Pearls On, Gloves Off
Smooth operations keep businesses afloat – but what makes them successful? “Pearls On, Gloves Off” is a new podcast where Legal Ops legend Mary O’Carroll and a motley crew of guests share their insider knowledge from running high-performing businesses. Join us for insightful conversations with some of today’s most respected leaders and luminaries.
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#81 - The New Structure of AI Powered Law Firms
11/11/2025
#81 - The New Structure of AI Powered Law Firms
When many law‑ and consulting‑firms ask “Which AI tool do we buy?” they’re missing the bigger shift: the very business model is changing. In this episode, Mary sits down with David Duncan and Tyler Anderson—two long‑time service‑firm innovators—to explore how AI is not just a new tool, but a structural force reshaping professional services: staffing models, pricing, talent, and even the nature of expertise. In this episode: The pyramid unravels: We revisit the traditional "analyst → manager → partner" model and why AI is eroding the base layers. From pyramid to obelisk: David and Tyler explain why the future staffing architecture looks more like a narrow obelisk than a wide pyramid. AI‑native vs. retrofit: Are you building your firm around AI or simply bolting AI on? The difference is profound. Pricing and incentives under pressure: If AI reduces hours and increases speed, how do firms preserve value and avoid racing toward the billable‑hour death spiral? Talent, apprenticeship & judgement: With junior work being automated, how will younger professionals develop deep judgment? What happens to the craft of the profession? Incumbents vs. attackers: Why nimble AI‑first boutiques may have the attacker’s advantage, and what legacy firms must do to remain relevant. Opportunity vs. risk mindset: David closes with a powerful framing—see AI not as a threat to be managed but as an opportunity to be seized. If you’re in legal or professional services and wrestling with how AI fits into your firm’s model—not just your tech stack—this is a must‑listen. Explore Goodwin’s Strategies for Winning Deals series to gain a competitive edge in closing your next deal:
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#80 - Harvey AI’s GC: Lawyers Are 20x More Efficient... Now What?
10/28/2025
#80 - Harvey AI’s GC: Lawyers Are 20x More Efficient... Now What?
In this episode of Pearls On, Gloves Off, Mary O’Carroll sits down with John LaBarre, General Counsel of Harvey. From Google to Snowflake and now a leader in legal AI, John’s career reflects the tech world’s evolution. Together, they dig into the pivotal moment we’re living through — when generative AI enters the legal profession not as a futuristic idea but as a productivity‑enhancer in real time. In this episode: Why legal is ripe for AI: He explains how the legal profession acts as a “low‑hanging fruit” for generative AI, given its massive volumes of unstructured data and repetitive tasks. Re‑learning technology: Generative AI isn’t like a perfect calculator. John argues lawyers must shift from expecting “the correct answer” to co‑working with predictive tools: prompting them, reviewing them, validating them. Measuring ROI: From the in‑house perspective, it’s about doing more with the same budget. John shares examples where what used to be a 30–40 hour review became a 2–3 hour job thanks to AI. Law firms, adoption & the billable hour paradox: The conversation pivots to law firms — how they adopt AI, the challenges of traditional measurement (billable hours), and why this moment might represent another nail in that coffin. What’s next: They explore the next three‑to‑five‑year horizon — what would make AI truly transformative, what still needs to happen, and why “agents” handling NDAs or contract workflows aren’t far off. If you’re involved in legal operations, in‑house counsel, or law firm innovation, this episode offers actionable insight into how legal work is changing—and what you should be doing right now to keep up.
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#79 - In House Career Growth: Being a Great Lawyer Isn’t Enough
10/14/2025
#79 - In House Career Growth: Being a Great Lawyer Isn’t Enough
In this episode, Mary O’Carroll sits down with Rachel St. Peter, General Counsel at Nestlé Health Sciences US, to unpack a bold career move: stepping into legal ops mid-career to grow beyond the “good lawyer” baseline. From leading global transformation out of Switzerland to reshaping her executive presence and business fluency, Rachel explains how ops experience changed her leadership—and her trajectory. They also dig into the future of in-house legal: AI realities, law firm pricing shakeups, and what the next generation of GCs must bring to the table. In this episode: Why being a great lawyer isn’t enough—and what Rachel did about it How a legal ops role built her executive presence and changed her leadership style What she’s doing differently as GC—from tech tips in team meetings to smarter firm scoping The shift from client-service thinking to true cross-functional business partnership How law firm billing must evolve alongside AI adoption—and what real transparency looks like Advice for anyone considering a strategic detour: when to take the lateral move and why If you’re thinking about how to future-proof your legal career—or how to lead with more impact—this episode will challenge the way you think about roles, risk, and reinvention.
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#78 - The Joyful Legal Team
09/30/2025
#78 - The Joyful Legal Team
In this episode of Pearls On, Gloves Off, Mary sits down with Jacqueline Lee, Senior Vice President and General Counsel at Flynn Group, to unpack what it takes to lead legal, compliance, and risk functions at scale. Flynn is the parent company behind brands like Panera, Taco Bell, Wendy’s, Planet Fitness, and more, with 75,000+ employees across the U.S., Australia, and New Zealand. Jacqueline shares her journey from big law to being unexpectedly tapped for a GC role just a year into her in-house life. Along the way, she reveals what’s really changed (and what hasn’t) in that transition — especially around how legal advice must shift to be more strategic, practical, and business-aligned. In this conversation, you’ll learn: How to translate your legal skills for non-lawyer clients. Jacqueline stresses the importance of tailoring advice to how business leaders think and act — not how lawyers talk. Why “perfect information” is a myth in-house. You’ll hear how GCs must balance risk, ambiguity, and the need to move fast. How to lead through crisis and uncertainty. Jacqueline’s leadership during the pandemic reveals lessons in transparency, empathy, and restoring a feeling of control. How to demonstrate real value to the business. She explains her shift from narrative legal reports to visual dashboards, metrics tied to core business KPIs, and proactive reporting. The case for in-house litigation. Flynn handles much of its litigation internally; Jacqueline explains how they pick which matters to pursue internally vs. outsource — and why she still loves law. How to recruit, grow, and scale a legal team. We dig into her hiring philosophy, aligning on values, and the challenges of hybrid teams. Pricing and partnership with outside counsel. Jacqueline critiques the inefficiencies of hourly billing and shares how value-based arrangements can align incentives and build trust. If you’re an aspirational in-house counsel or a legal leader grappling with how to prove impact, this episode is packed with insights you can start applying now.
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#77 - Do Law Firms Actually Want Innovation?
09/16/2025
#77 - Do Law Firms Actually Want Innovation?
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.
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#76 - Why “Brilliance” Doesn’t Sell: Rainmaker Strategies for 2025
09/02/2025
#76 - Why “Brilliance” Doesn’t Sell: Rainmaker Strategies for 2025
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 .
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#75 - Owning the AI Narrative (Before Someone Else Does)
08/19/2025
#75 - Owning the AI Narrative (Before Someone Else Does)
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.
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#74 - From the Ground Up: Building Legal Ops with Sean Houston
08/05/2025
#74 - From the Ground Up: Building Legal Ops with Sean Houston
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.
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#73 - Futurist Says: Legal’s Real Risk Is Playing It Safe
07/22/2025
#73 - Futurist Says: Legal’s Real Risk Is Playing It Safe
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.
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#72 - Moderna GC’s AI Strategy
07/08/2025
#72 - Moderna GC’s AI Strategy
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.
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#71 - How to Hire (and Get Hired) in Legal Ops
06/24/2025
#71 - How to Hire (and Get Hired) in Legal Ops
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.
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#70 - Data, AI, and the New Legal Ops Playbook
06/10/2025
#70 - Data, AI, and the New Legal Ops Playbook
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.
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#69 - Why VCs Are Betting Billions On Legal Tech
05/27/2025
#69 - Why VCs Are Betting Billions On Legal Tech
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.
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#68 - Law Firms Enter The AI Arms Race
05/13/2025
#68 - Law Firms Enter The AI Arms Race
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.
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#67 - The Multinational CLO
04/29/2025
#67 - The Multinational CLO
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.
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#66 - So you wanna be a GC?
04/15/2025
#66 - So you wanna be a GC?
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.
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#65 - What It Really Takes to Be a CLO Today
04/06/2025
#65 - What It Really Takes to Be a CLO Today
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.
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#64 - Why Playing by the Rules Won’t Get You Promoted
03/19/2025
#64 - Why Playing by the Rules Won’t Get You Promoted
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.
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#63 - Is 2025 The Year Law Firms Finally Transform? - A Conversation with Matt Sunderman, CEO of Harbor Global
03/04/2025
#63 - Is 2025 The Year Law Firms Finally Transform? - A Conversation with Matt Sunderman, CEO of Harbor Global
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.
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#62 - Is Legal Ops Losing Momentum?
02/18/2025
#62 - Is Legal Ops Losing Momentum?
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.
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#61 - If It's Scary, It's Good: How TravelPerk's GC is Reimagining Legal Services
02/04/2025
#61 - If It's Scary, It's Good: How TravelPerk's GC is Reimagining Legal Services
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!
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#60 - No-Redline Revolution: Redefining In-House Legal with Rippling GC Vanessa Wu
01/21/2025
#60 - No-Redline Revolution: Redefining In-House Legal with Rippling GC Vanessa Wu
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!
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#59 - Lawyers vs. the Commute: Making the Office Worth It, with Emily Botello from CBRE
12/31/2024
#59 - Lawyers vs. the Commute: Making the Office Worth It, with Emily Botello from CBRE
“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!
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#58 - Open to Weirdness: Brian Israel on Leading Legal at Anthropic
12/16/2024
#58 - Open to Weirdness: Brian Israel on Leading Legal at Anthropic
“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:
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#57 - From Navy Pilot to General Counsel: IPOs and Legal Innovation with Phil Mazzara
12/03/2024
#57 - From Navy Pilot to General Counsel: IPOs and Legal Innovation with Phil Mazzara
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:
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#56 - Ending the Billable Hour: Chris Grant’s Mission to Transform Legal Services
11/19/2024
#56 - Ending the Billable Hour: Chris Grant’s Mission to Transform Legal Services
Welcome 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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#55 - Redefining Law Firms: Navigating Change with Legal Visionary Reena SenGupta
11/05/2024
#55 - Redefining Law Firms: Navigating Change with Legal Visionary Reena SenGupta
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 Reena SenGupta, a longtime analyst, writer, consultant, and thought leader in the global legal industry with almost 30 years of experience. Reena’s journey is impressive. She is an entrepreneur and journalist who has developed some of the most influential rankings and programs in the legal world. She was instrumental in creating the Chambers and Partners Guides in the mid-90s and the Financial Times Innovative Lawyers Program, which is about to celebrate its 20th anniversary. In 2001, Reena founded RSG Consulting, which quickly became a leading brand in the legal sector. Today, she heads up RSGI, a global think tank focused on building a sustainable future for the legal industry. Reena is also a seasoned public speaker and regular contributor to the Financial Times, always bringing fresh, forward-thinking perspectives to the table. In this episode: · The Changing Legal Landscape: Exploring how the legal industry has evolved over the past two decades, including shifts in mindset and practice. · Defining Innovation in Law: Discussing what innovation truly means in the legal context and how it’s being implemented in firms and legal departments. · The Impact of Generative AI: Examining how generative AI is transforming legal work, from automating routine tasks to enabling lawyers to focus on strategic, high-value activities. · The Future Role of Lawyers: Insights into what the lawyer of tomorrow looks like, including the skills and roles that will be essential in a changing industry. · Client Expectations and Pressures: Understanding what’s driving client expectations and how law firms can better meet their clients’ evolving needs. · Challenges and Opportunities: Addressing the obstacles holding back the industry and the exciting opportunities for growth and transformation. · Reena’s Predictions: Reena shares her predictions for the next 12 months and beyond, including the potential for law firms to become masters of their own data. If you enjoyed our conversation with Reena SenGupta, 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!
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#54 - Navigating Successful Exits: Joe Hyrkin on Leading Issuu to a Nine-Figure Sale
10/22/2024
#54 - Navigating Successful Exits: Joe Hyrkin on Leading Issuu to a Nine-Figure Sale
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 Joe Hyrkin, Chief Executive Officer of Issuu, a leading digital publishing platform that’s transformed how content is shared and consumed online. With over 30 years of experience in startup and growth technology leadership across Silicon Valley, New York, Asia, and Europe, Joe brings a wealth of knowledge from early-stage ventures to IPOs and successful exits. Under his 11-year leadership at Issuu, the company expanded its product offerings, increased revenue and profitability, forged partnerships with industry giants like Canva, Adobe, and HubSpot, and achieved a nine-figure exit in a challenging M&A landscape. In this episode: Navigating a Successful Exit: How Joe led Issuu to a nine-figure sale during a slow year for M&A and capital markets. Flexibility and Resilience: The importance of adaptability in leadership amidst unpredictable market conditions. Strategic Positioning: Tips on positioning your company to maximize future options, including building relationships with potential acquirers and advisors. The Evolving Role of Legal Counsel: Discussing how lawyers are now integral business advisors, not just legal advisors. Working Directly with CEOs: Joe’s advice to lawyers on effectively collaborating with CEOs versus in-house counsel. Building the Right Team: The value of surrounding yourself with advisors and talent who deeply understand your business and industry. Human Connections in Business: The significance of authentic relationships and trust in driving business success. If you enjoyed our conversation with Joe Hyrkin, 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!
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#53 - Building the Law Firm of the Future: A Conversation with Goodwin’s Leaders
10/08/2024
#53 - Building the Law Firm of the Future: A Conversation with Goodwin’s Leaders
Welcome to another episode of Pearls On, Gloves Off with your host, Mary O’Carroll, Chief Operating Officer at Goodwin. Today, Mary sits down with Goodwin’s leaders—Anthony McCusker, Chair, and Mark Bettencourt, Managing Partner—for an insightful conversation about the firm’s unique culture, its client-centric approach, and the future of the legal industry. Anthony McCusker is widely recognized as a preeminent adviser in corporate securities and partnership laws, with a primary focus on advising technology companies and their investors. He chairs the firm’s Executive Committee and is a member of its Management Committee and Allocations Committee. Mark Bettencourt has extensive experience in mergers and acquisitions, public offerings, private placements of debt and equity securities, securities law compliance, and technology transfer and licensing. He chairs the firm’s Management and Allocations Committees and serves on the Executive Committee. In this episode: Embracing a Unique Culture: Mary’s early observations about Goodwin’s collaborative, team-first attitude and what sets the firm apart. Forward Thinking Innovation: How Goodwin is driving change in the industry through novel solutions, technology, and AI that enhance client service. Client-Centric Approach: The importance of being deeply immersed in clients’ industries and providing holistic business advice beyond traditional legal services. The Changing Role of Legal Professionals: How the role of general counsel is evolving and what that means for law firms and lawyers. Building for the Future Generation: The significance of mentorship, apprenticeship, and providing lawyers with the tools and opportunities to thrive. The Power of Collaboration: The results of working together across all levels of the firm to achieve common goals and drive success. We hope you enjoy this engaging conversation that offers a glimpse into the future of law firms and how Goodwin is embracing change to better serve clients and support its people.
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#52 - From Improv to AI: HubSpot CLO Alyssa Harvey Dawson
09/24/2024
#52 - From Improv to AI: HubSpot CLO Alyssa Harvey Dawson
Welcome to another episode of Pearls On, Gloves Off with your host, Mary O’Carroll, Chief Operating Officer at Goodwin. After a brief hiatus, we’re back, and this episode features a fascinating conversation with Alyssa Harvey Dawson, Chief Legal Officer at HubSpot. With over 20 years of experience leading legal teams at major companies like Gusto, Sidewalk Labs, Netflix, and Autodesk, Alyssa shares her insights on navigating AI challenges, the evolving role of legal leadership, and what it takes to build strong legal operations in today’s complex, tech-driven landscape. In this episode: · The evolving role of general counsel as a strategic partner in business growth. · The importance of trust and data governance in legal teams’ approach to AI. · The challenges of balancing global regulations, customer expectations, and innovation. · Building a legal team that fosters business alignment and addresses customer needs. · Insights into HubSpot’s legal operations and their approach to managing AI, compliance, and data security. · Alyssa’s thoughts on the skills needed to succeed in today’s legal operations roles, including business judgment and adaptability. · The unexpected benefits of improv in developing leadership skills in a corporate setting. Enjoyed this conversation? Don’t forget to subscribe to Pearls On, Gloves Off for more insightful discussions with leading figures in the legal and corporate sectors. Share your thoughts and join the conversation on our social media channels.
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