Glenbrook High School District 225 seeks a dynamic educational professional to serve as the next Assistant Superintendent of Operations and Student Experiences. The position is scheduled to commence on July 1, 2026.

The Assistant Superintendent of Operations and Student Experiences serves as a senior leader of the District, ensuring that the District’s resources and systems are aligned with its mission and Strategic Plan. The position provides oversight of business services, buildings and grounds, operations, safety and security, and technology services, with a strong emphasis on student-centered decision-making. The successful candidate will possess significant experience in educational leadership and school finance and demonstrate expertise in budgeting, capital planning, and risk management. This leader models integrity, professionalism, and respect while fostering a culture of transparency, collaboration, and continuous improvement.

Applicants should hold the following education/experience qualifications:

Professional Educator License with General Administrative, Chief School Business Official, or Superintendent Endorsement.
Minimum of a Master’s degree in Educational Administration.
Minimum of five years of progressively responsible experience in education, educational administration, or school finance.
Possess knowledge and experience developing and implementing a school district’s annual budget and tax levy, inclusive of debt service and capital project management.
Possess highly developed interpersonal, organizational, and problem-solving skills to make sound and proactive decisions with little or no direction.
Possess excellent communication skills.
Such alternatives to the above qualifications as the Board of Education may find appropriate and acceptable.

Please refer to the attached job description, Board Policy 3:50, and the District's Pay Transparency to learn more about the position. This position comes with a competitive compensation package, family health and dental insurance, full tuition reimbursement, and basic life insurance coverage of up to two times the individual's annual base salary, capped at a maximum of $500,000. The base salary for licensed administrators will be determined by their placement on the teacher salary schedule, with an additional position-specific factor of 1.39, resulting in a salary range of $188,000 to $230,000.

For questions related to the position, please contact Dr. Angelica Romano, Executive Director of Human Resources, at aromano@glenbrook225.org.

Glenbrook High School District 225 holds Niche rankings as the #2 Best School District in America and the #1 Best Places to Teach in Illinois.

We are seeking motivated and energized applicants to join the Glenbrooks!

Glenbrook High School District 225, commonly referred to as The Glenbrooks, offers a public education to approximately 5,100 students in Glenview, Northbrook, and portions of unincorporated Northfield Township. Located 25 miles north of Chicago in a suburban setting, Glenbrook North and Glenbrook South High Schools have a reputation for offering students an excellent, high-quality, well-rounded educational experience. In addition to its two high schools, District 225 also offers alternative learning at Glenbrook Off-Campus and Glenbrook Transition Services. The Glenbrooks foster a student-centered community with engaging, authentic learning experiences that empower individuals to grow, develop their voice, and make meaningful contributions to society. We inspire each learner to apply their abilities, knowledge, and skills, promoting collaboration, adaptability, and a broader understanding of success to positively impact our community and the world.

At D225, you will find more than a job. You will find a career that will inspire you and a community rich in culture and traditions. We invite you to help write our district’s story of excellence by joining our team.

To create a comprehensive high school experience, the Glenbrooks focus on four distinct areas: Academics, Athletics, Activities, and the Arts. Academic success is a top priority for our students, and with nearly 300 diverse course offerings, there are ample opportunities for exploration. In addition to core academic courses in the areas of English, mathematics, science, social studies, and world language, students may pursue special interest classes such as architecture, automotive, debate, graphic design, and music. Glenbrook students enjoy success inside and outside of the classroom through numerous athletic and extracurricular activities programs. The schools offer over 25 different competitive sports and a range of club sports to cater to any athlete. Each school also hosts 70-80 different clubs and activities for students throughout the year.

Staff Benefits include a competitive salary as well as medical, dental, and vision health plans and retirement plans. Additionally, the Glenbrooks offer tuition reimbursement, an excellent mentoring program, extensive professional development opportunities, and partnerships with a university for aspiring administrators.

Apply at www.glenbrook225.org today to join our Glenbrook family!

Discover Glenbrook

Job Openings