Pearls On, Gloves Off: The Legal Innovation Podcast
Join Mary O'Carroll as she sits down with General Counsel, Chief Legal Officers, and industry pioneers to tackle the debates reshaping legal services and technology. Presented by Workday.
Episodes
#101 - Ford's Warning Shot: Adapt or Get Left Behind
Mary sits down with Darth Vaughn, Associate General Counsel and Managing Director of Policy and Legal Ops at Ford Motor Company, for a candid conversation about what it actually looks like when one of the world's largest legal departments stops waiting and starts building. They dig into why the billable hour model is structurally broken, what Ford actually expects from its outside counsel, why AI
#100 - The Future of Legal Is Already Here - A Conversation with CLO Eric Greenberg
Mary sits down with Eric Greenberg, EVP, Chief Legal Officer, and Corporate Secretary at Cox Media Group, for a milestone 100th episode conversation about what it actually takes to lead a legal department through transformation. They dig into why AI governance is really an anthropology problem, why buying software is the beginning not the end, the future of big law and outside counsel relationship
#99 - Who Is Sandstone? Inside Legal Tech's Most Talked-About Company
Mary sits down with Nick Fleisher, Co-Founder and CEO of Sandstone, to pull back the curtain on legal tech's fastest-rising company. They dig into why great software still matters in the age of AI, how Sandstone is solving the permissions and context problem that's plagued in-house legal for years, why law firms will never out-build tech companies, and how an AI-native team is redefining what it m
#98 - Anna Richards
Mary sits down with Anna Richards, Head of Community at Brightflag, to catch up on what's actually happening on the ground in legal ops right now. They dig into the shifting skill sets legal ops leaders need, how to think about building a tech stack from scratch, and why the job keeps getting harder even as expectations keep climbing. This episode is presented by Workday. Join Mary's Substack Comm
#97 - The Senior Talent Problem Nobody Wants to Talk About
In today's episode, Mary sits down with James O'Dowd, CEO and founder of Patrick Morgan, to explore what legal can learn from the PE and AI disruption already reshaping accounting and consulting. James breaks down why governance is the real unlock private equity brings, how compensation models are shifting away from legacy profit-sharing, and why cultural buy-in ultimately determines whether any o
#96 - Curating AI Tools for a Global Law Firm
In today's episode, Mary sits down with Ilona Logvinova, Chief AI Officer at HSF Kramer, to talk about what it actually takes to turn a global law firm into an AI native organization. They cover why the Chief AI Officer title means something different from innovation, what it takes to build a forward deployed legal engineering function, and why the real edge isn't buying technology - it's the peop
#95 - Legal Will Lead The AI Revolution
In today's episode, Mary sits down with Aine Lyons, Senior Vice President & Deputy General Counsel and Chief Strategy Officer at Workday, to talk about what it actually takes to build a modern legal department. They cover why Aine deliberately designed Workday's function without a traditional legal ops silo, what it means to reskill every lawyer in the department, and why guardrails and governance
#94 - Who Needs Associates? Pierson Ferdinand's Partner Only Model
In today's episode, Mary sits down with Michael Pierson and Joel Ferdinand, Co-Chairmen of Pierson Ferdinand, and Christina Wojcik, their Chief Innovation Officer. Together, they break down what it actually takes to build the law firm of the future and why buying AI tools without rethinking your structure, culture, and compensation model is the wrong place to start. This episode is presented by Wo
#93 - Harvey CEO: Individual Productivity Is a Trap
In today's episode, Mary sits down with Winston Weinberg, CEO and Co-Founder of Harvey.ai, to talk about what it actually takes to transform legal - and why buying AI tools without rethinking how your entire organization operates is the wrong place to start. This episode is presented by Workday. ~~~ Thank you to our sponsors for making this show possible. Wordsmith.ai Brightflag ~~~ Support the
#92 - "AI is our Kodak Moment"
In today's episode, Mary sits down with Virginia Briggs, CEO and Managing Partner of MinterEllison, to talk about what real AI transformation actually looks like inside a law firm. This episode is presented by Workday. ~~~ Thank you to our sponsors for making this show possible. Wordsmith.ai Kodex Brightflag ~~~ Support the show! Join Mary's Substack Community Follow Mary on LinkedIn Rate and
#91 - Wordsmith CEO: 70% of Legal Tech Gone by 2027
When Ross McNairn realized his legal career meant reviewing 15,000 documents by hand, he didn't just question the system - he rewrote it. Literally. In this episode, Mary sits down with the Wordsmith ai founder to unpack what happens when a former lawyer turned engineer takes on legal's biggest inefficiencies and why AI is about to redraw the boundaries between in-house teams and law firms. From e
#90 - Clients "Do Their Own Research." That's A Problem for Law Firms
This episode of Pearls On, Gloves Off is powered by Workday. Learn more at workday.com. In this episode, Mary sits down with Claire Hart, Chief Operating Officer, Chief Legal Officer, and Board Member at Groq, to talk about what legal leaders should expect in the AI era - from their law firms, their teams, and themselves. With senior leadership roles at Google, Blizzard, and Genies, Claire brings
#89 - AT&T's New In House Law Firm
In this episode of Pearls On, Gloves Off, Mary sits down with Bill Ryan, Senior Vice President and Chief Compliance Officer at AT&T, and Ava Guo, Assistant Vice President and Senior Legal Counsel, to talk about leading through the AI inflection point inside a global legal department. As tools evolve monthly and expectations rise, the real differentiator isn't access to technology, it's execution.
#88 - Big Law: Record Profits… For Now
In this episode of Pearls On, Gloves Off, Mary sits down with Mike Abbott, Head of the Thomson Reuters Institute, to unpack the paradox: how can firms be thriving on paper while the ground shifts beneath them? Clients are tightening spend. Work is moving down-market and in-house. AI adoption is accelerating, especially on the client side, yet most of the industry still can't measure ROI beyond "ti
#87 - Updates & Hot Takes with Alex Su
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 convers
#86 - Mary Talks to her Digital Twin
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 (podcas
#85 - Edward Jones CLO Is Moneyball-ing Legal Risk
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 bri
#84 - Resetting the Relationship with Outside Counsel
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 t
#83 - Recruiting Gen Z Lawyers in a Broken System
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 str
#82 - Deloitte Prices for Outcomes. Law Firms Will Too.
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
#81 - The New Structure of AI Powered Law Firms
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
#80 - Harvey AI's GC: Lawyers Are 20x More Efficient... Now What?
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
#79 - In House Career Growth: Being a Great Lawyer Isn't Enough
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 tra
#78 - The Joyful Legal Team
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 shar
#77 - Do Law Firms Actually Want Innovation?
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 stubb
#76 - Why "Brilliance" Doesn't Sell: Rainmaker Strategies for 2025
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 selli
#75 - Owning the AI Narrative (Before Someone Else Does)
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-dri
#74 - From the Ground Up: Building Legal Ops with Sean Houston
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 sha
#73 - Futurist Says: Legal's Real Risk Is Playing It Safe
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 o
#72 - Moderna GC's AI Strategy
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 l
#71 - How to Hire (and Get Hired) in Legal Ops
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
#70 - Data, AI, and the New Legal Ops Playbook
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 bre
#69 - Why VCs Are Betting Billions On Legal Tech
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
#68 - Law Firms Enter The AI Arms Race
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-foun
#67 - The Multinational CLO
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
#66 - So you wanna be a GC?
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
#65 - What It Really Takes to Be a CLO Today
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
#64 - Why Playing by the Rules Won't Get You Promoted
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 ro
#63 - Is 2025 The Year Law Firms Finally Transform? - A Conversation with Matt Sunderman, CEO of Harbor Global
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
#62 - Is Legal Ops Losing Momentum?
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 i
#61 - If It's Scary, It's Good: How TravelPerk's GC is Reimagining Legal Services
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 ser
#60 - No-Redline Revolution: Redefining In-House Legal with Rippling GC Vanessa Wu
In this episode, Mary sits down with Vanessa Wu, the General Counsel at Rippling—a fast-growing platform unifying HR, IT, finance, and more for businesses around the globe. From eliminating contract negotiations by design to harnessing AI for everyday legal work, Vanessa shares how she's freeing up her team for the most important, high-level tasks. She also opens up about navigating a crisis when
#59 - Lawyers vs. the Commute: Making the Office Worth It, with Emily Botello from CBRE
"Flexibility is here to stay." – Emily Botello In this episode, Mary chats with Emily Botello from CBRE about how the legal industry is reinventing its office spaces. From single-size offices and neighborhoods of shared desks to seamless technology and thoughtful change management, Emily shares what's working, what's not, and how legal teams are adapting to a world where no two days look the same.
#58 - Open to Weirdness: Brian Israel on Leading Legal at Anthropic
"Sometimes the right answer for Anthropic would be things that 99% of tech companies wouldn't even consider. You have to be appropriately open to weirdness—not weirdness for the sake of weirdness, but tied to what we're trying to achieve in the world." —Brian Isreal, GC, Anthropic In this episode, Mary sits down with Brian Israel, General Counsel at Anthropic, to explore what it's like to oper
#57 - From Navy Pilot to General Counsel: IPOs and Legal Innovation with Phil Mazzara
This special episode was recorded live at Goodwin's Tech Retreat in San Francisco, where Mary sits down with Phil Mazzara, General Counsel of Astera Labs, to explore the evolving role of the general counsel in today's rapidly changing technological landscape. Phil's journey is nothing short of extraordinary. Before becoming an attorney, he spent over a decade on active duty as a Navy pilot, bringi
#56 - Ending the Billable Hour: Chris Grant's Mission to Transform Legal Services
Welcome to another episode of Pearls On, Gloves Off with your host, Mary O'Carroll, Chief Operating Officer at Goodwin. Today, Mary dives deep with Chris Grant, Head of Legal Market Engagement at HSBC, to unravel the evolving landscape of the legal industry. Chris Grant isn't your typical legal professional. Frustrated by the glacial pace of change in an industry resistant to innovation, Chris has
#55 - Redefining Law Firms: Navigating Change with Legal Visionary Reena SenGupta
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 Reena SenGupta, a longtime analyst, writer, consultant, and thought leader in the global legal industry with almost 30 years of experience. Reena's journey is impressive. She is an entrepreneur and journalist who has developed some of the most
#54 - Navigating Successful Exits: Joe Hyrkin on Leading Issuu to a Nine-Figure Sale
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 Joe Hyrkin, Chief Executive Officer of Issuu, a leading digital publishing platform that's transformed how content is shared and consumed online. With over 30 years of experience in startup and growth technology leadership across Silicon Val
#53 - Building the Law Firm of the Future: A Conversation with Goodwin's Leaders
Welcome to another episode of Pearls On, Gloves Off with your host, Mary O'Carroll, Chief Operating Officer at Goodwin. Today, Mary sits down with Goodwin's leaders—Anthony McCusker, Chair, and Mark Bettencourt, Managing Partner—for an insightful conversation about the firm's unique culture, its client-centric approach, and the future of the legal industry. Anthony McCusker is widely recognized
#52 - From Improv to AI: HubSpot CLO Alyssa Harvey Dawson
Welcome to another episode of Pearls On, Gloves Off with your host, Mary O'Carroll, Chief Operating Officer at Goodwin. After a brief hiatus, we're back, and this episode features a fascinating conversation with Alyssa Harvey Dawson, Chief Legal Officer at HubSpot. With over 20 years of experience leading legal teams at major companies like Gusto, Sidewalk Labs, Netflix, and Autodesk, Alyssa share
#51 - Mary's Next Big Move and Life Lessons with Leslie Henthorn from Ironclad
Welcome to another episode of "Pearls On, Gloves Off," where we dive deep into the challenges and innovative strategies within the legal and corporate world. In this episode, we flip the tables. Mary O'Carroll, the powerhouse host you've come to know, becomes the guest as Ironclad's Chief Marketing Officer, Leslie Henthorne, steps in to host. This episode is filled with heartfelt reflections,
#50 - Career Transitions and The Keys to Team Building with Mick Cox from Procore Technologies
Welcome to another episode of "Pearls On, Gloves Off," where we dive deep into the challenges and innovative strategies within the legal and corporate world. Today, Mary is joined by Mick Cox, the VP of Legal Operations at Procore Technologies. They dive deep into the evolution of legal operations and the dynamic journey of growing a legal team from scratch. They explore the challenges and triumph
#49 - Innovating Legal Ops with Andrew Krug from Twitch
Welcome to another episode of "Pearls On, Gloves Off," where we dive deep into the challenges and innovative strategies within the legal and corporate world. Today, our guest is Andrew Krug, Head of Legal Operations at Twitch, the video live streaming service known for its focus on video game live streaming and esports competitions. Andrew brings a wealth of experience from diverse industries incl
#48 - CLOC Presidents Roundtable, with Jenn McCarron and Mike Haven
Welcome to another episode of "Pearls On, Gloves Off," where we dive deep into the challenges and innovative strategies within the legal and corporate world. Today, we bring together all three past and current CLOC presidents: Jenn McCarron, Mike Haven, and Mary O'Carroll. They discuss everything from Legal Ops, to AI, blockchain, and the meaning of life. In this Episode • The history of legal ops
#47 - Thinking Upstream: Strategic Legal Leadership with GC Matt Campobasso
Welcome to another episode of "Pearls On, Gloves Off," where we dive deep into the challenges and innovative strategies within the legal and corporate world. Today, our guest is Matt Campobasso, the General Counsel and Corporate Secretary at Enfusion, a fintech company revolutionizing investment management through its cutting-edge software solutions. About the Guest Matt oversees the legal functio
#46 - Communicate Better at Work with Misha Glouberman, Author, Coach & Advisor
In this episode of Pearls On, Gloves Off, Mary is joined by Misha Glouberman, an acclaimed author, advisor, and coach who excels in the art of effective communication and managing difficult conversations. Together, they explore the intricate dance between analytic thinking and emotional understanding in the workplace. Mary and Misha delve into: • Effective Communication: Misha underscores the crit
#45 - Mary's Thoughts on CLOC Global Institute '24
Special Bonus Episode! Mary goes solo to share her thoughts following CLOC Global Institute (CGI) 2024, answering your burning questions in a special AMA format. Questions: What felt different to you about this year's CGI? What are your thoughts on where we are with AI? How can there be so many CLMs? Can you recap what you said in your speaking sessions? What comes next? Mary dives into the un
#44 - Change and Innovation in the Age of AI with Ashley John, Head of Legal Ops at Anglo American
Note from producer: This is an updated version that addresses an audio issue in the original. Thanks for bearing with us. In this episode of Pearls On, Gloves Off... Mary and Ashley John dig into the dynamic world of legal operations. Ashley, the Head of Legal Operations at Anglo American, brings a unique perspective from his background in mining and geology to his strategic role in a global mini
#43 - Creating Buy-In and Driving Efficiency with Anna Richards
In this episode of Pearls On, Gloves Off, Mary O'Carroll sits down with Anna Richards, Director of Global Legal Operations at John Deere. With over 15 years of experience, Anna brings deep insights from companies like Autodesk, Zendesk, and Micron Technology.Mary and Anna dig into: Transitioning to John Deere: Anna details her onboarding journey, where Deere laid the groundwork by first und
#42 - Strategic Solutions: Navigating Legal Operations Challenges with Dawn Hinz
In this episode of "Pearls On, Gloves Off," Mary sits down with Dawn Hinz, legal operations leader at Avery Dennison. Together, they dive into the nuances of leading and transforming the legal ops landscape. In The Episode: Exploring Strategy and Improvement: Dawn's role at Avery Dennison: strategy development, process enhancement, and resource optimization. She shares her methodologies in change
#41 - Breaking Glass and Taking Risks: Charlene Barone on Leadership in Legal Operations
In this episode of Pearls On, Gloves Off, Mary O'Carroll welcomes the formidable Charlene Barone, currently steering the ship as the Director of Legal Operations at the New York Times. Charlene, with her rich history traversing from contracts manager to legal ops leader, brings a wealth of knowledge from both the startup world and the franchise legal landscape of Orange Theory Fitness. A Tale of
#40 - The Magic of Curiosity, with Chris Clearfield
In this episode of Pearls On, Gloves Off, Mary O'Carroll sits down with Chris Clearfield, a true trailblazer in the world of leadership and management. As the CEO of Clearfield Group and the co-author of "Meltdown," Chris brings a fresh take on how to lead through the chaos and complexity of today's business landscape. Change Leadership, Not Management: Mary and Chris dig into why "change m
#39 - Mary's Guide to CLM
In this solo episode, Mary O'Carroll shares her insights on Contract Lifecycle Management (CLM). She explores: The Challenges of Contracts: Overview of common issues in contract processes and the potential for improvement. Ownership of CLM: Advocates for General Counsel to lead CLM processes, highlighting the strategic value of contracts data. Evolution of CLM Technology: From basic database syst
#38 - Legal Ops at Expedia: A Conversation with Mike Russell, Head of Global Legal Operations at Expedia Group
In this compelling episode of "Pearls On, Gloves Off," Mary hosts Mike Russell, a seasoned expert in legal operations and legal technology with a career spanning over three decades. From the dawn of internet technology in law firms to the current emphasis on efficiency and innovation, Mike shares invaluable insights into the evolution of legal ops and tech. The Journey Through Legal Tech Evoluti
#37 - From Military Police to Global Ops: Lessons in Leadership from Darek Kochman, Global Legal & Compliance Operations Leader at Kimberly-Clark
In this episode of Pearls On, Gloves Off Episode: Leadership and Learning with Darek Kochman Mary O'Carroll talks with Darek Kochman, Director of Global Legal Operations at Kimberly-Clark Corp, about his journey from the military to leading global operations. Here's what they cover: Diverse Background: Darek's path through the military, KPMG, and into legal operations showcases a non-traditional
#36 - Embracing AI in Law: A Conversation with Andrew Perlman on the Future of the Legal Profession
In this episode of Pearls On, Gloves Off: Join Mary O'Carroll in a riveting conversation with Andrew Perlman, a visionary in law and technology. As the Dean and Professor of Law at Suffolk University Law School, Perlman is pioneering the future of legal innovation. AI's Legal Landscape: Perlman takes us through the evolution of AI in law, forecasting its transformative impact while addressing c
#35 - Victim Mindset, Impostor Syndrome, and Subconscious Beliefs - Kim Kokoska, Mary's Executive Coach
In this episode of Pearls On, Gloves Off Mary sits down with her own own executive coach, Kim Kokoska, for a deep dive into the psychology of self-perception and empowerment. Listen in as they unpack some transformative ideas: Victim vs. Observer Mindsets: dissecting the 'victim triangle', featuring the roles of victim, persecutor, and rescuer. They explore how we often oscillate between these r
#34 - Flex Talent For The Win! With Trista Engel & Jessica Markowitz, executive leaders at Paragon Legal
Mary O'Carroll welcomes the dynamic duo of Trista Engel and Jessica Markowitz, leaders at Paragon Legal and co-founders of Calyx Capital Partners. Both seasoned MBAs from the University of Chicago Booth Business School, they share insights on reinventing legal talent in today's fast-paced world. Flex Talent Revolution: Mary and her guests unpack the concept of flex talent. They argue it's not ju
#33 - Legal Ops Is Not a Service Org! With Shiela Dusseau, Head of Legal Ops, Ferring Pharma
In this episode of "Pearls On, Gloves Off," host Mary O'Carroll sits down with Sheila Dusseau, whose transition from finance to legal operations has been nothing short of a masterclass in adaptability and strategic thinking. Busting Myths: Shiela and Mary debunk common misconceptions about legal ops. Sheila advocates for a shift in perspective, from seeing legal ops as mere 'support' to recogniz
#32 - Ironclad CEO Jason Boehmig on Legal Ops & CLM
In this episode, I'm thrilled to sit down for an in depth conversation with the amazing Jason Boehmig, CEO of Ironclad. Here's what we cover: Jason's Unique Path: Discover how Jason transitioned from investment banking to law, setting the stage for his future endeavors. The Birth of Ironclad: Jason delves into the origins of Ironclad, highlighting the pivotal moments and decisions. Community at t
#31 - Offshore Your Legal Ops and More Advice From Abigail Nornoo, Head of Legal Ops at Standard Chartered Bank
In this episode, Mary interviews Abigail Nornoo, Global Head of Operations for Legal, CoSec & Investigative Services at Standard Chartered Bank. She spearheads a team of over 30 professionals, reshaping the landscape of legal ops. From Ghana to London: Abigail recounts her remarkable journey, detailing her transition from Ghana to the heart of London's banking scene, and the inception of her ex
#30 - How Salesforce Does Legal Ops with Léo Murgel, SVP Legal at Salesforce
In this episode of Pearls On, Gloves Off, go behind the curtain of legal ops at Salesforce with their SVP of Legal and Corporate Affairs Léo Murgel. Topics: From IT mergers to legal ops, Léo discusses the transition Unveiling the pillars of legal ops support and strategy AI's revolutionary role at Salesforce and the legal realm Legal ops duties—what they entail, their significance Léo's personal
#29 - Legal to COO, Centralizing vs. Decentralizing, and the Future of Legal Ops - Nitin Batra, Global COO for Citi Private Bank
In this episode of Pearls On, Gloves Off, we delve into the world of corporate operations with Nitin Batra, the Global Chief Operating Officer for Citi Private Bank. We explore his career journey, shedding valuable light on the influence of his legal operations background, the intricacies of corporate management, and the future of both the private banking sector and legal operations as a career p
#28 - Skipping the Firm, Finding a Mentor, Using GenAI - Stefan Nunn, Counsel at TravelPerk
Mary and Stefan Nunn unravel his journey from aspiring veterinarian to Legal Counsel at TravelPerk, highlighting the transformative power of legal operations, the innovative role of AI in the field, and the importance of entrepreneurial education and networking beyond the legal re From Vet Dreams to Legal Themes: A quirky leap from aspiring veterinarian to the legal counsel realm. Obstacles in th
#27 - Building Community, Reporting to CEOs, and Choosing Vendors with Sarah Irwin, Head of Legal at Tines
In this episode of Pearls On, Gloves Off: Community at its Finest. Dive into the Irish Tech General Council, chaired and founded by Sarah. The LinkedIn Guru. Sarah's insightful pieces on legal operations and tech are a must-read. A Seat at the Table. Why GCs need to report directly to the CEO in a rapidly expanding company. Choosing a CLM Provider. Sarah's playbook for picking a contract lifecycl
#26 - Hosting Ironclad Live with La'Resa Young, Sunil Jamal, Charles Hurr
In this special episode of Pearls On, Gloves off: This isn't your regular episode. It's a mashup of three scintillating conversations from the one and only contracts talk show, Ironclad Live, which Mary hosted in Dallas on September 7th. Dive in as Mary engages with legal luminaries from St. Jude Hospital, the Houston Texans, and L'Oréal. Conversation 1: St. Jude Hospital with La'Resa Young Mary
#25 - Empowering Legal Ops Leadership with Alex Kelly at Brightflag
On this episode, Alex Kelly, Co-Founder and COO at Brightflag, joins Mary in the world of podcasting, legal operations and the evolving landscape of legal technology. Alex shares his experience running a podcast called "In-House Outliers," featuring conversations with legal leaders, including general counsels and legal operations professionals. The guests on his podcast mainly come from Brightfla
#24 - Digital Transformation in Legal Ops with Aine Lyons at VMware
On this episode, Aine Lyons, Senior Vice President and Deputy General Counsel at VMware, joins Mary to talk about legal ops, her time at VMware and new technologies. More than a decade ago, Aine was approached by a former GC at VMware about taking on legal ops. She declined because she didn't know anyone in legal ops and didn't know anything about it. Times have certainly changed. Aine now sees
#23 - Engagement as a GC Superpower with Lisa Gilley at Higher Logic
On this episode, Lisa Gilley, Chief Legal Officer at Higher Logic, joins Mary to talk about, among other things, community and engagement and how the Higher Logic platform allows organizations to give their community a home where they can interact, share ideas, answer questions and stay connected. Engagement with customers is critical for customer retention in any community, and the legal communi
#22 - Creating Technology for Legal Ops with Katherine Roseveare and Alex Herrity at Adidas
On this episode, Katherine Roseveare, General Counsel - Global Functions, Global Operations and Legal Solutions, and Alex Herrity, Director - Global Legal Solutions at Adidas, join Mary to talk about managing technology in a global setting, the creative mindset of their legal team and building out a legal tech department and team from scratch. They talk through their creation of new legal technol
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