Head Of Learning Development Jobs in Monroe, WA (NOW HIRING)

Why Overlake?

Picture yourself working on 75 acres of nature, just minutes from Downtown Redmond. Our community is united by a shared sense of purpose, a love of learning, and an unwavering belief in the power of people.

We value tradition and forward-thinking in equal measure. We laugh together, learn together, and lead with compassion. As part of Overlake’s Experiential Education team, you’ll help ensure that every employee can thrive—now and for generations to come.

The Details:

Reports To: Assistant Head of School for Inclusive Excellence

Position Type: Interim, 2026–27 School Year; position begins immediately and ends June 30, 2027.

Wage: $100,000 - $110,000 Salaried Exempt. The wage offered will depend on relevant education and/or years of experience.

Work Hours and Location: The Overlake School: Monday - Friday between 7am and 6pm. This position requires evening, overnight, and weekend responsibilities associated with experiential education programs as outlined in the job description.

The Process: Please include a cover letter, this position will remain open until filled.

Benefits:

• $5 employee premium for all medical plans
• 100% employee coverage for dental and vision plans
• 35% medical, dental and vision coverage for dependents
• 20 to 30 days of paid time off based on tenure for full-time 12-month staff
• Paid Holidays when school is fully closed
• 5-10% employer match based on years of service and employee contribution
• On-site health and wellness
• Professional development allowance
• Up to $2,050 meal allowance for breakfast, lunch, and snacks through on-campus dining.
• Employee Assistance Program
• Long term and short term disability as well as life insurance
• Use of School Library
• New Employee Cross-Department Mentorship Program

Position Overview

The Overlake School seeks an experienced, collaborative, and mission-aligned Interim Director of Experiential Education to provide leadership and continuity for our robust Experiential Education program during the 2026–27 school year.

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 Interim Director will help ensure that these established programs continue to operate well while strengthening the systems, relationships, and practices that support them. Working in close partnership with the Assistant Head of School, the Interim Director will serve as the day-to-day leader and primary point of contact for the Experiential Education team, providing coordination, prioritization, problem-solving, and operational leadership.

During this transition year, the Assistant Head of School will retain responsibility for departmental strategy, personnel management, and significant programmatic and organizational decisions. The Interim Director will work within that framework to support faculty, maintain program quality, and ensure that the department's work remains strongly connected to the mission, vision, values, and educational priorities of the School.

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 Interim Director may be considered for the permanent Director position; appointment beyond the interim term is not guaranteed.

Ensure Exceptional Program Delivery and Educational Integration

• Lead the planning and implementation of major Experiential Education programs, including Retreats, Project Week, Outdoor Education, Service Learning, Service Days, field trips, and other experiential learning opportunities.
• Maintain clear project plans, timelines, responsibilities, and communication for major programs and events.
• Coordinate registration, scheduling, transportation, staffing, communications, vendors, community partners, and other logistics associated with experiential programming.
• Partner closely with faculty and staff to ensure they have the information, resources, preparation, and support needed to lead meaningful student experiences.
• Help faculty connect experiential programming to Overlake's broader educational goals, mission, vision, and values.
• Support faculty in helping students reflect upon and transfer the skills, habits, and principles developed through experiential learning into other parts of school life.
• Encourage thoughtful connections between experiential education and students' experiences as learners, athletes, performers, artists, leaders, teammates, and community members.
• Anticipate operational challenges, develop practical solutions, and participate in experiential programs, including overnight, outdoor, service, and travel experiences, as appropriate.

Support Team Stability and Schoolwide Collaboration

• Build trusting, productive relationships with the Experiential Education team and colleagues throughout the School.
• Create clarity around responsibilities, deadlines, and expectations while encouraging collaboration and shared problem-solving.
• Model calm, professional, responsive, and respectful communication, particularly when navigating competing priorities or challenging circumstances.
• Recognize and draw upon the expertise, institutional knowledge, and contributions of existing team members.
• Foster a department culture oriented toward service to the School, strong partnership with faculty, shared responsibility, and excellent program delivery.
• Work collaboratively across academic, student-life, athletic, arts, operational, and administrative teams, recognizing that experiential education contributes to the whole of a student's Overlake experience.

Learn, Assess, and Strengthen the Program

• Develop a strong understanding of Overlake's Experiential Education philosophy, programs, practices, partnerships, and institutional history.
• Understand how Experiential Education advances the School's mission, vision, values, and broader educational program.
• Listen to faculty, staff, students, and program partners to understand what is working well and where opportunities exist.
• Preserve and build upon successful practices while helping the department respond thoughtfully to evolving school and program needs.
• Strengthen continuity and sustainability by documenting key processes and institutional knowledge.
• Identify practical improvements to systems, communication, faculty support, and program delivery that strengthen an already robust program.
• Help deepen the connection between experiential experiences themselves and the reflection, meaning-making, and transfer of learning that follow them.

• Bachelor's degree required.
• Experience leading or coordinating experiential education, outdoor education, service learning, student programming, educational travel, or similarly complex educational programs.
• A demonstrated understanding of experiential learning as an educational practice, including the importance of reflection, meaning-making, and transfer of learning.
• Experience partnering effectively with faculty and helping educators translate program goals into meaningful student learning.
• 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, listen well, and create clarity within a team.
• The ability to connect departmental work to the broader mission, values, and educational priorities of a school or organization.
• Sound judgment and the ability to remain calm, flexible, and solutions-oriented when circumstances change.
• Respect for institutional history and existing expertise, paired with the ability to identify and implement thoughtful improvements.
• Experience with databases, spreadsheets, project-management systems, scheduling tools, and other technology used to coordinate complex programs.
• Ability and willingness to participate in overnight, outdoor, travel, and weekend programming as required.

Physical Requirements:

• Ability to lift up to 50 lbs.
• Ability to sit/stand/walk for extended periods.
• Must be able to work in school and outdoor environment.

The Opportunity

This role will be particularly well suited to a leader who believes that experiential education is most powerful when students are helped to understand what they have learned and carry that learning into the rest of their lives. The Interim Director will join an established program with significant strengths and will have the opportunity to support faculty, provide steady departmental leadership, and help ensure that experiences beyond the classroom remain deeply connected to Overlake's mission and to the broader education of each student.

Compensation details: 100000-110000 Yearly Salary

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