Outdoor Adventure: Lead Instructor (Seasonal Contract)

Season: March 18, 2026 through June 17, 2026

Daily Compensation: $188.50

If you have experience or a strong desire to facilitate youth programs, a commitment to diversity and inclusion, and enjoy collaborative work, join us to create unforgettable experiences for young individuals at stunning outdoor locations and vibrant city settings. 

ABOUT NYC OUTWARD BOUND SCHOOLS

Founded in 1987, NYC Outward Bound Schools is a nonprofit organization that partners with more than 100 public schools across NYC to engage students in equitable, immersive and joyful learning that prepares them to thrive in community, college and career. Our unique approach to programming focuses on adventurous learning — daring exploration, real-world engagement, and meaningful challenge — whether in school, local communities, or the outdoors. In schools, we coach teachers and school leaders to implement Crew, our signature advisory structure that supports student connection and belonging, and Instruction for Deeper Learning in the classroom. Outdoors, whether in the city or upstate at our wilderness basecamp, we deliver adventure programming to students, helping them realize that they can do hard things, and develop leadership skills like collaboration and initiative that transfer to the academic classroom. In all spaces where we work, we support students to be co-creators of their own learning and growth, in environments where their voices are heard and valued. Every day, we are proving that transformation and innovation can happen within a public school system, and that with truly equitable schools, all students — regardless of background or circumstance — are capable of achieving at high levels.

Role Summary :

The Outdoor Adventures: Lead Instructor position at NYC Outward Bound Schools leads students on outdoor adventure courses including hiking, low ropes courses, belaying support on rock climbing walls, and team-building programs at a remote location in Fishkill, NY and various locations across the five boroughs in NYC. During overnight and single day programs, Lead Instructors plan components of outdoor adventure courses for small groups of youth, facilitate adventurous learning experiences, adapt activities based on students’ needs, and ensure a safe and exciting learning environment for all participating youth. The Lead Instructor is also responsible for modeling high-quality instruction and providing professional development, coaching, and support to fellow instructors in order to enhance and differentiate instructional strategies and student engagement. This position requires both remote, overnight work on outdoor courses in NY State and urban adventures in NYC as well as work in the NYC Outward Bound Schools’ headquarters office in Long Island City (Queens). Transportation from our headquarters in Long Island City (Queens) to the Fishkill, NY site is provided, and limited staff housing is available at the Fishkill, NY location for those who need it.This role is expected to work five days a week for the season that runs from March 18, 2026 to June 17, 2026 ( dates subject to change but will be confirmed in seasonal contract) .

Essential Functions: 

Plan for and Provide High-Quality Direct Instruction and Support to Students on Course

• Participate in course planning, including developing educational and outdoor skill lessons, logistics, and scaffolded activity progressions that build toward clear learning outcomes.
• Serve as a Lead Instructor on course, providing guidance, mentorship, and on-site support to Instructors while modeling best practices in facilitation, safety, and youth engagement.
• Instruct experiential education and overnight programs for NYC students while creating a safe, inclusive, and engaging learning environment at outdoor sites and in NYC parks and schools.
• Proactively assess risk and adjust programming to ensure participant safety.
• Oversee medical screening and medication management on course in accordance with organizational protocols.
• Attend and actively participate in all required trainings, including seasonal onboarding, safety certifications, and role-specific professional development.
• Manage and submit required program documentation, including daily course reports, youth surveys, incident documentation, and post-course debriefs, and participate in reflective course debriefs.
• Provide support with course admissions and logistical coordination as needed.

Providing Students with Experiences in a Positive and Inclusive Culture 

• Support students through their outdoor experience by aiding in preparation, ensuring timely meals, supervising sleeping arrangements, and addressing overall needs during overnight programs.
• Instruct students on rock climbing programs in adherence to safety standards and NYC Outward Bound Schools programmatic goals
• Provide clear, effective, and timely communication to students and staff 
• Provide solo instruction to a group of students, when necessary
• Effectively resolve conflict with students, when necessary 
• Ensuring the physical and emotional safety of all students, including those with diverse learning needs.
• Support student health and safety in accordance with NYC Outward Bound Schools policies, including reviewing pre-course medical and behavioral information, supporting admissions needs, and providing appropriate on-course care.

Serve as Model Instructor and Mentor

• Model effective instructional strategies that engage students and promote student engagement and learning outcomes in various modalities.
• Plan, design, and facilitate professional development workshops and training sessions to enhance instructional practices and subject-specific knowledge.
• Step into Site Lead & Lead Instructor role, when required.

Other duties, as required, may be requested.

Qualifications:

Previous experience in outdoor adventure courses and/or climbing is not necessary – what is most important is a strong desire to work with the young people of NYC and expand their view of the world. Minimum qualifications for the role include:

• Must be 18 years or older.
• Commitment to educational equity for BIPOC youth and supporting explicit anti-racist work within our organization and partner schools.
• Able to carry, lift, and move a minimum of 50 pounds for up to five miles per day on uneven terrain (backpacking, hiking, moving gear, supporting evacuations in wilderness settings).
• Able to work outdoors in various weather and temperature conditions.
• Capable of physically delivering proficient belaying assistance to climbers by ensuring both physical and emotional safety on a rock climbing wall
• Able to manage multiple priorities in real-time while managing and resolving individual and group behavioral needs with various tools.
• Experience facilitating youth programming in various settings such as overnight multi-day programs with 24 hour supervision of students, preferred.
• Able to take initiative, carry out tasks individually, and work cooperatively as a team. Able to work with staff that have different styles and experiences.
• Able to support the physical and emotional needs of students who have never camped before.
• Ability to obtain and maintain required outdoor adventure certifications upon hire and through ongoing training, including Wilderness Advanced First Aid, CPR, Epi administration, and Mandated Reporter training.
• Able to obtain clearance through a NYC Department of Education Background Check.

Benefits:

• Comprehensive training and onboarding, including instruction in experiential facilitation, course structure, youth development, safety protocols, and best practices to prepare instructors to work effectively with students.
• Access to Outward Bound’s Employee Resource Groups, and additional employment opportunities within the network
• Three (3) sick days
• This seasonal contract position is not eligible for medical benefits, personal time off (outside of the holidays provided within the season), or other fringe benefits provided to full-time employees.

NYC Outward Bound Schools is an equal-opportunity employer. We prohibit discrimination against and harassment of any employee or applicant for employment because of race, color, religion, sex, gender, pregnancy, genetic information, ethnic or national origin, sexual orientation, marital status, familial status, military or veteran status, qualified individuals with a disability on the basis of the disability, or any other category which may be protected under applicable state or federal law.

Studies have shown that certain populations, including women and people of color, are less likely to apply for jobs unless they believe they can perform every job description task. We are most interested in finding the best candidate for the job, and that candidate may come from a less traditional background. We may consider an equivalent combination of knowledge, skills, education, and experience to meet minimum qualifications. If you are interested in applying, we encourage you to think broadly about your background and skill set for the role.

NYC Outward Bound Schools is an equal opportunity employer. We prohibit discrimination against, and harassment of, any employee or applicant for employment because of race, color, religion, sex, gender, pregnancy, genetic information, ethnic or national origin, sexual orientation, marital status, familial status, military or veteran status, qualified individuals with a disability on the basis of the disability, or any other category which may be protected under applicable state or federal law.