Director of Experiential Learning & Career Pathways

New Trier High School District; Winnetka (IL); On-site; USD 110,000 - 150,000; Full time

Job summary

New Trier High School District seeks a Director of Experiential Learning and Post-Secondary Readiness to lead district-wide programs that connect classroom learning with real-world opportunities. The role emphasizes equitable access, partnerships with industry and higher education, and alignment with the district’s 2030 strategic plan.

The Director will oversee program development, partnerships, budgeting, and data reporting, while guiding staff and collaborating across departments to expand

Qualifications

• Master’s or advanced degree in a relevant field.
• Illinois Professional Educator License with General Administrative or Principal endorsement.
• Minimum of three years’ experience in school leadership and teaching.
• Proven experience in program development, community engagement, and external partnerships.
• Ability to build collaborative relationships with industry, higher education, and community partners.
• A passion for equity, innovation, and developing career and post-secondary pathways for diverse learners.
• Knowledge of trends and evidence-based practices in career technical education and post-secondary readiness.
• Exemplary interpersonal and effective communication skills.
• Demonstration of collaborative leadership.
• Illinois State Board of Education Work-Based Learning Designation preferred.

Responsibilities

• Serve as the strategic and operational leader of the Center for Experiential Learning, advancing a continuum of experiential learning opportunities, career-connected learning, and postsecondary readiness for all students.
• Develop and implement a multi-year vision and strategic framework for career exploration and experiential learning that supports long-term sustainability, scalability, and alignment with district strategic initiatives and ISBE requirements.
• Provide leadership and support to academic departments in developing experiential learning opportunities, career pathways, and programming initiatives that connect curriculum to postsecondary readiness.
• Advance equitable access to experiential learning, career exploration, and postsecondary pathways through collaboration with academic departments and district programs.
• Provide professional learning, resources, and consultation to faculty and staff regarding experiential learning, career readiness, and industry partnerships.
• Partner with district and departmental leaders to expand dual credit, credentialing, and postsecondary opportunities through college, university, and industry partnerships.
• Develop and manage the logistical, procedural, and operational structures necessary to support experiential learning programs, community partnerships, student placements, and off-campus learning experiences.
• Supervise and evaluate staff involved in experiential learning programs and engagement of community partners.
• Provide administrative leadership for the Community Partnership Council and Experiential Learning Team, coordinating priorities and supporting initiatives.
• Oversee budget and fundraising efforts in collaboration with the New Trier Educational Foundation.
• Oversee data collection and reporting of program outcomes, including work-based learning and internship results.
• Lead development of systems to document experiential learning through the Postsecondary Portfolio.

Skills

Leadership

Partnerships

Equity

Communication

Collaboration

Strategic planning

Education

Master’s or advanced degree

Illinois Licensure (Admin/Principal endorsement)

Job description

New Trier High School District seeks a Director of Experiential Learning and Post-Secondary Readiness to lead district-wide programs that connect classroom learning with real-world opportunities. The role emphasizes equitable access, partnerships with industry and higher education, and alignment with the district’s 2030 strategic plan.

The Director will oversee program development, partnerships, budgeting, and data reporting, while guiding staff and collaborating across departments to expand