John Winsor

John Winsor is a globally recognized leader in the future of work and AI-driven workforce strategies. Recently appointed as an Executive Fellow at Harvard Business School’s Digital, Design, and Data Institute, he focuses on the evolving intersection of work, technology, and talent.

Winsor is dedicated to empowering leaders to confidently navigate digital disruption and harness the transformative potential of AI. A serial entrepreneur, six-time author, and global thought leader, he uniquely blends strategic foresight with entrepreneurial agility, guiding organizations through profound technological change with clarity, insight, and measurable impact.

Known for his ability to translate complex innovations into actionable strategies, Winsor’s work emphasizes resilience, curiosity, and human-centric leadership. His approach is deeply informed by his experiences in the world of high-stakes entrepreneurship, where adaptability and innovation determine success. Leveraging this entrepreneurial spirit, he helps senior executives and global teams cultivate dynamic responses to uncertainty, fostering organizational cultures that thrive amidst rapid technological evolution.

Winsor has advised Fortune 500 corporations, technology startups, major consulting firms, and private equity groups, delivering outcomes such as increased organizational agility, sustained innovation pipelines, and enhanced competitive positioning. His books provide leaders with practical frameworks for navigating modern business challenges, from AI integration to open-talent ecosystems.

As an Executive Fellow at Harvard’s Digital, Data, and Design Institute, Winsor designs and delivers workshops that transform leadership capabilities and drive strategic breakthroughs. His distinctive leadership insights are further enriched by his passion for adventure sports, including climbing and surfing, which offer powerful metaphors for overcoming business challenges.