. It’s Not About Personality: Whether you're introverted or hate networking, this isn’t about becoming someone else—it’s about small shifts that make a big difference. The Role of the Firm: How BD and marketing teams can become activator enablers—and why leadership buy-in is key to scaling the model. If you’ve ever felt allergic to the idea of selling—or struggled to connect with clients beyond the brief—this episode offers a fresh, practical, and inspiring blueprint for doing BD differently. Get exclusive legal insights on healthcare’s latest – only with Goodwin at HLTH. Follow Mary on LinkedIn Rate and review on Apple Podcasts

When it comes to legal innovation, Jim Delkousis doesn’t just have a front-row seat—he’s one of the architects of change. As Founder and CEO of PERSUIT, Jim has spent almost a decade transforming how legal departments buy outside counsel services. With billions in legal work processed through the platform, he offers a rare, data-rich perspective on the shift from opaque hourly billing to value-driven, transparent legal spend. In this episode, Mary reconnects with Jim for a wide-ranging and insightful conversation about what’s changing in legal procurement, why, and what it means for firms and clients alike. In this episode: The Death of the Billable Hour? How AI and data are eroding time as the currency of legal value—and what might replace it. The Power of Price Transparency: Why over 80% of matters on PERSUIT now use alternative fee arrangements, and what that says about the future of legal pricing. Reverse Auctions, Explained: The most controversial feature in PERSUIT—and why it’s not necessarily a race to the bottom. When the Lowest Bid Doesn’t Win: Jim shares the data behind client decision-making A GC’s New Mandate: From cost center to value driver, what legal leaders need to prove to their CEOs—and how tech is helping them do it. If you’ve ever questioned the logic of hourly billing—or wondered how to move beyond it—this episode will challenge your assumptions and offer a roadmap forward. Follow Mary on LinkedIn Rate and review on Apple Podcasts

When you think of legal ops at a global company like Heineken, you might not picture a former sports broadcaster leading the charge. But that's exactly Sean Houston’s path—and it’s given him a unique edge. In this episode, Mary sits down with Sean, Heineken’s Head of Legal Operations, to unpack how he built the function from scratch. From vendor-side lessons to internal change management, Sean shares sharp, actionable insights on making legal ops work in a complex, global environment. In this episode: Unlikely Origins: How Sean went from a mic in hand as a sports broadcaster to a key voice in legal transformation. When to Say No: Learning the hard way how to push back and prioritize when everything feels like a good idea. From Vendor to Buyer: Why experience on the vendor side gives you X-ray vision into what makes tech rollouts succeed—or stall. AI Reality Check: No hype, just practical: How Sean is introducing AI across the team through Copilot and internal bots, focusing on comfort and adoption over flash. Europe Rising: Why legal ops in Europe is no longer in catch-up mode—and how it’s finding its own rhythm. Hiring Smart: Why the best legal ops talent might come from inside your own company—and what Sean looks for when building his team. If you're scaling legal ops, wrestling with tech priorities, or just curious how to make meaningful change in a global org, this episode is packed with insight. Sean brings clarity, candor, and a practical mindset to the big questions shaping the future of legal. Follow Mary on LinkedIn Rate and review on Apple Podcasts

In this episode, Mary sits down with futurist and bestselling author Mike Walsh to explore what happens when a tradition-bound industry like law collides with generative AI. Walsh, CEO of Tomorrow and author of The Algorithmic Leader, has advised the world's biggest companies on digital transformation—and he believes legal is facing a moment of radical reinvention. Together, they pull no punches on what the next decade will bring, why legal might be the most vulnerable industry of all, and how leaders can stop dabbling in AI and start building the future. In this episode: The Law of (AI) Acceleration: Why COVID-19 was just the warm-up, and how AI is catalyzing changes that would’ve taken another decade to materialize. The End of the Billable Hour? Walsh and Mary go deep on how AI threatens professional services’ most sacred cow—and what firms must do to stay profitable. The Risk of Inaction: Playing it safe is no longer the safe move. Legal leaders who cling to the past may be making the riskiest bet of all. The Fifth Industrial Revolution: AI isn’t just another tech tool—it’s the next electricity. What that means for organizations, talent, and operating models. Smart, Lazy People Wanted: Why the most valuable hires today are the ones who automate themselves out of a job. Legal as a Living System: A bold new vision for in-house teams—dynamic, embedded, and redefining how companies manage risk in real-time. If you’re wondering what it really means to future-proof a legal org—or whether that concept is a myth to begin with—this episode will give you a front-row seat to the disruption already underway. Follow Mary on LinkedIn Rate and review on Apple Podcasts

What does it look like when a general counsel doesn’t just adopt AI—but rewires her entire legal function around it? In this episode, Mary O’Carroll sits down with Shannon Thyme Klinger, Chief Legal Officer at Moderna and President of Moderna Charitable Foundation. Named by the Financial Times as one of the most innovative GCs of the past two decades, Shannon is reshaping what it means to lead a legal team—and a profession—through profound change. In this episode: “AI won’t replace lawyers, but…” Shannon lays out her bold vision: why lawyers who don’t harness AI may get left behind—and how her team at Moderna is using GPTs, reasoning models, and agents to transform everything from contracts to compliance. From Skepticism to Buy-In: How Shannon got a room full of reluctant legal leaders to see AI’s potential—by showing, not telling. The Self-Service Revolution: Why Moderna’s business teams now use AI-powered contract tools to answer 90% of their questions—freeing legal to focus on higher-value work. Fearless Experimentation: The mindset shift that changed everything: fail fast, learn faster. Beyond Legal: Why Shannon sees legal ops as a strategic engine, not a back-office function—and how her team is training other departments to work smarter with AI. The Big Picture: Shannon’s take on the future of legal—what’s at risk, what needs to change, and why it’s time for GCs and law firms to rewrite the playbook. If you’ve ever wondered what real legal transformation looks like—led from the top, grounded in purpose, and driven by tech—this conversation is your blueprint. Follow Mary on LinkedIn Rate and review on Apple Podcasts

In this episode, Mary O’Carroll reunites with Anne Kerwin Payne of Kerwin Associates to dig into one of the most misunderstood yet high-stakes roles in legal: in-house legal operations. If you’re a GC hiring for legal ops—or a candidate trying to land that elusive “head of legal ops” title—this one’s for you. Anne brings decades of legal recruiting insight, a front-row seat to the evolution of the legal ops role, and a refreshingly candid take on what works (and what definitely doesn’t). In this episode: What Even Is This Job? Why the role of legal ops is still hard to define—and how that creates hiring gridlock on both sides. The Strategic Leap: What it really takes to go from #2 legal ops to department lead—and why most people underestimate the soft skills required. Hiring Mistakes GCs Make: From hiring too junior to skipping overqualified candidates out of fear, Anne shares the missteps she sees most often. The Resume Trap: How over-engineered CVs, AI-generated cover letters, and fuzzy job histories are derailing great candidates. Title Chasers vs. Builders: A frank conversation about compensation, career moves, and the difference between a “job” mindset and a long-term career play. The GC-Legal Ops Chemistry Test: Why your first hire in legal ops needs to be more than a taskmaster—and how to find a true partner. Whether you're trying to land your first legal ops role, move up the ladder, or finally hire the right partner for your legal team—this episode lays it all out. Mary and Anne cut through the noise with practical guidance and stories that’ll help you make smarter moves in a role that’s only getting more critical. Follow Mary on LinkedIn Rate and review on Apple Podcasts

When legal ops meets the AI data revolution, what does it actually look like on the ground? In this episode, Mary O’Carroll sits down with Aaron Bromagem, Head of Legal Operations at Snowflake, to talk about what it means to lead legal ops inside one of the top AI and data companies—and why the role today is barely recognizable from just a few years ago. Aaron shares how his team is navigating breakneck change, massive expectations from leadership, and a vendor landscape that’s expanding faster than anyone can track. If you’ve ever felt like your strategy gets outdated before you even finish writing it down, this one’s for you. In this episode: Navigating Uncertainty: Aaron opens up about what it’s like to lead in an environment where priorities shift every quarter—and why nimbleness beats planning. GCs as Technologists: The modern general counsel is demanding more data, faster delivery, and deeper insights. Here’s what that means for legal ops. The Rise of the Legal Data Model: How Snowflake built a system to turn legal operations data into reliable enterprise intelligence—and why it’s powering product features now. Prompt Engineering vs. Agent Workflows: As AI evolves, are we moving from writing prompts to building complex legal workflows powered by agents? The Vendor Maze: Why every legal tech vendor says the same thing—and how Aaron separates the useful from the fluff. A New Profile for Legal Ops: Technical backgrounds, data fluency, and an operations-first mindset—Aaron and Mary discuss how the ideal candidate is changing. If you’re in legal ops and feel like you’re barely keeping up with the pace of change, you’re not alone. But as Aaron shows, with the right mindset and tools, there’s huge opportunity in the chaos. Follow Mary on LinkedIn Rate and review on Apple Podcasts

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

Two years ago, Max Junestrand was pitching his legal AI tool in Stockholm. Today, he leads one of the fastest-growing and most talked-about startups in the legal tech space. In this episode, Mary sits down with the CEO of Legora to unpack what’s really happening at the intersection of AI and the legal industry—and what’s coming next. In this episode: Zero to Ninety: How Legora grew from 3 co-founders in a tiny room to nearly 90 employees in under two years—and why growth at that pace is both exhilarating and challenging. The AI Arms Race: Why Max thinks we're past the “zero to one” moment in legal AI, and what “ten to one hundred” really looks like. Enterprise First: Legora's bold move to build for big firms from day one—and how they won over skeptical managing partners and corporate buyers. The ROI Reckoning: As CFOs tighten the purse strings in 2025, Max breaks down how law firms are thinking about pilots, platform fatigue, and showing real business impact. Training the Next Generation: Will AI kill the associate path? Max offers a candid take on why firms may not need as many junior lawyers—and why that doesn’t mean the end of meaningful legal careers. Product or People? Mary and Max dive into why early buyers are betting more on startup teams than the tech itself—and how Legora is trying to earn that trust. The End of Point Solutions: With AI tools multiplying daily, Max predicts a shakeout is coming—and explains why orchestration and seamless user experience will win. Whether you're trying to roll out legal AI across a global firm or just keeping tabs on the tools reshaping the industry, this episode delivers a rare, candid look from a founder at the center of the storm. Follow Mary on LinkedIn Rate and review on Apple Podcasts

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

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.  

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 challenges legal professionals face as they navigate their careers. In this episode, Kathy unpacks the key skills that separate high-potential leaders from those who plateau. Whether you’re looking to develop a powerful leadership presence, master the art of influence, or learn how to tell your career story in a way that makes your value impossible to ignore, Kathy shares actionable insights that every legal professional can use to take their career to the next level. In this episode: Developmental vs. Behavioral Coaching: Understanding the difference and why developmental coaching is critical for high achievers. How to Stand Out: Why simply doing your job well isn’t enough—and what it really takes to get noticed and promoted. The Power of Learning Agility: How embracing discomfort and taking on new challenges is the ultimate predictor of long-term success. Mastering Influence and Persuasion: The three essential skills that can make or break your career trajectory. Why Storytelling Matters: How to communicate your value in a way that leaders actually pay attention to. Navigating Office Politics: Practical strategies for managing up, building relationships, and positioning yourself for leadership roles. The Value Formula: A simple framework to articulate the impact of your work and make it clear why you’re indispensable. Follow Mary on LinkedIn Rate and review on Apple Podcasts

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 providers gives him invaluable insights into the ecosystem's evolution. In this episode: ·        The Spectrum of Transformation: How organizations vary widely in their readiness and approach to change, from those racing toward 2030 to those still operating like it's 1998. ·        Drivers of Change: Understanding what's accelerating transformation in both corporate legal departments and law firms, and why some resist despite mounting pressure. ·        The Technology Paradox: Why technology alone isn't the answer, but serves as a powerful catalyst for broader organizational change. ·        Market Consolidation: Insights into the consolidation trends across legal tech, service providers, and law firms, and what it means for the industry. ·        The Big Four's Impact: Analysis of KPMG's entry into the U.S. legal market and its potential implications for traditional law firms. ·        Investment Opportunities: Why investors remain bullish on legal tech and services, despite the industry's unique challenges. ·        Change Management: Practical advice on balancing current operations (80%) with future transformation (20%) and creating effective enterprise-wide change. ·        2025 Predictions: Why this year could mark meaningful advancement in both tech adoption and process transformation across the legal ecosystem. For anyone interested in the future of legal services, technology adoption, or organizational transformation, this conversation offers valuable insights from one of the industry's most experienced voices. Goodwin at HumanX Follow Mary on LinkedIn Rate and review on Apple Podcasts

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: ·        The Unicorn Dilemma: Remember when legal ops professionals were expected to do it all? Mary and Frances explore why that "strategic generalist" role seems to be fading, and what that means for the profession. ·        Splitting at the Seams: As legal ops splinters into specialized roles like data analytics and vendor management, is this evolution or fragmentation? And does it matter? ·        Hiring Horror Stories: Frances gets real about what happens when companies hire for legal ops without really knowing what they need—and how to avoid this common pitfall. ·        The Consultant Question: Are companies bypassing internal legal ops teams for external expertise? Mary and Frances tackle this trend head-on. ·        Going Global: Why the lack of consistent standards for legal ops roles worldwide is becoming a real problem, and what we can do about it. ·        The Big Question: Can legal ops recapture its revolutionary spirit, or is it destined to become just another corporate function? If you've been feeling the shift in legal ops—or wondering if you're imagining it—this conversation will hit home. Join Mary and Frances for an honest look at where legal ops stands today, and what it'll take to shape its future. Goodwin at HumanX Follow Mary on LinkedIn Rate and review on Apple Podcasts

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