Now Hiring

Position:  Lead Instructor
Location: Hartsville, South Carolina
Schedule: Full-time, seasonal rhythm aligned with school calendar, some weekends for trips and events

Compensation: ~$40,000–$50,000 depending on experience

THE OPPORTUNITY

We are seeking an experienced Lead Instructor to step into a key leadership role within our Youth Leadership Program.

This position is designed as a transition into full program leadership. The Lead Instructor will begin by focusing on facilitation and team leadership, while receiving support and mentorship in program coordination and operations. Over time, this role will grow into full ownership of both program delivery and logistics.

This is an ideal role for someone with a strong background in outdoor experiential education who is ready to take the next step into program leadership.

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

TRAINING & ONBOARDING

• 3-week intensive training prior to program launch

• Ongoing mentorship during first program cycle

• Gradual transition of responsibilities over the first year

We are looking for candidates who:

• Are passionate about youth development and experiential learning

• Can guide and inspire adolescents through reflective, hands-on learning

• Demonstrate strong interpersonal, communication, and teamwork skills

• Are open to feedback and continuous growth

• Have the ability to manage group dynamics and adapt to the needs of diverse learners

• Hold or are willing to obtain First Aid/CPR/AED certification (required at Level 2+)

WHO THIS ROLE IS FOR

We are only considering candidates with prior experience in outdoor experiential education.

Strong candidates may have backgrounds in:

• Outdoor education organizations (e.g., expedition-based programs)

• Wilderness therapy programs

• Environmental or adventure education

• Youth leadership or social-emotional learning programs in outdoor settings

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.

WHY THIS ROLE MATTERS

This role is central to Cypress Adventures’ future. The Lead Instructor will carry forward the quality, culture, and impact of the program while helping build the next phase of the organization.

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.