Leadership Development Specialist

HIGH 5 is GROWING! Leadership Development Specialist (Brattleboro, Vermont & Keene, New Hampshire)

High 5 Adventure Learning Center is recognized internationally for our leadership in experiential education and adventure learning. Schools, colleges, camps, businesses and organizations across the globe partner with us to unlock the potential of their people. Through our Edge of Leadership (EOL) Program, we help students grow their leadership skills through hands‑on learning experiences, reflection, and human connection. As an educational nonprofit, we believe in experiential learning as a catalyst for positive change—and we’re looking for someone who wants to learn and grow with us.

We seek a full‑time Edge of Leadership Leadership Development Specialist to join our team. This position serves as a lead facilitator and relationship‑builder, delivering transformational learning experiences for both students and adults, while also helping advance the growth and impact of the EOL program.

The ideal candidate is an experienced educator, facilitator, or leadership development professional. We’re looking for people with significant experience working with youth and adults, possessing exceptional facilitation skills, and can confidently partner with educators, principals, district leaders, and community stakeholders. This individual will play an important role in program delivery, curriculum development, and the ongoing evolution of the EOL model.

High 5 is committed to inclusivity. We recognize that growing our team to include people from all backgrounds, identities, and perspectives makes our work more effective as we strive to strengthen the communities in which we work. We encourage all applicants with the requisite qualifications to apply.

• Lead high‑quality experiential learning programs for students in grades 5‑12.
• Facilitate professional learning workshops, educator cohorts, retreats, and leadership development experiences for adults.
• Create engaging learning environments that foster connection, self‑awareness, collaboration, resilience, and leadership.
• Serve as a facilitator for challenge course and outdoor experiential learning experiences.

• Build and maintain strong trusting relationships with educators, administrators, and district leaders.
• Collaborate with partner schools to align programming with identified goals and priorities.
• Represent Edge of Leadership in meetings, presentations, conferences, and community events.

• Contribute to the design, refinement, and implementation of EOL curriculum and professional development offerings.
• Help identify emerging needs and opportunities within partner schools.
• Support program evaluation, reflection, and continuous improvement efforts.

• Contribute to organizational planning and strategic initiatives.
• Contribute to a thriving High 5 culture by engaging in reflection, sharing learning, and modeling leadership that supports collective growth.
• Work collaboratively across departments to strengthen High 5’s overall impact.

Required:

• Bachelor’s degree or equivalent professional experience.
• Five or more years of experience in education, youth development, leadership development, experiential education, coaching, organizational development, or a related field.
• Demonstrated excellence in facilitation with both youth and adult audiences.
• Strong relationship‑building, communication, and presentation skills.
• Ability to work independently while contributing to a collaborative team culture.

Preferred:

• Experience leading professional development for educators.
• Experience working with school systems and educational leaders.
• Background in experiential, adventure‑based, or social‑emotional learning.
• Familiarity with working with Google Suite products.
• Challenge course facilitation experience.

Salary: $55,000 to $65,000, depending on experience and qualifications. We are particularly interested in experienced candidates who bring demonstrated expertise in facilitation and leadership development. Compensation within the range will reflect the depth of experience and other preferred characteristics the candidate brings to the role.

Benefits include:

• 200 hours of Combined Time Off (CTO)
• 16 paid holidays
• Professional development and training opportunities
• Health and life insurance, as well as opportunities for dental, vision, and short-term disability insurance.

Please send your cover letter and resume to hiring with “EOL Senior Leadership Development Facilitator” in the subject line. No phone calls, please.

High 5 Adventure Learning Center is an equal opportunity employer and encourages qualified candidates from all backgrounds to apply.