Princess Castleberry is a leading expert in enterprise risk management with over two decades of experience advising Fortune 500 companies and startups in the insurance, construction, staffing, technology, and healthcare industries.

She has worked with global leaders such as Marsh & McLennan, Pulte Homes, and Kelly Services, building deep and dynamic expertise in global insurance, business continuity, cyber security, and wellness counseling across the U.S., EMEA, and APAC regions.

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As the CEO of Castleberry Global, an experiential learning company at the intersection of risk strategy and well-being, Princess is redefining leadership in today’s wellness-conscious world. A proud alumna of the Goldman Sachs 10,000 Small Businesses and Goldman Sachs One Million Black Women: Black in Business programs, she serves corporate clients, professional associations, and entrepreneurial hubs.

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Princess commands the stage with bold, high-energy, balanced humor and actionable insights. She’s a featured TEDx speaker and thought leader published in Fast Company, Silicon Republic, and Supply & Demand Chain Executive. 

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Her signature talks and programs are anchored in her innovative model, Every Leader is a Risk Manager™, which integrates risk management with well-being to empower leaders to navigate challenges and drive success.

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Born and raised in Detroit, Princess is a passionate global citizen who travels, studies and immerses her family in cultures around the world. She faced adversity early in her career when a leader challenged her belonging and remarked that she didn’t look like a risk manager, to which Princess replied, “Risk management is not a look; it is a way of living, leading, and building leverage.”