HeyJaredPearls 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.
- Indexed episodes, last 90 days
- 5
- Latest publication
- Sep 1, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 7, 2026
Latest episodes
#102 - Inside Crosby: The AI Law Firm Rethinking How Legal Work Gets Done (opens the original)
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Mary sits down with Ryan Daniels, Co-Founder and CEO of Crosby, for a rare look inside one of legal tech's most talked-about AI native law firms. They dig into why Ryan built a law firm instead of a legal tech company, how fixed fee pricing completely changes the unit economics of legal services, why Crosby lawyers are evaluated on speed not hours, how they're building a data moat from every contract they touch, and what it actually looks like when a law firm is designed from day one to hand wor
#101 - Ford's Warning Shot: Adapt or Get Left Behind (opens the original)
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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 native firms still have a trust problem, and what the legal department of the future really needs to
#100 - The Future of Legal Is Already Here - A Conversation with CLO Eric Greenberg (opens the original)
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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 relationships, and why the most important leadership skill right now is making it okay to be wrong. This episode
#99 - Who Is Sandstone? Inside Legal Tech's Most Talked-About Company (opens the original)
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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
#98 - Anna Richards (opens the original)
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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 ma
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