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.

Follow Mary on LinkedIn

Rate and review on Apple Podcasts

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