Princess Castleberry is the CEO of Castleberry Global and a global speaker disrupting the leadership capacity crisis. She delivers keynotes, workshops, and transformative experiences for leaders who want to make better decisions, stress less, and perform well under pressure.

She’s the voice behind The Truth Is in the Trigger™, the bold new playbook series helping leaders decode what’s really driving their stress, burnout, and stalled decisions.

With 20+ years in enterprise risk management, crisis response, and wellness, Princess brings unmatched insight into what breaks leaders—and what builds them. She’s led high-stakes strategy across global firms in insurance, construction, staffing, and tech, and now partners with executive teams ready to lead with resilience, clarity, and results.

What sets her apart? Her frameworks don’t just inspire—they work. Grounded in global business, behavioral science, and wellness strategy, her programs deliver more than motivation. They provide tools, language, and systems that leaders and teams can apply immediately to make sharper decisions with less stress, eliminate conflict waste, and unlock the behaviors that drive sustainable performance.

Here’s how Princess partners with corporations, associations, and leading nonprofits:

→ Keynotes & Signature Talks: Inspiring urgency, focus, and self-leadership in decision making and resilience
→ Leadership ThinkTanks & Workshops: Deep, hands-on sessions with leadership teams to build capacity and alignment
→ Capacity Redesign & Advisory: Partnerships to restructure people, roles, and workflows—so organizations can navigate pressure, scale leadership, and build sustainable leverage

Her Most Requested Keynotes:

🎤 The Truth Is in the Trigger™: Disrupt the Leadership Capacity Crisis
🎤 Eliminate Conflict Waste™: How to Have Conflict and Still Win Together
🎤 Burnout-Proof™: Building Resilience for the Long Game
🎤 From Gut Feelings to AI Insights

If your organization is growing fast—and you want to expand your leaders’ bandwidth—Princess is the partner you call when performance, well-being, and results all matter.

Foundations of Expertise

Before founding Castleberry Global in 2019, Princess spent over two decades leading enterprise risk and organizational resilience strategies across the U.S., EMEA, and APAC regions. She worked with global firms Marsh, PulteGroup, and Kelly Services, delivering expertise in insurance program management, business continuity, cybersecurity, contract management, HR, legislative compliance, and wellness counseling.

Princess holds:

• A Bachelor’s in International Business from Illinois Wesleyan University (with study abroad at Universidad Complutense in Madrid, Spain)

• A Master’s in Training and Organizational Development from Oakland University

• A Certificate in Wellness Counseling from Cornell University

She’s also a proud alumna of Goldman Sachs 10,000 Small Businesses, Goldman Sachs One Million Black Women: Black in Business, Chase for Business, and Comcast R.I.S.E. programs. Today, she partners with corporate clients, professional associations, and leading nonprofits to drive capacity-centered transformation at scale.

A Voice That Challenges and Connects

Princess commands the stage with strategic clarity, grounded humor, and bold energy. She’s a TEDx speaker and published thought leader featured in Fast Company, Silicon Republic, and Supply & Demand Chain Executive.

Born, raised, and based in Detroit, Michigan, Princess is a wife, mother, and global citizen who immerses her family in cultures around the world—living what she teaches: leadership capacity isn’t just built. It’s something to be protected.