
Pearls On, Gloves Off
Smooth operations keep businesses afloat – but what makes them successful? “Pearls On, Gloves Off” is a new podcast where Legal Ops legend Mary O’Carroll and a motley crew of guests share their insider knowledge from running high-performing businesses. Join us for insightful conversations with some of today’s most respected leaders and luminaries.
Latest episodes

Aug 30, 2022 • 47min
#6 - Fergus Speight and Jenny Hacker of Royal London Discuss Legal Ops and Tech in the UK vs. the US
In this episode, Mary is joined by Fergus Speight, General Counsel at Royal London, and Jenny Hacker, Head Of Operations - Legal & CoSec at Royal London, to talk about how they created and innovated a legal ops department before it was an established industry. Fergus explains how he started to see problems in the legal processes at Royal London but lacked the creative thinking to come up with innovative solutions. So he looked to his team and saw Jenny, who has a mind for innovation and the ability to bring ideas to life. Jenny discusses how she came up with ideas for change and how she and Fergus started legal ops in their company long before anyone knew what legal ops was. She explains how they went about making these changes and what they did to make sure that their whole team was on board. To finish off, the pair compare the legal ops industry and tech in the UK with that of the US. If you enjoyed today's show, please leave a 5-star review. You can find more information, as well as the resources mentioned in this episode, at www.ironcladapp.com.

Aug 16, 2022 • 47min
#5 - Deloitte’s Mark Ross Dives Deep Into CLM Technology
In this episode, Mary is joined by Mark Ross, Principal and Co-Leader at Deloitte Legal Business Services, to discuss his impressive career and his best practices in the legal ops space. Mark began his career in England as a personal injury lawyer before emigrating to the US. Here he started his career in legal ops to avoid taking the California Bar Exam. Since then, he has become a powerhouse in the industry. Mark discusses his methods for convincing reluctant leadership to invest in the legal ops side of the business. He details the type of research needed, the information you need to gather, and how to present everything to leadership. Mark also dives into the world of contracts, CLMs, and what can be done to help the contracting process run smoothly. He talks about why it is essential to get as much of it done in-house as possible since contracts are, in his words, touched by everyone and owned by no one. If you enjoyed today’s show, please leave a 5-star review. You can find more information, as well as the resources mentioned in this episode, at ironcladapp.com.

Jul 26, 2022 • 48min
#4 - Dr. Larry Richard Explains Lawyer Personalities and Psychology
In this episode, Mary is joined by her friend Dr. Larry Richard, Founder & Principal Consultant at LawyerBrain LLC, to talk about all things lawyers. Many who work in legal operations, or anywhere dealing with contracts, often feel frustrated by their lawyer colleagues, leading to a lot of bad jokes and poor communication. To help, Larry explains the psychology behind a lawyer’s brain, and why they are the way they are. He then shares ways to communicate with them in a manner that they will respond to more agreeably. Larry breaks down the personality type of a lawyer into qualities both high and low. Where a lawyer is often high in skepticism, autonomy, and problem solving, they are often low in resilience, sociability, and cognitive empathy. Knowing this is key when it comes to understanding what makes a lawyer tick. If you enjoyed today’s show, please leave a 5-star review. You can find more information, as well as the resources mentioned in this episode, at ironcladapp.com.

Jul 12, 2022 • 45min
#3 - Mike Haven Talks About Transitioning From Law Partner to Legal Ops Extraordinaire
In this episode of Pearls On, Gloves Off, Mary is joined by Mike Haven, Senior Director, Associate General Counsel, and Head of Legal Operations at Intel, to talk about how he went from being a partner in a law firm to filling Mary’s shoes as the President of CLOC. Being close friends, Mary and Mike spend some time catching up and raving about the new Top Gun movie before diving into the real conversation. Before becoming a LegalOps extraordinaire, Mike had a very successful career as a partner at a law firm. He talks about finding his passion for LegalOps and how he was able to make the transition. During the pandemic, Mike took over Mary’s position as the President of CLOC, and he tells us how nervous he was to fill Mary’s shoes. He goes on to talk about how he has transitioned CLOC and CLOC events out of the pandemic and brought them offline and back into the real world. If you enjoyed today’s show, please leave a 5-star review. You can find more information, as well as the resources mentioned in this episode, at ironcladapp.com.

Jun 10, 2022 • 42min
#1 - Ironclad’s Alex Su Talks TikTok, Trolls, and Career Changes
In this episode, Mary is joined by Alex Su, Head of Community Development at Ironclad. Alex is somewhat of a celebrity in the legal operations field; his TikTok account @legaltechbro has nearly 75,000 followers. Alex talks about his success on social media, where he gets his ideas, and how he deals with trolls. He goes into detail about the advantages of TikTok versus LinkedIn and explains how the communities on each platform are different. As a former lawyer, Alex’s career hasn’t gone the way he thought it would. He recounts his decision to go from law to legal operations in 2016. Then it was still a new field and he explains how his colleagues questioned his decision. He tells Mary about how he knew it would be a stable career because of talking to people, following trends, and not being afraid of failure. If you enjoyed today’s show, please leave a 5-star review. You can find more information, as well as the resources mentioned in this episode, at ironcladapp.com.

Jun 6, 2022 • 55min
#2 - Director of Legal Operations at Netflix, Jenn McCarron, Breaks Down Her Impressive Career
In this episode, Mary is joined by her long-time friend Jenn McCarron, Director of Legal Operations and Technology at Netflix. The pair discuss Jenn’s career trajectory, the growth of legal ops, and the massively successful CLOC event they attended recently. Jenn takes us through the timeline of her career. Starting from when she was a child and wanted to be a cartoonist all the way to her present role as the director of legal operations at the world’s largest streaming platform. Jenn provides great insight into the benefits of creativity in the legal ops space. She also shares how her own creativity has helped her in her career. Mary and Jenn also walk through the recent, in-person, CLOC event they attended in Las Vegas and discuss what it was that made it such a success. Jenn describes how they filled the Bellagio hotel to capacity with their attendees and Mary goes into detail about how the event moved people to tears. If you enjoyed today’s show, please leave a 5-star review. You can find more information, as well as the resources mentioned in this episode, at ironcladapp.com.

Apr 23, 2022 • 35sec
Welcome to Pearls On, Gloves Off
Smooth operations keep businesses afloat but what makes them successful? Join Mary O’Carroll on her new podcast, Pearls On, Gloves Off, where she is not holding back. Mary is diving into the nitty-gritty of what it takes to run high-performing businesses. Mary will be joined by leaders of some of today’s best high-performing businesses for insightful conversations about what it takes to run one of these businesses. Mary O’Carroll spent 13 years as Director of Legal Operations at Google, 11 years as President at CLOC, and she is now Chief Community Officer at Ironclad. She knows what is necessary to keep a high-performing business running. Mary is a huge advocate of innovation, modernization, and business transformation. She is not afraid to talk about the difficult decisions that are necessary to keep businesses performing at the highest level. If you are not afraid either and want to learn from respected leaders and luminaries, join her by tuning in to this podcast. If you enjoyed today’s show, please leave a 5-star review. You can find more information, as well as the resources mentioned in this episode, at ironcladapp.com.
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