Lead Instructor (Program Lead Track)

Hiring Process & Timeline

We value a transparent and timely hiring process. Here’s what candidates can expect:

Interview Process:

• First interview: 1:1 with the Program Director
• Second interview: 1:1 with the Executive Director
• Final interview: Panel interview with the hiring committee

Timeline:

• Applications reviewed on a rolling basis; initial interviews scheduled as strong candidates are identified
• Final interviews: Week of June 22–26
• Hiring decision communicated: By July 3
• Position start date: July 13

Format:

• Initial interviews may be conducted virtually
• Final interviews are ideally held in person, with a virtual option available if needed

What You’ll Do

Year 1 Focus: Lead Facilitation + Supported Coordination

• Serve as lead facilitator for a 14-week, after-school youth leadership course
• Guide adolescents through experiential, outdoor, and reflective learning
• Lead group development, manage dynamics, and support individual growth
• Supervise and mentor facilitators and/or program assistants
• Partner with the Founder/Director to learn program operations and logistics

You will not be expected to manage all logistics independently at first—you will be trained and supported.

Long-Term Role: Full Program Leadership

• Oversee all aspects of program implementation and operations
• Coordinate scheduling, transportation, equipment, and daily flow
• Lead staff development, coaching, and performance management
• Maintain program documentation, student progress tracking, and evaluation
• Support recruitment, retention, and program growth
• Lead multi-day trips, hiking, and outdoor experiences

Qualifications & Skills

Required:

• Proven experience facilitating groups of adolescents in outdoor or experiential settings
• Strong group management and de-escalation skills
• Ability to lead reflective discussions and developmental conversations
• Experience working in dynamic, physically and emotionally demanding environments
• Demonstrated leadership and ability to mentor other staff

Preferred:

• Experience with organizations such as expeditionary or wilderness-based programs
• Background in environmental education or wilderness therapy
• Experience supervising or training staff
  Familiarity with case management or student progress tracking

Certifications:

• Current or willingness to obtain: First Aid/CPR/AED
• Current or willingness to obtain: Wilderness First Aid (WFA) or Wilderness First Responder (WFR) strongly preferred

Work Rhythm & Expectations

This role follows a seasonal, school-based schedule:

• High-intensity weeks during active program sessions (afterschool + trips)
• Lighter periods and breaks aligned with school holidays and between program cycles

This is a role for someone who thrives in bursts of meaningful, demanding work balanced by recovery time.

How to Apply

Please submit a resume and cover letter describing:

• Your experience in outdoor experiential education
• Your approach to facilitating youth and managing group dynamics
• Your interest in stepping into program leadership

Apply to programs@cypressadventures.org

Cypress Adventures is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all staff and participants. Learn more at our website