Pearls On, Gloves Off: The Legal Innovation Podcast – Details, episodes & analysis

Podcast details

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Pearls On, Gloves Off: The Legal Innovation Podcast

Mary O'Carroll

Business

Frequency: 1 episode/16d. Total Eps: 100

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.

Recent rankings

Latest chart positions across Apple Podcasts and Spotify rankings.

Apple Podcasts

🇨🇦 Canada - management
10/08/2026
#89
🇨🇦 Canada - management
31/07/2026
#62
🇨🇦 Canada - management
24/07/2026
#87
🇬🇧 Great Britain - management
24/07/2026
#62
🇨🇦 Canada - management
23/07/2026
#46
🇬🇧 Great Britain - management
21/07/2026
#83
🇨🇦 Canada - management
14/07/2026
#79
🇨🇦 Canada - management
13/07/2026
#67
🇺🇸 USA - management
12/07/2026
#96
🇨🇦 Canada - management
26/06/2026
#86

Spotify

No recent rankings available

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RSS feed quality and score

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RSS feed quality

Good

Score global : 73%

Publication history

Monthly episode publishing history over the past years.

Year

Latest published episodes

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#53 - Building the Law Firm of the Future: A Conversation with Goodwin's Leaders

Episode 53

Tuesday, October 8, 2024 • Duration 42:43

Welcome to another episode of Pearls On, Gloves Off with your host, Mary O'Carroll, Chief Operating Officer at Goodwin. Today, Mary sits down with Goodwin's leaders—Anthony McCusker, Chair, and Mark Bettencourt, Managing Partner—for an insightful conversation about the firm's unique culture, its client-centric approach, and the future of the legal industry.

Anthony McCusker is widely recognized as a preeminent adviser in corporate securities and partnership laws, with a primary focus on advising technology companies and their investors. He chairs the firm's Executive Committee and is a member of its Management Committee and Allocations Committee.

Mark Bettencourt has extensive experience in mergers and acquisitions, public offerings, private placements of debt and equity securities, securities law compliance, and technology transfer and licensing. He chairs the firm's Management and Allocations Committees and serves on the Executive Committee.

In this episode:

Embracing a Unique Culture: Mary's early observations about Goodwin's collaborative, team-first attitude and what sets the firm apart.
Forward Thinking Innovation: How Goodwin is driving change in the industry through novel solutions, technology, and AI that enhance client service.
Client-Centric Approach: The importance of being deeply immersed in clients' industries and providing holistic business advice beyond traditional legal services.
The Changing Role of Legal Professionals: How the role of general counsel is evolving and what that means for law firms and lawyers.
Building for the Future Generation: The significance of mentorship, apprenticeship, and providing lawyers with the tools and opportunities to thrive.
The Power of Collaboration: The results of working together across all levels of the firm to achieve common goals and drive success.

We hope you enjoy this engaging conversation that offers a glimpse into the future of law firms and how Goodwin is embracing change to better serve clients and support its people.

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#52 - From Improv to AI: HubSpot CLO Alyssa Harvey Dawson

Episode 52

Tuesday, September 24, 2024 • Duration 42:41

Welcome to another episode of Pearls On, Gloves Off with your host, Mary O'Carroll, Chief Operating Officer at Goodwin. After a brief hiatus, we're back, and this episode features a fascinating conversation with Alyssa Harvey Dawson, Chief Legal Officer at HubSpot.

With over 20 years of experience leading legal teams at major companies like Gusto, Sidewalk Labs, Netflix, and Autodesk, Alyssa shares her insights on navigating AI challenges, the evolving role of legal leadership, and what it takes to build strong legal operations in today's complex, tech-driven landscape.

In this episode:

· The evolving role of general counsel as a strategic partner in business growth.

· The importance of trust and data governance in legal teams' approach to AI.

· The challenges of balancing global regulations, customer expectations, and innovation.

· Building a legal team that fosters business alignment and addresses customer needs.

· Insights into HubSpot's legal operations and their approach to managing AI, compliance, and data security.

· Alyssa's thoughts on the skills needed to succeed in today's legal operations roles, including business judgment and adaptability.

· The unexpected benefits of improv in developing leadership skills in a corporate setting.

Enjoyed this conversation? Don't forget to subscribe to Pearls On, Gloves Off for more insightful discussions with leading figures in the legal and corporate sectors. Share your thoughts and join the conversation on our social media channels.

Follow Mary on LinkedIn

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#43 - Creating Buy-In and Driving Efficiency with Anna Richards

Episode 43

Wednesday, May 8, 2024 • Duration 47:58

In this episode of Pearls On, Gloves Off, Mary O'Carroll sits down with Anna Richards, Director of Global Legal Operations at John Deere. With over 15 years of experience, Anna brings deep insights from companies like Autodesk, Zendesk, and Micron Technology.Mary and Anna dig into:

Transitioning to John Deere: Anna details her onboarding journey, where Deere laid the groundwork by first understanding the role of legal operations and investing in its success.
Unique Challenges: As one of the few remote employees, Anna shares the importance of relationship-building and progress-making despite her unique work arrangement.
Diverse Roles: Anna reflects on her legal ops journey across different companies, sharing how no two roles are the same and how each experience is valuable.
Technology in Legal Ops: They discuss how John Deere aims to become a tech-forward company, targeting 10% recurring revenue by 2030. This requires significant investments in tech tools and IT partnerships.
Setting Up Success: Mary highlights the necessity of strategic hiring and the importance of investment in support, vendors, tech, and tools.
Creating Buy-In: Anna talks about Deere's strategic approach to building the legal ops function, conducting surveys to identify opportunities and building a business case for stakeholder buy-in.
Current Projects: From implementing an enterprise-wide CLM system to aiming for 50,000 hours saved by 2026, Anna shares her ambitious goals and hiring plans.

Follow Us and Stay Connected:

Follow Mary on LinkedIn: Mary's LinkedIn
Follow Ironclad on LinkedIn: Ironclad LinkedIn
Watch Ironclad on YouTube: Ironclad YouTube
Check out Ironclad on TikTok: Ironclad TikTok
Rate and review on Apple Podcasts:

linkedin.com Please reach out if I can be helpful at all. I love to provide (free!) advice on scaling… · Experience: Ironclad, Inc. · Location: San Francisco Bay Area · 500+ connections on LinkedIn. View Mary O'Carroll's profile on LinkedIn, a professional community of 1 billion members. linkedin.com Ironclad | 27,926 followers on LinkedIn. Ironclad is the smart way to make and manage digital business contracts. Now powered by Ironclad AI. | Ironclad is the #1 contract lifecycle management platform for innovative companies, powering billions of contracts every year. L'Oréal, Salesforce, OpenAI and other leading innovators use Ironclad to collaborate and negotiate on contracts, accelerate contracting while maintaining compliance, and turn contracts into critical carriers of operational business intelligence. It's the only platform flexible enough to handle every type of contract workflow, whether a sales agreement, an HR agreement or a complex NDA. YouTube Ironclad is the digital contract platform loved by modern business teams.Contracts are business decisions trapped in administrative tasks. Ironclad is software that does all the administrative work better left for a computer, freeing teams -- legal, sales, procurement, finance, HR, etc -- to do substantive work and drive business strategy.We believe contracts should be business assets. Some document management vendors focus on contracts as risk assets: documents that, when poorly managed, expose companies to significant, surprising risks. While not knowing what's in your contracts can certainly be dangerous, we prefer to focus on the valuable intelligence you can extract from them to drive… Show more Apple Podcasts

#42 - Strategic Solutions: Navigating Legal Operations Challenges with Dawn Hinz

Episode 42

Wednesday, April 24, 2024 • Duration 43:48

In this episode of "Pearls On, Gloves Off," Mary sits down with Dawn Hinz, legal operations leader at Avery Dennison. Together, they dive into the nuances of leading and transforming the legal ops landscape. In The Episode:

Exploring Strategy and Improvement: Dawn's role at Avery Dennison: strategy development, process enhancement, and resource optimization. She shares her methodologies in change management and the hurdles faced during large-scale tech implementations.
Cultivating Success: The critical elements that foster a successful legal operations function—supportive culture, robust leadership, and the essential skills needed. Dawn discusses her approach to team building and the traits she values in potential hires.
Overcoming Resistance: The common challenges of introducing new systems within firms and how to effectively manage resistance to change. The significance of being a proactive change agent equipped with strategic and program management prowess.
Lessons from Dell: Dawn reflects on her tenure at Dell, discussing the evolution of legal operations and the importance of a comprehensive understanding of business processes. They discuss striking the right balance between mitigating risks and maintaining operational efficiency.
Demonstrating Value: They emphasize the ongoing need to support legal operations and ways to showcase its impact. Dawn offers her personal advice for aspiring legal ops professionals, urging them to embrace leadership roles, seize learning opportunities, and initiate change.

Connect with Us:

Follow Mary on LinkedIn: Mary O'Carroll
Follow Ironclad on LinkedIn, YouTube, and TikTok

Support the Podcast:

Love the show? Rate and review us on Apple Podcasts. Your feedback helps us grow and reach new listeners!

#41 - Breaking Glass and Taking Risks: Charlene Barone on Leadership in Legal Operations

Episode 41

Wednesday, April 10, 2024 • Duration 47:12

In this episode of Pearls On, Gloves Off, Mary O'Carroll welcomes the formidable Charlene Barone, currently steering the ship as the Director of Legal Operations at the New York Times. Charlene, with her rich history traversing from contracts manager to legal ops leader, brings a wealth of knowledge from both the startup world and the franchise legal landscape of Orange Theory Fitness.

A Tale of Two Worlds: Mary and Charlene explore the contrasts and challenges f@aced in the legal departments of Orange Theory and the New York Times, highlighting the critical role of general counsel in championing innovation.
Strategic Moves: Charlene opens up about the strategic initiatives that have marked her career, offering golden nuggets of advice for those aspiring to climb the legal ops ladder.
The Brave Leap: From Contracts Manager to Legal Ops Director, Charlene's journey is a masterclass in risk-taking and the indispensable support of a general counsel.
Foundation in Contract Management: Charlene credits her rigorous experience in contract management as the bedrock of her success, encouraging newcomers to start their legal ops journey there.
Initiative and Innovation at Orange Theory: Charlene reflects on her tenure at Orange Theory, emphasizing the impact of supportive general counsel on her ability to implement transformative projects, like a Contract Lifecycle Management system.
Strategy at The New York Times: With a larger team and more resources, Charlene shares her strategic priorities and the open, supportive environment that fosters innovation at the New York Times.
The GC Partnership: The significance of a solid relationship with general counsel, the courage to take risks, and the importance of communication are underscored.
Continuous Improvement: Charlene motivates legal ops professionals to seize opportunities for enhancement, advocating for small starts leading to major leaps.

Stay connected and dive deeper into the world of legal operations by following us:

Follow Mary on LinkedIn
Follow Ironclad on LinkedIn, YouTube, and

#40 - The Magic of Curiosity, with Chris Clearfield

Episode 40

Wednesday, March 27, 2024 • Duration 47:27

In this episode of Pearls On, Gloves Off, Mary O'Carroll sits down with Chris Clearfield, a true trailblazer in the world of leadership and management. As the CEO of Clearfield Group and the co-author of "Meltdown," Chris brings a fresh take on how to lead through the chaos and complexity of today's business landscape.

Change Leadership, Not Management: Mary and Chris dig into why "change management" just doesn't cut it. Chris suggests we need to shift our focus to "change leadership" - guiding people through the unknown, tackling fear head-on, building trust, and creating a space where ideas can flow freely.
The Legal Industry's Slow Dance with Change: The conversation takes a turn towards the legal sector's sluggish pace when it comes to adapting to change. Mary sheds light on the crucial role of legal operations and why professionals need to step up and become strategic leaders.
Beyond the Business Case: Chris challenges the conventional wisdom of relying solely on data to drive change. He emphasizes the importance of empathy, listening, and really engaging with people to understand their concerns and aspirations.
A Blueprint for Change: The duo dives into Chris's model for leading change, from recognizing the challenge to achieving and moving beyond the desired outcomes. They discuss how resistance is inevitable and why it's smart to focus on those who are on the fence about change rather than the die-hard resistors.
Cultivating Willingness: Mary and Chris explore the power of starting small, with willing groups, to spark change across an organization. They share inspiring stories of how small beginnings can lead to big transformations, creating a ripple effect of engagement and acceptance.

This episode is a gold mine for leaders, change-makers, and anyone looking to navigate the choppy waters of transformation with grace and impact.Connect with Us:

If you liked this episode, we'd be grateful for your ! linkedin.com Please reach out if I can be helpful at all. I love to provide (free!) advice on scaling… · Experience: Ironclad, Inc. · Location: San Francisco Bay Area · 500+ connections on LinkedIn. View Mary O'Carroll's profile on LinkedIn, a professional community of 1 billion members. linkedin.com Ironclad | 26,262 followers on LinkedIn. Ironclad is the smart way to make and manage digital business contracts. Now powered by Ironclad AI. | Digitize your contracts with Ironclad, the world's #1 Contract Lifecycle Management (CLM) platform. Ironclad is the simple, secure way to create and collaborate on contracts, giving users an all-in-one, AI-powered experience.Every company runs on contracts, but managing these contracts slows companies down and costs them millions of dollars. YouTube Ironclad is the digital contract platform loved by modern business teams.Contracts are business decisions trapped in administrative tasks. Ironclad is software that does all the administrative work better left for a computer, freeing teams -- legal, sales, procurement, finance, HR, etc -- to do substantive work and drive business strategy.We believe contracts should be business assets. Some document management vendors focus on contracts as risk assets: documents that, when poorly managed, expose companies to significant, surprising risks. While not knowing what's in your contracts can certainly be dangerous, we prefer to focus on the valuable intelligence you can extract from them to drive… Show more Apple Podcasts

#39 - Mary's Guide to CLM

Episode 39

Wednesday, March 13, 2024 • Duration 01:06:38

In this solo episode, Mary O'Carroll shares her insights on Contract Lifecycle Management (CLM). She explores:

The Challenges of Contracts: Overview of common issues in contract processes and the potential for improvement.
Ownership of CLM: Advocates for General Counsel to lead CLM processes, highlighting the strategic value of contracts data.
Evolution of CLM Technology: From basic database systems to modern, comprehensive CLM solutions that facilitate collaboration and integration.
Selecting a CLM Vendor: Tips on navigating the CLM market, the role of AI in CLM, and strategies for adoption.
Implementation Strategies: Advice on aligning stakeholders, scoping requirements, and launching a successful CLM project.
The Future of Contract Management: The impact of AI on CLM, improving processes, and unlocking business insights.

Connect with Us:

Follow Mary on LinkedIn: Mary O'Carroll

Stay Updated with Ironclad:LinkedIn
YouTube
TikTok

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Pearls On, Gloves Off: The Legal Innovation Podcast – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

Shared links between episodes and podcasts

RSS feed quality and score

Publication history

Latest published episodes

Related Shows Based on Content Similarities

Related Shows Based on Content Similarities

Apple Podcasts

Spotify

Pearls On, Gloves Off: The Legal Innovation Podcast – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

Shared links between episodes and podcasts

LinkedIn53

Apple Podcast3

Other12

RSS feed quality and score

Publication history

Latest published episodes

Similar podcasts and content

Related Shows Based on Content Similarities

Related Shows Based on Content Similarities

Apple Podcasts

Spotify

LinkedIn53

Apple Podcast3

Other12