
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

Mar 7, 2023 • 47min
#16 - Humanizing Law Firm Work with Jason Barnwell at Microsoft
On this episode, Jason Barnwell, General Manager for Digital Transformation of Corporate, External, and Legal Affairs at Microsoft, joins Mary to talk about his title. He describes it as being a professional cheerleader, meaning he is creating the vision for the future of the company. The way Jason sees it, law firms are starting to feel pressure to show value. The problem is value is determined by data and resources are needed to generate that data. They can’t show value without the resources. He talks about the difficulty of generating change at a company like Microsoft, and how he has learned to frame the problem from a leadership perspective, not his own perspective. He has learned, over the years, that lawyers are in the feelings business. Decisions are made as much by feeling as by thinking. To get problems solved, you have to humanize the work. Jason Barnwell - https://www.linkedin.com/in/jbarnwell/ 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. #LegalOps #LegalCareer

Feb 21, 2023 • 43min
#15 - Private Practice vs. In-House with Mel Scott of Megaport
On this episode, Mel Scott, Senior Legal Counsel (Global) at Megaport, joins Mary to talk about her career path, which started in private practice and moved quickly to her current in-house role. Mel starts by talking about her podcast: Counsel - A Podcast for In-House Lawyers. One of the reasons Mel started the podcast is to share information and stories that she wished she had access to when she was first starting out in the industry. She spent three years in private practice before taking on an in-house role, and she explains the differences between the two. In her case, she went from a buttoned-up aviation role to the rollercoaster of a tech startup. She discusses the importance of continuously future-proofing your processes in order to increase efficiency and best achieve the vision of the board and executive team. This requires managing what she calls the ‘long tail’ of legal requests. Mel Scott - https://www.linkedin.com/in/theinhouselawyer/ Megaport - https://www.linkedin.com/company/megaport/ 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. #LegalOps #LegalCareer

Feb 7, 2023 • 45min
#14 - Reinventing Law Firm Leadership with Scott Westfahl at Harvard Law School
On this episode, Scott Westfahl, Professor of Practice and Faculty Director of Executive Education at Harvard Law School, joins Mary to talk about his career journey since graduating from Harvard Law School in 1988, including his time at McKinsey and then at Goodwin Proctor before returning to Harvard where he occupies his current post. Scott talks about the importance of feedback for growth in the legal world which is something he learned from the consulting world. This can be either in the moment or at the end of a project, but he believes that feedback and extensive coaching are effective ways to create great leaders. Scott takes us behind the scenes at the Executive Education program at Harvard Law which was launched in 2007 as a leadership development program for senior law firm executives. He talks about his definition of adaptive leadership, a critical skill for legal leadership or legal ops professionals. He also dives into the ways law firms should be embracing experimentation and brainstorming. Scott Westfahl - https://www.linkedin.com/in/scottwestfahl/ Harvard Law School - https://www.linkedin.com/school/harvard-law-school/ 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. #LegalOps #LegalCareer

Jan 24, 2023 • 39min
#13 - A Surprising Love for Procurement with Lesley Garafola at Barings
On this episode, Lesley Garafola, Managing Director, Global Head of Procurement and Vendor Management at Barings, joins Mary to talk about her career history and how it led her to fall in love with procurement, much to her surprise. Lesley began her career at Wells Fargo as a paralegal, with the intention of going to law school. Then she started analyzing data and organically growing the operations side of the legal department and fell into legal ops. Now she heads up procurement, which she finds both fascinating and exciting. The biggest challenge she faced in her transition to procurement was learning how to handle the stakeholders. It takes strategic thinking — an approach she has now instilled in her team. Lesley was personally asked to join procurement. Despite her objections, she finally gave in and is thriving in her field. She takes us through the process and the improvements she and her team have made to the company’s systems and processes, building from the ground up. Lesley Garafola - https://www.linkedin.com/in/lesley-e-garafola-22146210/ Barings - https://www.linkedin.com/company/barings/ 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. #LegalOps #LegalCareer

Jan 10, 2023 • 40min
#12 - Legal Life in the NFL with Jill Kelley of the New York Jets
On this episode, Jill Kelley, VP of Legal Affairs at the New York Jets, joins Mary to talk about the many twists and turns in her career which eventually led to her position with the New York Jets. Something that might surprise people is just how small the legal department is at the Jets. It consists of Jill and a paralegal, so it’s a department of two. As Jill says, it is a highly visible and famous organization but, behind the scenes, the legal department is very much a mom-and-pop operation. Jill's day-to-day work focuses on the business aspect of the franchise. This includes revenue-generating activities like sponsorship agreements, suites and season ticket sales. She also works closely with the multimedia team on broadcast agreements and social media content. Jill talks about being a fan of using technology, usually for contract automation, even though it is a small department. As for the future, the league is focusing heavily on online sports betting, which means data privacy issues are becoming more important every year. Jill Kelley - https://www.linkedin.com/in/jill-kelley/ New York Jets - https://www.linkedin.com/company/newyorkjets/ 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. #LegalOps #LegalCareer

Dec 20, 2022 • 45min
#11 - Being a Legal Ops Pioneer with Reese Arrowsmith of the Campbell Soup Company
On this episode, Reese Arrowsmith, VP, Head of Legal Operations at Campbell Soup Company joins Mary to talk about his career in legal ops that started before legal ops existed. We talk about his time in early legal ops software, long before we called it legal ops. This included selling matter management software in the late 90s and early 2000s and building a system for The Home Depot in 2003 that integrated with the legal department. We also talk about the importance of collaboration and open communication in a legal ops department. This means everyone, from the top down, not being afraid to ask questions or suggest changes when something isn’t working. We also dove into his background as a consultant and the skills he picked up along the way. He says every experience in his varied background has helped him to get to where he is today. Reese Arrowsmith - https://www.linkedin.com/company/campbell-soup-company/ Campbell Soup Company - https://www.linkedin.com/company/campbell-soup-company/ 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. https://ironcladapp.com/ #LegalOps #LegalCareer

Nov 29, 2022 • 43min
#10 - Using Tech for Efficient Legal Ops with Lisa Mango at One Medical
On this episode, Lisa Mango, General Counsel at One Medical, joins Mary to talk about her career journey, through her move to the Bay Area for litigation work, which expanded into an in-house position, to her current role at One Medical today. Now, as a tech-enabled healthcare disruptor, Lisa has to pull on all her experience and knowledge just to deal with the regulations in healthcare that don’t apply to many non-regulated industries. She has done product work, privacy work, transactional law and has spent her whole career expanding her knowledge set as a means of professional development. For example, she did a stint in legal ops, which helped her learn to grow and scale legal departments and has been critical for her career. As she says, she can’t imagine being in her current role as a general counsel without her diverse legal experience. Lisa Mango - https://www.linkedin.com/in/lisamango/ One Medical - https://www.linkedin.com/company/one-medical-group/ 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. #LegalOps #LegalCareer

Oct 26, 2022 • 39min
#9 - Airtable’s Ryan Marks Talks Tech Tools for More Efficient LegalOps
In this episode, Ryan Marks, Head of Legal at Airtable joins Mary to talk about all ways to create an efficient LegalOps department, the importance of data, and how to avoid the reputation as the “Department of No.” Ryan started his career in litigation, working on a variety of different cases over the course of several years. While doing this, he realized that instead of solving problems by working backward with litigation, he wanted to help clients use legal means to avoid those problems in the first place. As the first legal hire at Airtable, Ryan set out to use this approach to create a legal identity for the company from the ground up. He talks about how he and his team are careful to use all available tools to implement processes that will affect both internal and external stakeholders in a way that is comfortable and easy to understand. This approach maximizes growth while minimizing pain. Laying this foundational groundwork has paid off, as the company has grown from 200 to over 1,000 employees and his department has gone from a one-man show to a team of ten specialists. Resource: Ryan Marks: https://www.linkedin.com/in/ryan-marks-4100954b/ 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. https://ironcladapp.com/ #LegalOps #LegalCareer

Sep 27, 2022 • 43min
#8 - General Counsel Shana Simmons Describes Her Impressive Career in Law and LegalOps
On this episode, Shana Simmons, General Counsel at Everlaw, joins Mary to talk about Shana's career journey. From how Shana got a job as a law firm associate in London to why she left that job and moved to California to work as a contract manager at Google. Shana waxes lyrical about her deep love for Google and what it was like to work at a company that was growing so rapidly. She also shares the tools and skills Shana learned at Google and why she didn't learn them as a lawyer, such as building and managing a diverse team. She then goes through how she worked her way up at Google, and why she ultimately left. Lastly, Shana goes into detail about why it's so important to hire talent that is different from you and how to manage them effectively as well as how to use technology to modernize legal operations. Resources: Shana Simmons: https://www.linkedin.com/in/shana-simmons-02295498/ Everlaw: https://www.linkedin.com/company/everlaw/ 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. https://ironcladapp.com/ #LegalOps #LegalCareer

Sep 13, 2022 • 41min
#7 - CLO Extraordinaire Niki Armstrong Talks Optimizing, Automating, Innovating, and Scaling Legal Ops
In this episode, Mary is joined by her friend Niki Armstrong, Chief Legal Officer & Corporate Secretary at Pure Storage, to talk about optimization and innovation in the legal ops space. Niki has had a long and successful career, first as a lawyer and now as a CLO. She runs through her career and how she got to her current position. Then she and Mary walk down memory lane and talk about how their 20-year friendship started at a poorly put-together event in San Francisco. Niki also recounts her time on Richard Branson’s short-lived reality show. She talks about the experience and what she learned from it before sinking her teeth into legal ops. Niki is passionate about legal operations. She shares her approach to innovating processes, optimizing, and automating everything that can be automated while keeping the team on board and free from burnout. 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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