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This is a conversational interview (podcast episode) between Mary O’Carroll and Alyssa (Alyssa) Harvey Dawson, HubSpot’s Chief Legal Officer. Alyssa walks through her 20+ year in-house legal career across companies of varying sizes (Autodesk, Netflix, Harman, Sidewalk Labs, Gusto) and describes her role at HubSpot overseeing legal and compliance teams focused on helping customers. Major themes: the legal implications of AI and the need for data stewardship and transparency; the evolving in-house CLO/GC role as a strategic business partner; how outside counsel should provide pragmatic, business-focused advice; developing business judgment and team training; mentorship and career navigation; and how improv taught agility and listening skills. The interview also includes practical examples (global customer considerations, product partnership) and closing career advice about adaptability and prioritization.

Questions this video answers

Over 20 years.

More than 14 countries.

Almost two years.

YouTube video titled "#52 From Improv to AI HubSpot CLO Alyssa Harvey Dawson" (podcast episode).

September 3, 2025.

Chapters

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