Pearls On, Gloves Off: The Legal Innovation Podcast

Mary O'Carroll
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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.

  1. 21. Juli

    #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 means to build lean. This episode is presented by Workday. Join Mary's Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts

  2. 7. Juli

    #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 Community Follow Mary on LinkedIn Rate and review on Apple Podcasts ~~~ Thank you to our sponsors for making this show possible. Kodex

  3. 23. Juni

    #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 of it sticks. On AI, James unpacks the concept of "talent debt" and closes with a bold prediction: a major technology player acquiring a large professional services firm may not be as far off as it sounds. This episode is presented by Workday. ~~~ Thank you to our sponsors for making this show possible. Kodex

  4. 9. Juni

    #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 people and incentives behind it. This episode is presented by Workday ~~~ Thank you to our sponsors for making this show possible. Wordsmith.ai Kodex ~~~ Join Mary's Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts

  5. 26. Mai

    #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 matter just as much as the agents you're building on top of them. This episode is presented by Workday ~~~ Thank you to our sponsors for making this show possible. Wordsmith.ai Brightflag ~~~ Join Mary's Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts

  6. 12. Mai

    #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 Workday ~~~ Thank you to our sponsors for making this show possible. Wordsmith.ai Brightflag ~~~ Join Mary's Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts

  7. 28. Apr.

    #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 show! Join Mary's Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts

  8. 14. Apr.

    #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 review on Apple Podcasts

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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.

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