SY 26-27 High School College and Career Assistant Principal

School in the Square•New York, NY

1d•$110,000 - $130,000

About The Position

Join Our “Relationships-First” Team: We invite you to be a part of a team whose mission-aligned culture offers sustainable, rewarding career paths in teaching, operations, and leadership, built on collaboration and mutual support. Experience the difference at a workplace that celebrates and cultivates each team member’s passions, skills and multi-disciplinary interests as we build a brighter future together, one student at a time. Our High School at School in the Square opened its doors in Fall 2024 where we began creating opportunities and access for our students that go beyond the core content areas. Our high school community provides students with educators who have great content expertise and passion for their content, while empowering them to have the autonomy and resources to get the job done in the most creative, effective, and fulfilling way possible. We are looking for a dedicated, mission-aligned Assistant Principal to help lead our High School. Reporting to our Principal and in collaboration with a diverse and committed School Leadership Team (SLT), the Assistant Principal of College and Career will spearhead our efforts to ensure high academic standards, aligned to rigorous college and career pathways, while also focusing on the social-emotional needs of all students. This AP will serve as the school’s lead for designing, implementing, and refining a comprehensive college and career readiness strategy grounded in equitable practices. They will establish clear goals, metrics, and systems to drive continuous improvement in college acceptances, scholarship attainment, and career pathway achievement, and collaborate with the Principal and leadership team to align college and career goals with the school’s mission and academic priorities. As a motivating and positive leader, the Assistant Principal will lead, supervise, and evaluate the performance of college and career counselors and other staff within the department; provide coaching, feedback, and professional development to build counselor capacity in advising, data analysis, student engagement, and equity-centered practice; and oversee case management systems that ensure all juniors and seniors complete post-secondary plans, applications, financial aid forms (e.g., FAFSA), and career exploration experiences.

Requirements

Prior college and career leadership experience in a high school setting, especially within urban or charter school environments.
Experience in secondary education leadership or related roles — including program management, counseling oversight, or administrative responsibilities.
Deep understanding of college admissions, financial aid processes, standardized testing, credentialing, and career development frameworks.
Demonstrated success coaching adults (e.g., counselors, advisors) toward improved practice and measurable outcomes.
Strong analytical skills with experience using data to inform strategy, create interventions, and monitor impact.
Excellent communication and relationship-building skills with students, staff, families, and external partners.
Commitment to culturally responsive practices and equitable access to post-secondary opportunities.
A consummate coach and strong relationship builder, you get personal fulfillment by succeeding through others and developing leaders
Familiar with restorative practices, a strong believer in anti-racism education, culturally responsive and sustaining pedagogy, trauma informed practices
A graduate of a Master’s Degree in Education or comparable degree

Nice To Haves

Valid New York State Teaching Certification preferred
Professional fluency in Spanish preferred

Responsibilities

designing, implementing, and refining a comprehensive college and career readiness strategy grounded in equitable practices
establish clear goals, metrics, and systems to drive continuous improvement in college acceptances, scholarship attainment, and career pathway achievement
collaborate with the Principal and leadership team to align college and career goals with the school’s mission and academic priorities
lead, supervise, and evaluate the performance of college and career counselors and other staff within the department
provide coaching, feedback, and professional development to build counselor capacity in advising, data analysis, student engagement, and equity-centered practice
oversee case management systems that ensure all juniors and seniors complete post-secondary plans, applications, financial aid forms (e.g., FAFSA), and career exploration experiences