Director of Experiential Education

Description

Reports To: Assistant Head of School
FLSA Status & Schedule: Full-time, salaried, exempt; instructional support following the school year schedule plus twenty days. Evening, overnight, and weekend responsibilities associated with experiential education programs as needed.

The Process: Please submit your resume and cover letter to be considered for the position. This position will remain open until filled. We are flexible on start date - it could be as early as the right candidate is available, or as late as August 2027 for the 2027-2028 school year.

Position Overview

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.

What You Will Do

Leadership, Oversight, and Strategic Direction

• 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.

Program Management and Coordination

• Coordinate and manage all logistics related to Experiential Education programs, including:
  • Travel logistics: Arranging flights, ground transportation, accommodations, and trip itineraries for students and staff.
  • Project Week Oversight: Support and lead Project Week logistics, planning, and programming. From working with staff and faculty to overseeing the student and family experiences in the program. 
  • Process management: Streamlining and managing the application, permission forms, and data systems related to student participation.
  • Risk and safety management: Ensuring all trips and events follow school safety protocols, supervision ratios, and emergency response plans.
  • Budget oversight: Managing program budgets, vendor contracts, and purchasing processes to ensure fiscal responsibility.

Communication and Stakeholder Engagement

• 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).

Curriculum and Student Learning

• 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.

Program Delivery and Supervision

• 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).

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.

Physical and Other Requirements

• 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.

This role will be particularly well suited to a leader who enjoys making complex programs work well, helping teams stay coordinated, and creating the conditions for students and colleagues to have exceptional experiences.