Leading Together with Jake Rainey
Week of July 25, 2026
Leading Together is an experiential workshop designed to strengthen the family unit through the lens of leadership. By stepping out of daily routines and engaging in interactive team-building games and initiatives, families explore their unique communication patterns and problem-solving styles in real time.
The session emphasizes identifying core values to create a shared foundation for decision-making and navigating conflict. Through guided reflection and conversation, families work together to co-create a “Family Mission Statement,” helping ensure that daily rhythms align with their deeper purpose.
Participants leave with a renewed sense of their collective resilience and a clear roadmap for facing future challenges as a team.
Jake Rainey is an experiential educator, leadership specialist, and practitioner of human development dedicated to helping individuals and teams reach their sustainable peak. With a Master’s Certificate in Experiential Teaching & Learning and certification as a Life & Engagement Coach, Jake’s work is grounded in the belief that real growth happens when people are safely supported beyond their comfort zones. His commitment to holistic safety is reinforced by dual certifications as both a Wilderness First Responder and a Behavioral First Responder, allowing him to thoughtfully manage both physical and emotional risk in dynamic environments.
Currently serving as Student Life and Leadership Director at Key School and Program Manager for ISEEN, Jake has facilitated high-impact learning experiences around the world. From navigating the Colorado Rockies to leading cultural immersions in Ecuador, his work uses the “ultimate interruption” of adventure to spark deep self-awareness and meaningful growth. A former Colorado State Coach of the Year for Boys Soccer, Jake has a proven ability to transform groups into cohesive, high-performing teams by helping them resolve friction points and align around shared values. In addition to his work at Key School, Jake leads Living At Peak, an organization that designs customized retreats and transformative experiences for teams, groups, and individuals.
Through his Leading Together workshops, Jake brings these leadership principles into the family setting. Using hands-on challenges and reflective dialogue, he guides families in exploring their communication patterns and problem-solving styles. Rather than traditional lectures, Jake emphasizes active engagement, helping families identify their core values, create meaningful mission statements, and build the resilience needed to navigate challenges together.
Grounded in curiosity, wisdom, and practical tools, Jake’s mission is to equip families and leaders with frameworks they can carry forward long after the experience ends.