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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
General Counsel
Law Firms
Change Management
Generative AI
Transformation
Ironclad
Goodwin
M&A
Legal Recruiting
Mentorship
Billable Hour
Venture Capital
Leadership
Contracts Lifecycle Management
Legal Services
Compliance
Contract Lifecycle Management

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 monthlyEpisodes93Founded4 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 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

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 ... more

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 shoul... more

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... more

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Recent Guests

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
Mike Abbott
Leads the Thomson Reuters Institute and shapes its research across legal, corporate, tax and accounting.
Thomson Reuters Institute
Episode: #88 - Big Law: Record Profits… For Now
Alex Su
Former litigator, current Chief Revenue Officer at Latitude Legal, known for his comedic content related to the legal profession.
Latitude Legal
Episode: #87 - Updates & Hot Takes with Alex Su
Keir Gumbs
Chief Legal Officer at Edward Jones with over 24 years of experience in law and business, previously held senior positions at Uber and Covington.
Edward Jones
Episode: #85 - Edward Jones CLO Is Moneyball-ing Legal Risk
Jennifer Soltau
Senior Manager of Legal Recruiting at Goodwin
Goodwin
Episode: #83 - Recruiting Gen Z Lawyers in a Broken System

Host

Mary O'Carroll
Host focused on legal ops, technology, and strategy; frequently discusses AI adoption and outside counsel relationships.

Reviews

4.8 out of 5 stars from 44 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.

Guests provide real-world examples, case studies, and honest assessments of AI and tech adoption in legal teams.
The host is commended for asking insightful questions and steering conversations toward actionable outcomes.
Listeners consistently praise high-caliber guest lineups and practical takeaways for legal operations.

Chart Rankings

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Talking Points

Recent interactions between the hosts and their guests.

#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.
#85 - Edward Jones CLO Is Moneyball-ing Legal Risk
Q: How did you go in?
Anytime you come into an organization, you have to start with humility.

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Frequently Asked Questions About This Podcast

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

This show concentrates on how legal services intersect with technology, operations, and business strategy. Episodes frequently explore AI-enabled in-house models, outsourcing versus internal capabilities, modernization of legal departments, and innovative pricing and engagement with outside counsel. Across guests—GCs, CLOs, and senior legal ops leaders—the conversations highlight practical implementations, change management, and the balance between efficiency and high-quality legal judgment. A notable pattern is aligning legal operations with business outcomes, often challenging traditional billable norms and vendor relationships, while showcasing real-world case studies from large organizations across tech, finance, and consumer sectors.

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1. CLOC Talk
2. How I Built This with Guy Raz
3. The Fine Homebuilding Podcast
4. Freakonomics Radio
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this podcast launched 4 years ago and published 93 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. Virginia Briggs
2. Ross McNairn
3. Claire Hart
4. Bill Ryan
5. Ava Guo
6. Mike Abbott
7. Alex Su
8. Keir Gumbs

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