School in the Square
Join School in the Square in reimagining PreK-12th grade education in Washington Heights and Inwood. A tuition-free public charter school, we were founded in 2016 on our "relationships first" philosophy: that students learn best when they feel safe, known, understood and heard; parents are motivated to partner when they are actively invited to participate in their children’s learning journey; and our professional team is inspired to lean into the work when they are valued, supported, included and invested in positive relationship-building across the community.
At School in the Square, you’ll find a diverse, inclusive and welcoming community–no matter your role. With four campuses serving more than 900 students from early childhood through high school, each of us contributes to shaping the next generation of learners, leaders and engaged citizens.
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.
If this sounds like a fit for you, then browse our openings below and learn more about our culture, benefits and more!
School in the Square proudly values diversity. We are an Equal Employment Opportunity Employer.
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SY 26-27 Associate Director of Talent
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Associate Director of Talent
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 Associate Director of Talent:
Our Central Office at School in the Square exists to support and strengthen our schools: our Early Childhood Center, our Elementary School, our Middle School, and our growing High School (9th through 11th for SY 26-27). The Central Office is responsible for delivering high quality academic, operational, talent, human resources, financial, and community engagement services and resources that enable school leaders and teachers to focus on student learning and success. We are looking for dedicated, mission-aligned Central Office staff who will work closely with school-based staff to provide guidance, resources, and problem solving support that will advance instructional quality, organizational effectiveness, and student outcomes.
School in the Square is seeking an Associate Director of Talent to collaborate with the Talent and Human Resources team to ensure talent and human resource resources and services are provided to the School in the Square staff. The Associate Director of Talent will report to our Chief Operating Officer, and drive key talent and human resources processes and initiatives including but not limited to the hiring process, the teaching certification process and performance management support for schools and the Central Office. This person must maintain a high bar of expectations and have a sense of urgency while appearing calm and approachable in all situations. A high degree of professionalism and confidentiality is critical in this role.
Who You Are:
- Competencies and Attributes:
- Strategic thinker who has a proven track record of resolving complex problems anchored in a high level of integrity and judgment.
- Highly organized, conscientious and execution oriented, including exceptional written and verbal communication skills.
- Comfortable and successful in navigating ambiguity and complexity.
- Collaborative mindset where they use strong emotional intelligence and interpersonal skills to actively partner with peers and stakeholders to share ideas and listen to diverse perspectives to align on and make decisions.
- Deep alignment with organizational values and mission.
- Experience and Background:
- Proven experience in talent acquisition, staff training, performance management, or other related fields in a school setting. NYS charter school experience preferred.
- A graduate of a Bachelor’s Degree in Human Resources, Business, Education or relevant content area preferred. .
- Knowledge of performance management systems and managerial best practices.
- Highly proficient in Microsoft Office and Google Suite.
- Comfortability to take initiative and be resourceful; working both independently and collaboratively.
Key Responsibilities:
- Execute and advance the School in the Square talent acquisition strategy to attract and hire diverse and high-quality talent for instructional and non-instructional roles organization-wide. This includes but is not limited to:
- Leading the full recruitment and hiring cycle for all roles;
- Track and analyze hiring metrics to advance the hiring strategy;
- Train and oversee hiring managers implementing equitable hiring practices and processes; and
- Collaborate with hiring managers to analyze retention trends and forecast staff return commitments, informing strategic staff planning for the upcoming school years.
- Collaborate with the Associate Director of Communications on creating compelling recruitment marketing materials and School in the Square branding strategies.
- Partner with Principals to identify staffing risks and needs, and implement proactive and supportive performance management strategies.
- Oversee and implement the School in the Square Teacher Certification Program.
- This includes but is not limited to ensuring all applicable teachers are enrolled in and compliant with obtaining their NYS teaching certification by providing them with guidance, resources and support.
- Lead the human resources onboarding process for new hires.
- Collaborate with the Associate Director of Human Resources on human resources processes and initiatives, including but not limited to offboarding processes, compensation policies and initiatives, and retention strategies.
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 $90,000 - $120,000, 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.
Ready to apply?
Apply to School in the Square
SY 26-27 Senior Director of Community Engagement
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Senior Director of Community Engagement
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 Senior Director of Community Engagement:
Our Central Office at School in the Square exists to support and strengthen our schools: our Early Childhood Center, our Elementary School, our Middle School, and our growing High School (9th through 11th for SY 26-27). The Central Office is responsible for delivering high quality academic, operational, talent, human resources, financial, and community engagement services and resources that enable school leaders and educators to focus on student learning and success. We are looking for dedicated, mission-aligned Central Office staff who will work closely with school-based staff to provide guidance, resources, and problem solving support that will advance instructional quality, organizational effectiveness, and student outcomes.
School in the Square is seeking a Senior Director of Community Engagement to lead our organization’s student enrollment and retention, and community partnership strategy. This position reports directly to our Executive Director, and serves to set the strategy for a successful student enrollment lifecycle that builds awareness and strengthens trust in the community resulting in excellent student recruitment and re-enrollment. The Senior Director of Community Engagement will be responsible for ensuring family experiences and community partnerships are welcoming, responsive, and mission-driven by translating the School in the Square story into a shared identity that deepens relationships.
Additionally, the Senior Director of Community Engagement translates School in the Square’s mission to a strategy advancing the economic and social vitality of the Washington Heights and Inwood communities. This includes strategically managing external partnerships on behalf of the organization, including community-based organizations, local businesses, and civic and local government partners. The Senior Director of Community Engagement will manage and partner with the Community Engagement team, which includes a communications lead, community engagement managers and parent canvassers. The Senior Director of Community Engagement will be vital in ensuring school-based leaders in providing excellent family experiences and communications, as well as driving student re-enrollment and retention.
Who You Are:
- Competencies and Attributes:
- Strategic thinker who has a proven track record of resolving complex problems anchored in a high level of integrity and judgment.
- Highly organized, conscientious and execution oriented, including exceptional written and verbal communication skills.
- Comfortable and successful in navigating ambiguity and complexity.
- Collaborative mindset where they use strong emotional intelligence and interpersonal skills to actively partner with peers and stakeholders to share ideas and listen to diverse perspectives to align on and make decisions.
- Deep alignment with organizational values and mission.
- Experience and Background:
- At least 7 years of experience in community engagement, family engagement, external affairs, or related roles, preferably in PreK-12 education in charter schools, or non-profit organizations.
- A graduate of a Bachelor’s Degree in public policy, communications, education, social work, or other related focus. A Master’s degree is strongly preferred.
- Demonstrated experience in student enrollment, attendance and family engagement strategies.
- Demonstrated experience in navigating diverse communities and implementing strategies committed to equity and inclusion.
- Strong data literacy and experience leading data-driven improvement cycles.
- Exceptional relationship-building and communication skills.
- Bilingual in English and Spanish strongly preferred.
Key Responsibilities:
- Community engagement visionary who sets and implements a community engagement strategy that advances student enrollment and economic well-being within the community.
- Directly manages and coaches the Community Engagement Team to execute on organizational wide priorities, including but not limited to family and community partnerships, school-based engagement strategies, internal and external communications rooted in brand messaging with cultural responsiveness.
- Implements organizational-wide community engagement team professional development vision.
- Monitors and improves community engagement performance to ensure both full class sections (and waitlists) are provided to all schools and that community partnerships demonstrate School in the Square’s commitment and presence to the Washington Heights and Inwood community.
- Collaborate with Central Office leadership and school-based leadership to build and foster relationships with student families and community partnerships to drive community engagement initiatives.
- Lead and facilitates external community engagement initiatives, including ensuring community engagement compliance with all relevant regulatory and legal requirements, and serving as the primary community engagement liaison with the NYS charter authorizers to support renewals, site visits and operational reporting are in compliance.
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 $160,000 - $180,000, 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.
Ready to apply?
Apply to School in the Square
SY 26-27 Chief Academic Officer
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Chief Academic Officer
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 Chief Academic Officer:
Our Central Office at School in the Square exists to support and strengthen our schools: our Early Childhood Center, our Elementary School, our Middle School, and our growing High School (9th through 11th for SY 26-27). The Central Office is responsible for delivering high quality academic, operational, talent, human resources, financial, and community engagement services and resources that enable school leaders and teachers to focus on student learning and success. We are looking for dedicated, mission-aligned Central Office staff who will work closely with school-based staff to provide guidance, resources, and problem solving support that will advance instructional quality, organizational effectiveness, and student outcomes.
School in the Square is seeking a Chief Academic Officer (CAO) to lead the design and implementation of the School in the Square instructional vision and quality across all schools in the organization. This position reports to our Executive Director, and serves as the organization’s senior instructional leader who oversees the Central Office Academics team and school-based instructional leaders. The CAO is responsible for spearheading a vision of and strategy for instruction, curriculum, assessment and school advancement that translates into consistently quality learning experiences for students across all campuses. The CAO has the primary authority and accountability for evaluating for the continuous improvement of both academic performance and the teaching and learning across the network, to ensure our students meet their fullest potential.
The CAO will co-lead the organization’s day-to-day work alongside the Chief Operating Officer, ensuring that our academic priorities and operational systems reinforce one another, and supports school leaders in executing with clarity and consistency. The CAO will directly manage our Principals and partner with them to ensure coherence, rigor, and whole-child development across the organization. As we grow into a Pre-K - 12 academic home for the Washington Heights and Inwood communities, coherence across instructional design and the student experience will starve as an anchoring principle for the CAO. Together with the Principals, the CAO will set expectations for high quality teaching and learning, build school-based leader capacity, and drive measurable student outcomes. The CAO will also directly manage the Deputy Chief Academic Officer(s), who leads organization-wide instructional initiatives in close partnership with the academics team and consultants.
Who You Are:
- Competencies and Attributes:
- Strategic thinker who has a proven track record of resolving complex problems anchored in a high level of integrity and judgment.
- Highly organized, conscientious and execution oriented, including exceptional written and verbal communication skills.
- Comfortable and successful in navigating ambiguity and complexity.
- Collaborative mindset where they use strong emotional intelligence and interpersonal skills to actively partner with peers and stakeholders to share ideas and listen to diverse perspectives to align on and make decisions.
- Deep alignment with organizational values and mission.
- Experience and Background:
- At least 10 years of experience in K-12 education, with significant experience in NYS charter schools.
- Master’s Degree in education, education leadership, curriculum and instruction, or other related focus. Doctorate is strongly preferred.
- Proven success as a Principal and network-wide instructional leader.
- Demonstrated experience improving academic outcomes across multiple schools.
- Experience leading and managing senior instructional leaders at the network level of an organization.
- Deep expertise in curriculum, instruction, assessment, and instructional coaching.
- Strong data literacy and experience leading data-driven improvement cycles.
- Exceptional people leadership, coaching, and change-management skills.
- Familiarity with state accountability systems, charter renewal processes, and authorizer expectations.
Key Responsibilities:
- Academic visionary who, in partnership with their Principal Cabinet, sets and implements a clear, compelling PreK-12 academic vision that is data-driven and embodies School in the Square’s mission and values.
- This includes but is not limited to setting, implementing, and continually evaluating the quality of a cohesive organizational wide instructional framework - curriculum, assessment and school culture systems vision - that includes the integration of Spanish language K-12, special education and culturally responsive and inclusive instructional practices.
- Directly manages and coaches each school Principal to execute on organization-wide priorities, including but not limited to academic performance, school culture, teacher development and community engagement.
- Directly manages the Deputy Chief Academics Officers to lead the academics team of staff and consultants on high quality execution of organization-wide instructional initiatives.
- Sets and implements organization-wide teacher professional development.
- This includes but is not limited to coaching expectations and systems that measurably improve instruction over time.
- Monitors and improves academic performance across all schools using advancement strategies that diagnose root causes and improves student performance with differentiation.
- Collaborate with the Chief Operating Officer to ensure the day-to-day organizational-wide and school-based operations teams effectively support academic priorities.
- Lead and facilitate external and board-facing academic initiatives, including Academic Committee and board presentations and serving as the primary academic liaison with the NYS charter authorizers to support compliance, reporting, renewals and site visits.
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 $220,000 - $250,000, 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.
Ready to apply?
Apply to School in the Square