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

  “Sometimes the right answer for Anthropic would be things that 99% of tech companies wouldn’t even consider. You have to be appropriately open to weirdness—not weirdness for the sake of weirdness, but tied to what we’re trying to achieve in the world.” —Brian Isreal, GC, Anthropic In this episode, Mary sits down with Brian Israel, General Counsel at Anthropic, to explore what it’s like to operate at the legal and cultural frontier of AI. From building a hypergrowth legal team to designing a legal “front end” that prioritizes user experience, Brian shares his perspective on leadership, innovation, and navigating the edge of the possible. Topics covered include: Anthropic’s mission: Building a safer transition to transformative AI and how that shapes the company's operations and values. Legal team culture: What it means to be “appropriately open to weirdness” in service of a larger mission. Hypergrowth dynamics: Lessons from scaling a legal team from one person to 27 in just two years. Front-end legal design: Translating complex legal concepts into actionable advice for fast-moving teams. AI in legal workflows: How Anthropic’s own tool, Claude, has become an integral member of the legal team. Ownership and leadership: Why accountability and agency are critical in a high-stakes environment. Brian’s journey to Anthropic—from NASA to startup land—is as unconventional as his approach to law. Tune in to hear his insights on culture, collaboration, and why the best legal teams are both technically excellent and human-centered. Catch the full conversation now, and don’t miss Brian’s take on how AI is poised to redefine the legal profession. Connect with us and join the conversation: Follow Mary on LinkedIn Rate and review on Apple Podcasts  

This special episode was recorded live at Goodwin's Tech Retreat in San Francisco, where Mary sits down with Phil Mazzara, General Counsel of Astera Labs, to explore the evolving role of the general counsel in today's rapidly changing technological landscape. Phil's journey is nothing short of extraordinary. Before becoming an attorney, he spent over a decade on active duty as a Navy pilot, bringing a unique perspective to the legal field. With a JD/MBA from Stanford, Phil skipped the traditional law firm route and went straight in-house. Prior to joining Astera Labs, he served as General Counsel and Secretary at Innovium, where he oversaw multiple venture financings, negotiated critical commercial agreements, settled bet-the-company litigation, built a robust IP portfolio, and ultimately led the company through its $1.1 billion acquisition by Marvell Technology. At Astera Labs, Phil played a pivotal role in taking the company public in March 2023, a challenging year for capital markets. Under his legal guidance, Astera Labs has been riding the AI wave, focusing on AI infrastructure and experiencing significant growth. In this engaging live conversation, Phil and Mary delve into: ·         The Journey to IPO: Phil shares his experiences taking Astera Labs public in a tough market, the importance of choosing the right outside counsel, and how Goodwin played a crucial role in their successful IPO. ·         AI in Legal Practice: How AI is impacting the legal profession, both within corporate legal departments and in law firms, and the potential future applications of AI in complex legal work. ·         The Evolving Role of General Counsel: Discussing how the general counsel's role has expanded beyond traditional legal services to include compliance, business strategy, and being a key advisor to the executive team. ·         Building Strong Law Firm-Client Relationships: Phil offers advice to law firms on how to better serve their clients, emphasizing the importance of understanding the client's business deeply, being proactive, and building trust. ·         Quality of Legal Work and Service: How to measure and ensure high-quality legal services, the significance of responsiveness, attention to detail, and open communication. ·         Advice for Junior Lawyers: The value of seeking opportunities to engage directly with clients, asking questions to understand their business, and stepping up to deliver work product in front of senior executives. ·         Leadership Lessons from the Navy: Phil reflects on how his experience as a Navy pilot informs his approach to leadership, project management, and the use of checklists to ensure quality and reduce errors. ·         The Future of Legal Practice: A candid discussion on how AI and technological advancements are shaping the legal industry, the enduring importance of judgment and counsel, and the skills lawyers will need to succeed in the future. If you're interested in the intersection of law, technology, and business—or if you're curious about how military experience can translate into corporate leadership—this live episode is a must-listen. Connect with us and join the conversation: Goodwin Exhibit A Follow Mary on LinkedIn Rate and review on Apple Podcasts  

Welcome to another episode of Pearls On, Gloves Off with your host, Mary O’Carroll, Chief Operating Officer at Goodwin. Today, Mary dives deep with Chris Grant, Head of Legal Market Engagement at HSBC, to unravel the evolving landscape of the legal industry. Chris Grant isn’t your typical legal professional. Frustrated by the glacial pace of change in an industry resistant to innovation, Chris has spent his career challenging the status quo. From his early days in private practice to his current role at HSBC, he’s been a relentless advocate for efficiency and transformation in legal services. He’s built ecosystems supporting next-generation legal solutions, notably at Barclays Eagle Labs, and has been recognized in the Financial Times Innovative Lawyers Top 10 Entrepreneurs and the Legal 500 GC Power List. In this episode: ·         The Frustration That Fuels Change: Chris shares how his early career disillusionment ignited a passion for legal transformation. ·         Is Change Finally Happening? A candid discussion on whether the legal industry is genuinely evolving or just paying lip service. ·         The Death of the Billable Hour: Will we ever see it? Chris offers a provocative take on alternative fee arrangements—or as he calls them, Effective Fee Arrangements (EFAs). ·         Trust Issues: Delving into the often-unspoken lack of trust between clients and firms, and how it hinders progress. ·         Data as the New Gold: How leveraging data can revolutionize legal services, from pricing to service delivery. ·         Advice for In-House Teams and Firms: Practical steps both sides can take to build trust, embrace innovation, and deliver real value. ·         The Role of Technology: Why AI is more than just a buzzword and how it’s accelerating conversations that were stagnant for decades. ·         Future Gazing: Chris’s vision for the next 5-10 years in legal services, and why he believes the time for change is now. If you’re as passionate about legal transformation as Mary and Chris, or just curious about the seismic shifts shaking up the industry, this episode is a must-listen. Follow Mary on LinkedIn Rate and review on Apple Podcasts

Welcome to another episode of Pearls On, Gloves Off with your host, Mary O’Carroll, Chief Operating Officer at Goodwin. In this episode, Mary sits down with Reena SenGupta, a longtime analyst, writer, consultant, and thought leader in the global legal industry with almost 30 years of experience. Reena’s journey is impressive. She is an entrepreneur and journalist who has developed some of the most influential rankings and programs in the legal world. She was instrumental in creating the Chambers and Partners Guides in the mid-90s and the Financial Times Innovative Lawyers Program, which is about to celebrate its 20th anniversary. In 2001, Reena founded RSG Consulting, which quickly became a leading brand in the legal sector. Today, she heads up RSGI, a global think tank focused on building a sustainable future for the legal industry. Reena is also a seasoned public speaker and regular contributor to the Financial Times, always bringing fresh, forward-thinking perspectives to the table. In this episode: ·         The Changing Legal Landscape: Exploring how the legal industry has evolved over the past two decades, including shifts in mindset and practice. ·         Defining Innovation in Law: Discussing what innovation truly means in the legal context and how it’s being implemented in firms and legal departments. ·         The Impact of Generative AI: Examining how generative AI is transforming legal work, from automating routine tasks to enabling lawyers to focus on strategic, high-value activities. ·         The Future Role of Lawyers: Insights into what the lawyer of tomorrow looks like, including the skills and roles that will be essential in a changing industry. ·         Client Expectations and Pressures: Understanding what’s driving client expectations and how law firms can better meet their clients’ evolving needs. ·         Challenges and Opportunities: Addressing the obstacles holding back the industry and the exciting opportunities for growth and transformation. ·         Reena’s Predictions: Reena shares her predictions for the next 12 months and beyond, including the potential for law firms to become masters of their own data. If you enjoyed our conversation with Reena SenGupta, be sure to subscribe to Pearls On, Gloves Off for more candid discussions with leaders shaping the legal and corporate landscape. We’d love to hear your thoughts—connect with us on social media and join the conversation! Follow Mary on LinkedIn Rate and review on Apple Podcasts  

Welcome to another episode of Pearls On, Gloves Off with your host, Mary O’Carroll, Chief Operating Officer at Goodwin. In this episode, Mary sits down with Joe Hyrkin, Chief Executive Officer of Issuu, a leading digital publishing platform that’s transformed how content is shared and consumed online. With over 30 years of experience in startup and growth technology leadership across Silicon Valley, New York, Asia, and Europe, Joe brings a wealth of knowledge from early-stage ventures to IPOs and successful exits. Under his 11-year leadership at Issuu, the company expanded its product offerings, increased revenue and profitability, forged partnerships with industry giants like Canva, Adobe, and HubSpot, and achieved a nine-figure exit in a challenging M&A landscape. In this episode: Navigating a Successful Exit: How Joe led Issuu to a nine-figure sale during a slow year for M&A and capital markets. Flexibility and Resilience: The importance of adaptability in leadership amidst unpredictable market conditions. Strategic Positioning: Tips on positioning your company to maximize future options, including building relationships with potential acquirers and advisors. The Evolving Role of Legal Counsel: Discussing how lawyers are now integral business advisors, not just legal advisors. Working Directly with CEOs: Joe’s advice to lawyers on effectively collaborating with CEOs versus in-house counsel. Building the Right Team: The value of surrounding yourself with advisors and talent who deeply understand your business and industry. Human Connections in Business: The significance of authentic relationships and trust in driving business success. If you enjoyed our conversation with Joe Hyrkin, be sure to subscribe to Pearls On, Gloves Off for more candid discussions with leaders shaping the legal and corporate landscape. We’d love to hear your thoughts—connect with us on social media and join the conversation! Follow Mary on LinkedIn Rate and review on Apple Podcasts

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.   Follow Mary on LinkedIn Rate and review on Apple Podcasts

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 Rate and review on Apple Podcasts

Welcome to another episode of “Pearls On, Gloves Off,” where we dive deep into the challenges and innovative strategies within the legal and corporate world. In this episode, we flip the tables. Mary O'Carroll, the powerhouse host you've come to know, becomes the guest as Ironclad's Chief Marketing Officer, Leslie Henthorne, steps in to host. This episode is filled with heartfelt reflections, career insights, and a look at what’s on the horizon for Mary. Mary and Leslie dig into: Mary’s Career Journey: From her start in finance, navigating the world of legal operations, and her pivotal role at Google, to betting her career on Ironclad. The Ironclad Experience: Why Mary chose to join a fast-paced legal tech startup, what it was like to build something transformative, and the bittersweet feelings of moving on. Community and Connection: The importance of building a strong, authentic community in the legal space, and why it's more than just a buzzword. Personal Reflections: The challenges and rewards of being a working mom, the quest for balance, and the mentors who shaped her journey. What’s Next: Hints at Mary’s next big move and the future of the podcast. 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: 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: Pearls On, Gloves Off - Apple Podcasts

Welcome to another episode of “Pearls On, Gloves Off,” where we dive deep into the challenges and innovative strategies within the legal and corporate world. Today, Mary is joined by Mick Cox, the VP of Legal Operations at Procore Technologies. They dive deep into the evolution of legal operations and the dynamic journey of growing a legal team from scratch. They explore the challenges and triumphs faced while going through career transitions and the strategies for thriving in high-growth environments. In this Episode: Career Transitions: Mick shares their journey from Salesforce to UC and then Procore, highlighting the unique experiences and lessons learned in each role. Procore’s Evolution: Discover how Procore, a cloud solution for the construction industry, has scaled and how its legal team has evolved in tandem. Legal Ops Insights: The crucial role of legal operations in fast-growing companies, including strategies for effective team growth and process improvement. Team Building: Tips on building and managing a top-tier legal team, including the importance of adaptability, empathy, and a disdain for the status quo. Cultural Impact: How company culture and leadership influence the effectiveness of legal operations and team morale. Tech and Process: The intersection of legal technology and process improvement, and how to prioritize both for optimal efficiency. 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: 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: Pearls On, Gloves Off - Apple Podcasts

Welcome to another episode of “Pearls On, Gloves Off,” where we dive deep into the challenges and innovative strategies within the legal and corporate world. Today, our guest is Andrew Krug, Head of Legal Operations at Twitch, the video live streaming service known for its focus on video game live streaming and esports competitions. Andrew brings a wealth of experience from diverse industries including technology, healthcare, defense, and gaming, making him a unique leader in legal operations.   In this Episode   • The importance of program management skills in legal operations.   • Shifting from traditional legal functions to a more integrated, data-driven approach.   • The critical role of adaptability and leadership in managing legal operations.   • Insights into the structure and responsibilities of the Twitch legal department.   • The difference between project, program, and product management and why these distinctions matter.   • How Twitch is leveraging program management to handle regulatory compliance and improve legal operations.   • The role of technology and data in modernizing legal operations.   • Andrew's journey into legal operations and the benefits of a non-legal background in this field.   • Effective people management and leadership strategies in legal operations.   • Training and development for legal operations professionals.   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: 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: Pearls On, Gloves Off - Apple Podcasts