Booking Holdings’ CHRO on Leading 24,000 Employees at the Crossroads of Culture and AI

CHROs today face a pressing mandate: how to build cultures of clarity and belonging while navigating hybrid work, rising employee expectations, and the disruptive pace of AI. The risk of drifting into transactional cultures is real, yet so is the opportunity to shape organizations where culture drives performance and technology enables growth. The question for CHROs is, how do you create alignment while preparing your workforce for what’s next? In this episode, Paulo Pisano, EVP and CHRO at Booking Holdings—and the leader shaping the Future of Work for 24,000 employees—shares how culture and AI intersect to redefine leadership. He explains why culture is ultimately about how people get things done, why clarity is the cornerstone of inclusion, and what it means to bring your “whole professional self” to work. Paulo also addresses polarizing topics at work, the trade-offs of remote versus office culture, and how employee sentiment, trust in leadership, and decision effectiveness can be measured as cultural indicators. Finally, he offers a forward-looking view on how generative and agentic AI—through both HR applications and customer-facing tools—are accelerating productivity and experimentation, and what this means for reskilling and the future role of HR in shaping culture.

 

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