• Full Time
  • Cupertino, CA
  • This position has been filled

Website Tessellations_S Tessellations

A K-8 progressive school tailored for gifted students

Director of Outdoor Education

Are you an experienced, imaginative, and collaborative educator who believes in progressive education? Do you enjoy creating meaningful learning experiences, and being part of a diverse, supportive and talented community? If so, please consider joining our team at Tessellations. We are currently accepting applications for a full-time Director of Outdoor Education. Successful applicants start Summer or Fall 2023. Competitive salary and full benefits available.

Tessellations is a progressive K-8 non-profit school for gifted learners based in Cupertino, CA. Our mission is to provide challenging experiential education that recognizes and nurtures the individual strengths of gifted learners, empowering them to confidently express who they are and pursue a meaningful life. At Tessellations, community is a core value, as it is the reason our small and mighty school was able to form and thrive despite the global pandemic. Our team consists of passionate, qualified and dedicated staff from diverse backgrounds and includes nationally renowned gifted experts. Our first year was online only. In our second year, we moved onto our beautiful campus and quadrupled in size, and we also added our Nature Campus. We’re in our third year with excellent staff and student retention, and extremely high family satisfaction. Next year we’ll be moving again to a larger campus in order to house our growing population, and in Fall 2024 we will launch our high school.

The Nature Connections program consists of weekly Outdoor Education classes provided to all students and is primarily designed to take place at our Nature Campus located in the nearby foothills of the Santa Cruz Mountains. Naturalists facilitate a wide range of outdoor experiences to allow students to deepen their connection with and sense of belonging in the natural world. Our blossoming Nature Journey curriculum is connected with students’ on-campus experiences and Homeroom Journeys, and is designed to be a blend of emergent Nature Connection experiences and project-based learning.

If you join our team you will help us grow our program and continue designing and delivering a rich, immersive learning experience. You will be heard, respected, and celebrated for your talents and efforts. You will work with students who love to learn, engaged parents who are grateful for your work, and supportive colleagues that will help bring out your best.

Primary Responsibilities

  • Hold the vision and direction of the Nature Connections program as connected to the school mission and vision. Facilitate group discussions about pedagogy, programmatic goals, and responsibilities. Act as liaison with admin team and families. Ensure programmatic compliance with laws and school policies and procedures
  • Support and supervision of Naturalists (expected team size for 2023-2024: 10 including the Director). Ensure that Naturalists understand their roles and responsibilities. Create opportunities for Naturalists’ success and resolve issues as they arise. Utilize the Tessellations coaching structure to improve teaching performance. Assist Naturalists in setting and meeting professional goals. Observe and offer constructive feedback. Create and/or facilitate professional development opportunities. Coach Naturalists on strategies for differentiation and assessment. Conduct formal evaluations of Naturalists in collaboration with Assistant Head of School and/or Director of Education.
  • Teaching – Lead lessons within the Outdoor Education program as needed within the teaching schedule and program structure. Model instructional strategies in a variety of ways that align with teaching gifted students in an outdoor setting.
  • Curriculum – Assist Curriculum Leads and help Naturalists co-plan lessons as appropriate. Track standards to ensure a comprehensive program. Manage the report card process for the Nature Connections Program.
  • Staffing – Identify staffing needs and support in hiring process. Assist in figuring out substitute needs for the Nature Campus. Act as substitute as needed
  • Camping – Oversee the planning and running of camping trips in conjunction with Naturalists. Facilitate the process for obtaining hiking and camping permits. Attend and/or lead camping trips as needed.
  • Operations, Safety, Systems, and Logistics – Develop, oversee, and enforce safety protocols and logistical systems, including emergency plans and weekly schedules. Act as liaison with Via West, the operators of our Nature Campus


  • Education or work experience equivalent to graduation from a four-year college or university
  • Strong background in environmental education programming and curriculum development and implementation, or equivalent
  • Prior experience teaching students in Elementary and Middle School
  • Prior studies, familiarity with, and experience learning and teaching natural history and science
  • Demonstrate responsibility, organization, flexibility, strong executive functioning, and sound judgment as it relates to the delivery of youth program activities in a team setting
  • Excellent leadership and communication skills responding calmly to challenges
  • Experience planning and leading overnight outdoor trips with students
  • Familiarity with and commitment to DEIJ work and restorative justice practices
  • Passing a criminal background check upon hire
  • Able to drive a 12-passenger vehicle to transport students
  • Proficiency with technology (Google Suite in particular)

Bonus Points (not required)

  • Experience with gifted students
  • Class B drivers license or willingness to obtain one upon hire
  • Wilderness First Responder Certification


Salary range: $85,000 – $115,000

Benefits include medical, dental, vision, life, 401(k), flexible spending account, paid time off, holidays, and school breaks.

To Apply

Please submit a cover letter and resume to careers@tessellations.school. For more information about our school, visit https://tessellations.school.

Tessellations is an Equal Opportunity Employer — we do not discriminate against any employee or job applicant on the bases of race, color, gender, national origin, age, religion, creed, disability, sex, or reproductive health decision making.

Tagged as: K-6, Middle School