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Keynote SpeakerPrincess Castleberry

Global Enterprise Risk and Wellness Strategist, helping leaders protect their people, purpose, and profits

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... Read more

Popular Talks

  • Unstuck, Unbothered, and Uninterrupted
  • The Future of AI is Now: Accelerating Life, Business, and Well-being with AI Tools
  • Burnout-Proof Your Team
  • How to Have Conflict and Still Win Together

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Biography

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.

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 Black in Business programs, she has worked with clients including GM Financial, Stefanini, Biggby Coffee, Seco, and leading professional associations and chambers of commerce.

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. Her upcoming book, Every Leader is a Risk Manager: Six Ways to Live, Work, and Build Leverage, set for publication in 2024, will be an essential guide for leaders integrating well-being into their risk management strategies.

Princess has earned a BA in International Business from Illinois Wesleyan University (including study at Universidad Complutense in Madrid, Spain), a Master’s Degree in Training & Development from Oakland University, and a Certificate in Wellness Counseling from Cornell University.

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 thinking, being, and leading.”

"Princess, you were the best! I would recommend you to any leader needing coaching!" Co-CEO and Co-Founder, Biggby Coffee
"Princess, you were amazing, and the experience was exactly what our team needed. The buzz continued throughout the rest of our meeting, and comments continue to flow today. Thank you so much for the targeted and thoughtful approach you took with our team." Henry Ford Health Macomb
"[Having you speak was] definitely a highlight of my events career! I'm so blessed our paths crossed and looking forward to working together more on future events that create a lasting impact!" Director of Events, Detroit Regional Chamber of Commerce
"Princess is in a box by herself. Her powerful messages, along with her contagious sense of humor, give you something like no other speaker can provide." Meeting Professionals International - Indiana
"I've seen hundreds of speakers at TEDxDetroit. Literally, one of the very best - Princess Castleberry! You lit up the stage there...you had me taking notes and rethinking things." Producer, TEDxDetroit
"I engaged Princess to speak and provide training for my legal team. Her engagement, understanding, and ability to translate difficult concepts into relatable examples is unparalleled. The quality of Princess's work is impeccable." Vice President & General Counsel | Stefanini, Inc. North American and APAC

Popular Talks by Princess Castleberry

  • Unstuck, Unbothered, and Uninterrupted

    A highly motivational and actionable keynote for visionary leaders who must get unstuck and build momentum.

    – Learn strategies to communicate and activate your vision and build influence.

    – Navigate and recover from leadership-induced stress triggers.

    – Pivot your leadership style and delegate more effectively.

  • The Future of AI is Now: Accelerating Life, Business, and Well-being with AI Tools

    A highly insightful look at AI beyond its basic productivity and generative functions into its advisory and risk mitigation capabilities.

    – Explore changing leadership and relationship dynamics with the proliferation of AI.

    – Explore unique AI use cases for well-being management.

    – Discuss strategies for responsible AI integration.

  • Burnout-Proof Your Team
    An insightful, story-filled keynote for leaders in high-stress/high-risk roles whose behaviors and decisions have a significant impact on people, operations, and outcomes. – Identify and actively manage the personal and professional triggers causing stress in your workplace. – Learn practices that effectively improve your decision-making and support inclusion. – Practice...
  • How to Have Conflict and Still Win Together
    A highly actionable keynote for leaders to reframe inevitable conflict to spur innovation and collaboration. – Explore common attitudes and views of conflict. – Reshape personal and organizational narratives to view conflict as necessary for innovation and growth. – Learn effective, practical strategies for active listening, self-regulation, and instigating healthy...