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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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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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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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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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.

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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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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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

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When Mary posted a question about the state of legal ops on LinkedIn, she didn't expect to spark such intense debate. But the responses revealed what many have been quietly wondering: has legal operations reached a turning point?

In this episode, Mary sits down with Frances Pomposo, Senior Director of Legal Technology Solutions at Cisco, to dig into this thorny question. With her deep experience in tech companies and time on CLOC's board, Frances brings a unique perspective on where legal ops has been—and where it might be heading.

In this episode:

·        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

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In this episode, Mary O'Carroll sits down with Andy Cooke, General Counsel at TravelPerk, a hyper-growth global tech unicorn providing business travel solutions. Andy, who previously built award-winning teams at Fnatic and Flash Entertainment, shares his innovative approach to legal operations and AI implementation. The conversation explores how legal departments can evolve beyond traditional service models to become true value creators in the age of AI.

Topics:

• Early adoption of AI in legal operations and the evolution from "dumb chatbots" to sophisticated AI solutions
• The changing 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 

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