#87 - Updates & Hot Takes with Alex Su
Pearls On, Gloves Off
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...
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#86 - Mary Talks to her Digital Twin
Pearls On, Gloves Off
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: ...
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#85 - Edward Jones CLO Is Moneyball-ing Legal Risk
Pearls On, Gloves Off
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...
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#84 - Resetting the Relationship with Outside Counsel
Pearls On, Gloves Off
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...
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#83 - Recruiting Gen Z Lawyers in a Broken System
Pearls On, Gloves Off
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...
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#82 - Deloitte Prices for Outcomes. Law Firms Will Too.
Pearls On, Gloves Off
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...
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#81 - The New Structure of AI Powered Law Firms
Pearls On, Gloves Off
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:...
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#80 - Harvey AI’s GC: Lawyers Are 20x More Efficient... Now What?
Pearls On, Gloves Off
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...
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#79 - In House Career Growth: Being a Great Lawyer Isn’t Enough
Pearls On, Gloves Off
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...
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#78 - The Joyful Legal Team
Pearls On, Gloves Off
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...
info_outlineMary 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.
In this episode
- 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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