Will Craghead
Leadership teams work with Will when they want to grow through foundational principles, honest dialogue, and a clear understanding of what is really holding them back. As a Pinnacle Guide, he helps leaders gain clarity in decision-making, strengthen alignment across their teams, and build organizations capable of sustainable growth under real-world pressure.
Will brings experience as both an operator and a facilitator. As Director of Business Development for an innovative healthcare organization operating outside traditional insurance models, he helped launch and grow a new office, built strategic B2B partnerships, and supported growth across multiple locations. Over the past five years, he has worked with business operating systems and leadership teams firsthand, gaining experience with EOS implementation and other frameworks before finding Pinnacle to be the strongest experience yet for helping teams grow with clarity, ownership, and alignment through a customized, meet-the-business-where-it-is approach.
Trained in both business and biochemistry, Will began his career in medicine, where he saw how deeply systems, incentives, and leadership decisions shape outcomes for real people. Over time, he became increasingly drawn to upstream work: helping leaders design better systems, sharpen strategy, and build healthier organizations.
For the past three years, Will has also led leadership development expeditions hiking Colorado 14ers through The Climb. These experiences have reinforced his belief that leadership growth happens through challenge, honest reflection, trust, and shared responsibility. Clients describe Will as calm, perceptive, and steady under pressure, with a rare ability to hold both truth and compassion in the same conversation while helping teams translate insight into execution.
“When we are no longer able to change a situation, we are challenged to change ourselves.
- Viktor Frankl
