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Artwork for Pearls On, Gloves Off: The Legal Innovation Podcast

Pearls On, Gloves Off: The Legal Innovation Podcast

Mary O'Carroll
Legal Operations
Artificial Intelligence
Legal Technology
Law Firms
General Counsel
Change Management
Generative AI
Transformation
Ironclad
Goodwin
M&A
Legal Recruiting
Mentorship
Billable Hour
Venture Capital
Leadership
Legal Innovation
Contracts Lifecycle Management
Legal Services
Compliance

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.

PublishesTwice monthlyEpisodes96Founded4 years ago
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Artwork for Pearls On, Gloves Off: The Legal Innovation Podcast

Latest Episodes

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 design... more

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 a... more

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 t... more

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.

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Thank you to our spon... more

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Recent Guests

Michael Pierson
Co-Chairman, Pierson Ferdinand
Pierson Ferdinand
Episode: #94 - Who Needs Associates? Pierson Ferdinand's Partner Only Model
Joel Ferdinand
Co-Chairman, Pierson Ferdinand
Pierson Ferdinand
Episode: #94 - Who Needs Associates? Pierson Ferdinand's Partner Only Model
Christina Wojcik
Chief Innovation Officer, Pierson Ferdinand
Pierson Ferdinand
Episode: #94 - Who Needs Associates? Pierson Ferdinand's Partner Only Model
Winston Weinberg
CEO of Harvey
Harvey
Episode: #93 - Harvey CEO: Individual Productivity Is a Trap
Virginia Briggs
CEO and managing partner of MinterEllison (Australia)
MinterEllison
Episode: #92 - "AI is our Kodak Moment"
Ross McNairn
Founder and CEO of Wordsmith, AI command center for in-house legal teams
Wordsmith
Episode: #91 - CEO: 70% of Legal Tech Gone by 2027
Claire Hart
Chief Operating Officer, Chief Legal Officer and board member at Groq
Groq
Episode: #90 - Clients "Do Their Own Research." That's A Problem for Law Firms
Bill Ryan
Senior Vice President and Chief Compliance Officer at AT&T
AT&T
Episode: #89 - AT&T's New In House Law Firm
Ava Guo
AVP and Senior Legal Counsel at AT&T, leading e-discovery and legal technology
AT&T
Episode: #89 - AT&T's New In House Law Firm

Host

Mary O'Carroll
Host of Pearls On Gloves Off: The Legal Innovation Podcast; COO at Goodwin; sponsor-related involvement with Workday

Reviews

4.8 out of 5 stars from 47 ratings
  • Great Content for any Legal Ops Professional

    Mary always provides insightful content for which I am eagerly awaiting to learn with each podcast. I learn so much and receive the reinforcement needed to become a better Legal Ops professional. Thank you Mary!!

    Apple Podcasts
    5
    St Johns CR210
    United States3 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Listeners describe high-quality, actionable insights on legal tech and AI adoption.
Guests are seen as leading voices in legal operations and AI-enabled transformation.
The host is praised for practical perspectives and initiative examples.
The show is valued for real-world ROI and governance discussions.
Sponsorships are viewed as well-integrated into meaningful conversations.

Chart Rankings

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Talking Points

Recent interactions between the hosts and their guests.

#94 - Who Needs Associates? Pierson Ferdinand's Partner Only Model
Q: Are these equity partners, and do they do work traditionally done by associates?
The firm operates with two general partners and a partner-only structure where partners handle work that would typically involve associates, using AI to draft and speed up work while senior lawyers review for quality and accuracy.
#91 - CEO: 70% of Legal Tech Gone by 2027
Q: How does Wordsmith interact with in-house teams and what makes it different from traditional external counsel tools?
Wordsmith acts as an infrastructure and control center that enables supervised self-service for legal, reduces noise and external spend, and provides auditable context and governance for corporate legal activities, effectively acting as an internal AI brain for the business.
#91 - CEO: 70% of Legal Tech Gone by 2027
Q: Why does anybody want to become a founder in the legal tech space given the crowded and exhausting nature of the field?
The guest explains that for him, the core drive is building and shaping things, enjoying the process of designing and iterating, and finding fulfillment in creating tools that improve how businesses operate, despite the risks and demands of entrepreneurship.
#87 - Updates & Hot Takes with Alex Su
Q: What do you think about the rise of ALSPs?
ALSPs are positioning themselves alongside traditional law firms, providing essential services while offering diverse paths for legal professionals.
#87 - Updates & Hot Takes with Alex Su
Q: What makes legal tech adoption so hard?
Legal tech adoption is challenging because simply buying AI does not equate to effective usage. Integration into daily workflows is essential for realization of its value.

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Frequently Asked Questions About This Podcast

What is This Podcast about and what kind of topics does it cover?

The show leans into the intersection of law, technology, and new operating models for legal teams. Across episodes, the conversation centers on AI-native workflows, in-house centers of excellence, innovative pricing, and governance frameworks that enable faster, more transparent legal services while balancing judgment and risk. Sponsors and real-world deployments (e.g., Workday, Bright Flag) frame practical AI adoption, governance, and measurement of value in large organizations. A standout theme is the shift from traditional firm models toward technology-enabled, client-value-driven delivery, with a strong emphasis on governance, data quality, and talent strategy. Potential listeners should be drawn to high-level strategy discussions from ... more

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this podcast launched 4 years ago and published 96 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on this podcast?

Recent guests on this podcast include:

1. Michael Pierson
2. Joel Ferdinand
3. Christina Wojcik
4. Winston Weinberg
5. Virginia Briggs
6. Ross McNairn
7. Claire Hart
8. Bill Ryan

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