Mary O'Carroll kicks off a new era of Pearls On, Gloves Off - independent, sponsor-curious, and still laser-focused on what's actually changing in legal. Her first guest in this new chapter is the person many listeners will recognize instantly: Alex Su. Former litigator, ex-legal tech sales leader, early "legal influencer," and now Chief Revenue Officer at Latitude.

This episode is a blunt conversation about the gap between buying innovation and actually using it. Mary and Alex dig into why legal excellence by itself doesn't deliver business value, why so much AI adoption is still "innovation theater," and why integration (not hype) is the make or break factor for legal tech, legal services, and legal careers.

• The core thesis: Legal excellence alone doesn't cut it. If a lawyer, ALSP, or AI tool isn't embedded in the workflows, it won't stick.
• AI reality check: 2025 was the year of "buying"; 2026 will be about renewals, retention, and ROI.
• CLM is back: "Agents will replace workflows" didn't land (yet). Real SaaS infrastructure still matters, and AI works best layered into it.
• Disaggregation/right-sourcing is accelerating: Big Law moves upmarket, expanding room for ALSPs, flexible talent, and tech-enabled delivery.
• The Innovator's Dilemma for firms: Dropping "lower-value" work can erode stickiness, and invite new providers to move up the chain.
• Training is the looming issue: As work shifts and automates, the profession has to rethink where reps and apprenticeship come from.

For those thinking seriously about legal transformation, technology, and where the industry is headed, this conversation lays out what actually matters next.

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Mary O'Carroll isn't experimenting for fun, she's trying to solve one of legal's biggest scaling problems: the fact that the profession's best judgment and hard-earned experience still lives in people's heads, buried in laptops, or scattered across years of emails. So in this episode of Pearls On Gloves Off, Mary runs a real test: she trains a digital twin on essentially all of her content (podcasts, talks, blogs, speeches), and then sits down for a conversation with "Digital Mary" to find out whether a digital mentor can actually deliver useful guidance.

In this episode:

• Digital Mentors, Tested: Why Mary built a digital twin trained on decades of her content - and whether AI can realistically scale mentorship and judgment in legal.
• Legal Ops, Rewritten: How the function has evolved from managing outside counsel spend to driving technology, data, and GenAI-enabled transformation.
• The Lawyer Skillset Is Shifting: Why trust, judgment, and relationship-building matter more than ever, even as training models struggle to keep up.
• Tech Hype vs. Real Impact: How to think "problem first, tool second," and why foundational legal tech still delivers massive value alongside AI.
• Pressure on the Billable Hour: What AI exposes about law firm economics, pricing, and the growing need for right sourcing and true partnership.

If you're thinking about training, legal ops scale, AI disruption, or the future of law firm economics, this episode is a rare, real-time look at how the profession might start "bottling" expertise, and what it will take to do it well.

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Keir Gumbs, Chief Legal Officer at Edward Jones, isn't here to maintain the status quo. He joined the largest U.S. financial services firm not to run legal as usual - but to lead a transformation. In this episode, Keir and Mary talk candidly about what it takes to build a modern legal function inside a legacy institution - and why the traditional law firm model may not survive the decade.

Keir brings a rare 360° view of the legal world, with leadership roles at Uber, Broadridge, Covington, and the SEC. Now, he's putting that experience to work reshaping how legal, compliance, and risk teams partner with the business and what true enablement looks like.

In this episode:

• Transformation Playbook: Why Keir spent his first year meeting with 500+ team members - and what it taught him about culture and leadership.
• Shared Services, Shared Wins: How he's connecting legal, compliance, and risk through a shared services model that's breaking down silos and boosting speed.
• Enable First, Protect Second: Keir's core legal philosophy - and how it's changing how his team shows up across the organization.
• Law Firm Economics, Under Fire: Keir sounds the alarm on unsustainable rate hikes and why smaller, specialized firms are increasingly winning the work.
• Outcome Over Hours: What he's looking for in alternative fee models, and the reality check law firms need to hear.

If you're thinking about legal transformation, technology, or the future of firm partnerships, this conversation is a blueprint for what's next.

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Mary O'Carroll welcomes Stephanie Hamon (Global Head of Legal External Engagement, HSBC) to explore how in‑house legal teams are rethinking their relationships with law firms, vendors, and the broader legal ecosystem. With experience spanning Barclays, Norton Rose Fulbright, and now HSBC, Stephanie brings a uniquely global and pragmatic perspective to legal transformation - from process redesign to AI's impact on delivery models.

In this episode:

• The new panel model: Stephanie explains how HSBC is moving beyond transactional vendor management toward deeper, collaborative partnerships with firms and providers.
• Legal ops as a mindset: It's not just a function. Stephanie shares why ops is about how you think, not just who you hire.
• People, process, then tech: Before chasing the next tool, Stephanie urges legal teams to address foundational issues in process and data.
• Why consulting helps (at first): For legal departments overwhelmed by where to start, Stephanie outlines how consultants can build clarity and roadmaps before you hire in‑house.
• The death of the billable hour?: As AI and internal tooling reshape what gets sent outside, pricing models need to shift from time to value.
• Joint talent development: Stephanie makes a strong case for collaborative training between firms, clients, and academia to fix the broken legal talent pipeline.
• Three reasons we go external: Capacity, capability, and strategic insurance - and why each is evolving.
• Law firms under pressure: How client-side innovation is forcing firms to rethink delivery, pricing, and partnership structures.

If you've been trying to future‑proof your outside counsel strategy - or are wondering how AI is reshaping legal budgets, this conversation is a clear-eyed, practical guide to what's next.

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Legal recruiters and podcast hosts Genevieve Riccardelli and Jennifer Soltau join Mary to unpack how law-firm hiring is being turned on its head. They run entry-level recruiting at Goodwin and see the shift happening in real time. Their perspective on what students want, what firms are doing, and where this all goes next is honest, practical and very needed.

In this episode:

• OCI is losing its structure. What used to be a predictable, school-run process has fractured. Firms are now interviewing students before grades, before exams and sometimes before classes even begin.
• Recruiting years into the future. Firms are locking in talent 2 or 3 years ahead without knowing what their practices or clients will actually need. That mismatch shows up later in churn, confusion and a lot of second guessing.
• The in-house pull. More students want in-house careers and some companies are now hiring straight out of law school. The long-standing assumption that firms are the only training ground is shifting.
• A new type of candidate. Students with previous careers in biotech, business or tech are clearer about their goals and often move through the process faster. Their presence is reshaping expectations on both sides.
• What firms need to rethink. Copying whatever another firm does will not cut it anymore. The future belongs to firms that listen, experiment and build programs that match what talent actually wants.

If you want to understand how law-firm recruiting broke and what the next generation of lawyers is really looking for, this conversation is worth your time.

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Mary O'Carroll welcomes Ben Campbell (General Counsel, Deloitte) to unpack how law firms can—and must—learn from consulting and advisory firms. With a career that spans the DOJ, BigLaw, and now a top in‑house role, Ben offers a unique vantage on how governance, compensation, pricing and talent models are evolving.

In this episode:

• Outcome‑based billing: Ben walks through how outcome‑based (versus hourly) billing shifts incentives, aligns with the client, and drives efficiency.
• Governance at scale: At Deloitte, the partnership model combines with a layered board/CEO structure—getting buy‑in from hundreds of partners and deploying resources across businesses.
• Talent & career flexibility: Moving beyond "lockstep" life‑path models, Ben discusses how allowing flexible progression and acknowledging different career goals helps retain and grow talent.
• AI & disruption: The "pyramid" leverage model (many junior + a few senior) is under pressure. Routine tasks will be automated; strategic judgment will remain the premium play.
• What law firms can borrow now: From shared back‑offices and staffing flexibility to outcome‑pricing and more dynamic governance—Ben makes the case for law firms to evolve before "behind" becomes the new norm.

If you're wondering how the next chapter of legal and professional services might look, this conversation is a must‑listen—smart, candid and forward‑leaning.

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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.

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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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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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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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