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.

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