Director of Experiential Education

The Overlake School•Redmond, WA

21h•Onsite

About The Position

Experiential Education is an important expression of Overlake's mission, vision, and values. Through outdoor education, retreats, service learning, Project Week, field experiences, and other opportunities beyond the classroom, students develop skills, habits, and perspectives that deepen their learning and strengthen their capacity to engage meaningfully in the life of the School. At Overlake, the experience itself is only part of the learning. Equally important is helping students make meaning from those experiences and transfer what they learn into other contexts — as students, teammates, performers, artists, leaders, community members, and people. The Experiential Education program therefore depends upon strong partnership with faculty and staff, who help students reflect upon, connect, and apply their learning across the broader Overlake experience. The successful candidate will bring curiosity, humility, sound judgment, excellent organizational and interpersonal skills, and a strong orientation toward partnership and service to the School. They will appreciate the strengths of an established program, learn its culture and history before making changes, and help faculty and colleagues translate experiential learning into meaningful connections across students' academic, co-curricular, athletic, artistic, and community lives. The Director of Experiential Education will provide strategic leadership, operational coordination, and project management for the design and execution of mission-driven, project-based learning experiences for grades 5–12. The position leads the Experiential Education Department and collaborates with faculty, staff, and community partners to ensure the successful delivery of all experiential education programs.

Requirements

Bachelor's degree or equivalent experience required; master's degree preferred.
Minimum of 5 years experience leading or coordinating experiential education, outdoor education, service learning, student programming, educational travel, or similarly complex programs.
Strong organizational and project-management skills, with demonstrated ability to manage multiple stakeholders, timelines, logistics, and competing priorities.
Collaborative leadership and interpersonal skills, including the ability to build credibility, establish appropriate boundaries, and create clarity within a team.
Experience with databases, spreadsheets, project-management systems, scheduling tools, and other technology used to coordinate complex programs.
Ability to lead professional development and curricular initiatives.
Must be highly collaborative, adaptable, and student-centered.
Ability and willingness to participate in overnight, outdoor, travel, and weekend programming as required.
Ability to work in outdoor environments and lead physically active experiences.
Willingness and ability to travel for field-based programs.
Flexibility to work evenings, weekends, and non-standard hours for trips and events.
Capacity to manage logistics, risk, and safety protocols in varied settings.
Must be able to lift and carry equipment and facilitate in dynamic environments.

Nice To Haves

Master's degree preferred.

Responsibilities

Provide clear guidance and direction to the Experiential Education team in planning, executing, and evaluating Service Learning, Outdoor Education, retreats, Field Studies, and Project Week programs.
Set annual departmental goals, establish timelines, and monitor progress through detailed project management systems.
Develop and refine operational systems that support efficient planning, communication, and accountability across programs.
Collaborate with senior administrators, faculty, and staff to align experiential education initiatives with the school’s mission and strategic plan.
Provide clear, proactive, and timely communication to employees, families, and students about programming, such as requisites, itineraries, expectations, safety considerations, etc.
Coordinate and manage all logistics related to Experiential Education programs, including travel logistics, Project Week oversight, process management, risk and safety management, and budget oversight.
Lead and implement a comprehensive communications plan for Experiential Education, including clear and timely updates to students, families, and employees.
Partner with the Communications Office to develop handbooks, websites, FAQs, and promotional materials related to experiential programs.
Provide regular updates and presentations to faculty, staff, and school leadership on upcoming events, logistics, and outcomes.
Serve as a central liaison among departments that intersect with Experiential Education (e.g., Business Office, Operations, Risk Management, Philanthropy, and Academic Divisions).
Refine and oversee curricular scope and sequence, ensuring integration of EE standards with the school-wide curriculum.
Integrate curriculum to EE programs.
Support assessment, reflection, and feedback processes for students participating in experiential programs.
Oversee and participate in overnight student supervision and travel for Retreats, Project Week, Field Studies, and other experiential programs.
Lead or co-lead 10-15 Outdoor or Service Trips per school year (August–June).
Ensure all programs reflect the school’s commitment to diversity, equity, inclusion, and belonging (DEIB).