#76 - Why “Brilliance” Doesn’t Sell: Rainmaker Strategies for 2025
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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...
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#75 - Owning the AI Narrative (Before Someone Else Does)
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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...
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#74 - From the Ground Up: Building Legal Ops with Sean Houston
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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...
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#73 - Futurist Says: Legal’s Real Risk Is Playing It Safe
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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)...
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#72 - Moderna GC’s AI Strategy
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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...
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#71 - How to Hire (and Get Hired) in Legal Ops
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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...
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#70 - Data, AI, and the New Legal Ops Playbook
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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...
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#69 - Why VCs Are Betting Billions On Legal Tech
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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,...
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#68 - Law Firms Enter The AI Arms Race
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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...
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#67 - The Multinational CLO
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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...
info_outlineIn 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.