Podcast artwork thumbnail for Pearls On, Gloves Off: The Legal Innovation Podcast

Pearls On, Gloves Off: The Legal Innovation Podcast

Mary O'Carroll

Booking Overview

This interview-led legal innovation show focuses on legal services, legal technology, and the transformation of corporate legal departments, with recurring conversations featuring General Counsels, Chief Legal Officers, legal operations leaders, and legal technology founders. Credible pitch candidates include senior in-house legal executives, legal operations innovators, and founders leading consequential legal technology or AI-driven law firms; booking difficulty is high because guests typically hold prominent leadership roles and bring substantial organizational or industry authority.

Metrics

Episodes: 106

Frequency: Every two weeks

Rating: 4.7/5.0

Estimated listeners: 100 - 1,000

Listener location: USA

YouTube: 48 subscribers

Contact Information

Publicly listed emails

john.weeke@ironcladhq.com

Looking for the right person? Join Podseeker to find direct host and producer contacts and manage your podcast outreach.

Host

Mary O'Carroll - Legal operations and legal innovation executive known for her leadership in legal operations at Google and her work advancing legal technology and modern legal departments.

Booking Intelligence

Booking Requirements

high
Typical Credentials:  
General Counsels, Chief Legal Officers, senior legal operations executives, founders and CEOs of significant legal technology companies, and leaders with direct experience transforming legal services.
Required Achievements:  
Leading a major corporate legal department, Driving legal operations or technology transformation, Founding or scaling a legal technology or AI-focused company, Developing new approaches to legal services delivery

Recent Guest Discussions

Ryan Daniels - Ai-native Law Firms, Fixed-fee Pricing, Legal Services Economics, Lawyer Performance, Contract Data, And Agent-enabled Legal Work.

Darth Vaughn - Modernizing Corporate Legal Departments, Outside Counsel Expectations, Billable-hour Alternatives, Ai-native Firms, Trust, And The Future Of Legal Operations.

Eric Greenberg - Leading Legal Department Transformation, AI Governance, Legal Technology Adoption, Outside Counsel Relationships, And Leadership.

Nick Fleisher - Legal Technology, Ai-native Teams, Software Development, Permissions And Context In In-house Legal Work, And Lean Company Building.

Anna Richards - Legal Operations Leadership, Evolving Skill Requirements, Legal Technology Stacks, And Rising Expectations For Legal Operations Teams.

Recent Topics

Legal Innovation, Legal Technology, Legal Operations, Artificial Intelligence, Legal Services

Episodes

Here's the recent few episodes on
Pearls On, Gloves Off: The Legal Innovation Podcast
:

#105 - Disrupt Yourself First: How Redgrave Is Rebuilding the Law Firm Model

October 13, 2026

Mary sits down with Erica Zolner, Britney Colton, and Ray Mangum of Redgrave LLP, an information law firm that runs nothing like a traditional firm. They dig into what happens when lawyers and technologists work side by side, how AI turned 600,000 contract PDFs into a risk picture in five days, why disrupting yourself beats waiting to be disrupted, why clients still hold on to the billable hour, and how real-time feedback shapes how the firm rewards its people. This episode is presented by PL...

#104 - Flight Simulators for Lawyers: The Rise of the Legal Engineer and How the Profession Learns

September 29, 2026

Mary sits down with Stanford Law's Adam Sterling and Irene Liu to unpack the school's new Legal Engineering Academy. They dig into what a legal engineer actually is, why the legal apprenticeship model has been broken for years, how AI-powered 'flight simulators' could compress a decade of experience into months, why AI may be pushing demand for young lawyers up rather than down, and what the legal talent ecosystem could look like ten years from now. This episode is presented by Workday. Join ...

#103 - The Lawyer Personality Unpacked: What the Data Says After 32 Years of Research

September 15, 2026

Mary sits down with Dr. Larry Richard, psychologist, former lawyer, and the foremost researcher on lawyer personality, for a return visit that goes even deeper than their first conversation. They dig into the seven personality traits that make lawyers uniquely wired for the law and uniquely challenged by everything else, why nine out of ten lawyers are thin-skinned, why empathy has dropped 50% in the last twelve years, what that means for legal leadership in an AI-driven world, and what the s...

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Pearls On, Gloves Off: The Legal Innovation Podcast
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Technically Legal - A Legal Technology and Innovation Podcast · Medium booking difficulty · 100 - 1,000 listeners

Frequently asked questions

Here's some frequently asked questions for
Pearls On, Gloves Off: The Legal Innovation Podcast
:

How do I get in touch with Pearls On, Gloves Off: The Legal Innovation Podcast?

Pearls On, Gloves Off: The Legal Innovation Podcast is hosted by Mary O'Carroll. Its publicly listed email is john.weeke@ironcladhq.com. For guest bookings, the host or producer is usually the best person to reach. Podseeker helps you find direct host and producer contacts and pitch from your own inbox.

What is the email for Pearls On, Gloves Off: The Legal Innovation Podcast?

The publicly listed email for Pearls On, Gloves Off: The Legal Innovation Podcast: john.weeke@ironcladhq.com.

How many listeners does Pearls On, Gloves Off: The Legal Innovation Podcast have?

Podseeker estimates Pearls On, Gloves Off: The Legal Innovation Podcast reaches 100 to 1,000 listeners per episode. Only the publisher has exact numbers.

Who is an ideal guest for Pearls On, Gloves Off: The Legal Innovation Podcast?

Pearls On, Gloves Off: The Legal Innovation Podcast typically books industry leaders. Typical guest background: General Counsels, Chief Legal Officers, senior legal operations executives, founders and CEOs of significant legal technology companies, and leaders with direct experience transforming legal services. Common among recent guests: Leading a major corporate legal department; Driving legal operations or technology transformation; Founding or scaling a legal technology or AI-focused company. Recent guests include Ryan Daniels, Darth Vaughn, and Eric Greenberg.

How hard is it to get booked on Pearls On, Gloves Off: The Legal Innovation Podcast?

High. It mostly books established leaders in its field.

What topics does Pearls On, Gloves Off: The Legal Innovation Podcast cover?

Recent episodes cover Legal Innovation, Legal Technology, Legal Operations, Artificial Intelligence, and Legal Services. Pitch an idea tied to one of these topics and mention a recent episode.

Publicly listed emails

john.weeke@ironcladhq.com

Looking for the right person? Join Podseeker to find direct host and producer contacts and manage your podcast outreach.

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