SY 26-27 High School College and Career Assistant Principal

High School College and Career Assistant Principal

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.

Why Educators Choose S2:

• A “Relationships-First” culture where you’re valued, supported, and included


• Collaborative planning time and mutual support


• Opportunities to lead initiatives that strengthen student growth at every stage of their PreK–12 education


• Competitive salary and comprehensive benefits including offering a competitive compensation package, including a strong benefits program and a 401(k) with a 6% organizational match


• A bilingual, community-rooted model serving Washington Heights and Inwood including a pantry partnership, Bachata Nights, multicultural festivals, and a reading initiative. 

Our High School College and Career Assistant Principal:

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.

Who You Are:

• 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


• Valid New York State Teaching Certification preferred


• Professional fluency in Spanish preferred

What Can You Expect From Us

At S2, we take as much care of our staff as we do of our students. S2 is committed to supporting our staff by helping them build sustainable, rewarding careers that center on each individual’s passions and multi-disciplinary interests. All of our faculty and staff are valued professionals and we are proud to provide team-building and collaboration, comfortable and friendly working conditions and more, to ensure our team members have the tools they need to succeed.

In addition to meaningful and rewarding work, School in the Square provides competitive salaries. Expected salary range for this role is $110,000 - $130,000, depending on experience, level of education, required certifications, internal equity, and the budgeted amount for the role.

Additionally, we provide opportunities for supplemental compensation, an excellent benefits package with:

• a 401K program with a 6% organizational match


• 93% coverage of healthcare coverage


• longevity bonus


• generous paid time off


• and a supportive work environment. 

School in the Square understands specific groups are subject to marginalization. We believe these powerful groups should be centered in our community and are highly encouraged to apply. We are an Equal Employment Opportunity Employer.