Where Purpose Meets the Path Forward


The Trailhead Leadership Institute is designed to equip leaders at every stage of their journey with the clarity, courage, and practical tools to navigate complexity and lead with purpose—starting from the ground up.

We guide leaders from their own trailheads through immersive, high-impact learning experiences grounded in personal growth, real-world application, and values-based leadership. Their paths may vary, but their successful navigation remains the goal.

We believe every great leadership journey begins with a clear trailhead: a moment of choice, direction, and preparation for the path ahead. We want leaders to find their path, and walk it well.

Robin Rand

General (ret), USAF

Chancellor, Trailhead Leadership Institute

Commander, Air Force Global Strike Command

(2015-2018)

Commander, Air Education and Training Command

(2013-2015)

“After 50 years in leadership and education, I can honestly say I’ve never seen anything quite like what we build at Trailhead. It's just an exquisite mix of a dedicated faculty and staff, a rock-solid, research-backed approach, and truly smart educational technology that brings it all together to make learning more impactful and affordable. I’m genuinely humbled to be part of an organization that truly cares about developing better leaders and the people they lead the way it should be done…with heart, with purpose, and with people in mind.”

1650+ Course Graduates

45+ Completed Cohorts

4.9/5 - Graduate Rating

Course Value, Recommendation to Peers, Instructor Quality, Discussion Effectiveness