Jessica Swank

Chief People Officer at Box leading people strategy for an AI-first content management platform, focused on org design, AI readiness, and building people-led AI initiatives such as internal agents and AI certification.

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Nov 21, 2025 • 58min

269 - Hybrid Teams = People + Agents: Jessica Swank (Chief People Officer, Box)

Jessica Swank, Chief People Officer at Box, shares insights on integrating AI into organizational strategies. She discusses building an 'org brain' and the necessity for managers to lead hybrid teams of humans and agents. Jessica outlines Box's three pillars for AI: Optimize, Elevate, Amplify, emphasizing the importance of rethinking job roles and skills for an AI-driven future. She also addresses managing agent performance, avoiding tech debt, and encouraging HR leaders to experiment with AI personally to stay ahead in the evolving landscape.

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