Bilingual Deputy Administrative Head of Schools

Bilingual Deputy Administrative Head of Schools

Join Our “Relationships-First” Team:                                

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: making sure that we engage, educate, and empower our students, families, and professional team members. We invite you to be a part of a 175+ team whose mission-aligned culture offers sustainable, rewarding career paths in teaching, operations, and leadership, built on relationships-first 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 School In the Square?       

As a “relationships first” community, we... 

• Demonstrate care for colleagues, students and families,
• Commit to learning and growing together,
• Invest in relationship-building work,
• Support each other with competitive benefits including a 6% 401k match, 93% coverage of healthcare premiums, generous full company closures and PTO policies, and more!

Our Bilingual Deputy Administrative Head of Schools

The Bilingual Deputy Administrative Head of Schools is a pivotal member of the leadership team at School in the Square, instrumental in shaping and executing a vision for high-functioning operations that underpin student success. This leader champions administrative excellence, drives systematization, and supports the development of both school-based and network operations and talent teams. The role demands a strong leader who thrives on structure, collaboration, and building sustainable systems within a bilingual, community-driven charter network.​ The Bilingual Deputy Head of Schools partners with the Head of Schools and Deputy Instructional Head of Schools to

• Ensure that their work centers the needs of children and families; 
• Be coordinated in deep partnership with each other and with Principals;
• Focus on making sure that the whole has to be greater than the sum of its parts by bringing their expertise and responsibilities to the collaborative task of ensuring all students succeed.

Key Responsibilities 

Organizational Leadership

• Collaborate with the Head of Schools and Deputy Instructional Head of Schools to set and execute strategic priorities across the network;
• Translate organizational vision into clear operational systems, ensuring alignment across school sites;
• Serve as a key thought partner in long-term planning, growth strategy, and network-wide initiatives.​

Operational Excellence & School Support

• Develop and maintain clear, replicable operational systems and procedures across all campuses (e.g., scheduling, procurement, attendance, inventory);
• Monitor and support school-based operations teams in the execution of daily operations to ensure smooth school functioning;
• Ensure compliance with state and city regulations, including those related to facilities, safety, food service, health, and transportation.​

Systems Design & Process Improvement

• Establish and refine systems for tracking and improving administrative metrics, such as attendance, enrollment, and compliance documentation;
• Lead cross-functional project management efforts to improve efficiency and effectiveness across departments;
• Promote a culture of data-driven decision-making and continuous improvement among admin and ops staff.​

Human Resources & Staff Development

• Oversee all aspects of human resources, including recruitment, onboarding, performance management, compliance, and offboarding;
• Design and implement professional development systems for operations and administrative staff;
• Build leadership capacity among school-based operations managers and administrative teams through coaching, training, and accountability systems.​

Talent Strategy & Hiring

• Design and lead strategic hiring systems across the network, including workforce planning, recruitment, onboarding, and retention initiatives;
• Partner with school leaders to ensure hiring practices reflect School in the Square’s values of diversity, equity, and bilingual community representation.

Budgeting, Procurement, and Resource Management

• Partner with finance and school-based operations teammates to create and manage operational budgets across schools;
• Ensure procurement systems are efficient, cost-effective, and equitable across the network;
• Monitor inventory, asset management, and vendor accountability.​

Facilities, Safety & Compliance

• Ensure quality planning and execution of school safety protocols, drills, and crisis response plans;
• Drive initiatives that promote physical safety, emotional wellness, and a welcoming environment for students and families;
• Supervise the Director of Facilities to ensure buildings are in compliance state and local requirements, as well as oversee contracts with vendors.

Engagement & Collaboration

• Establish quality family engagement standards and strategies responsive to the needs of the community;
• Partner closely with instructional leadership to ensure administrative systems support teaching and learning;
• Act as a liaison between network and school sites to ensure consistent implementation of school operations and high standards;
• Regularly report to the Head of Schools on progress toward goals, challenges, and operational health.​

Qualifications

• Bilingual (Spanish/English) required; strong written and verbal proficiency in both languages.
• Minimum 7 years of experience in school operations or administrative leadership, including 3+ years in leadership or supervisory role. 
• Demonstrated experience developing, implementing, and managing operational systems in a school or educational setting. 
• Proven track record of leading high-performing teams and developing talent through coaching and capacity-building. 
• Experience designing and implementing talent systems including hiring, onboarding, evaluation, and retention strategies. 
• Deep understanding of HR practices, compliance, budgeting, procurement, and project management in a K-12 environment. 
• Excellent problem-solving skills and ability to make decisions grounded in equity, data and organizational values. 
• Strong interpersonal skills and emotional intelligence; able to build relationships and communicate effectively with a wide range of stakeholders including staff, students, families and community partners. 
• Commitment to equity, inclusion, and serving a bilingual, multicultural community. 
• Familiarity with NYCDOE/NYSED charter regulations, facilities management, and school safety protocols. 
• Master's Degree in Education Leadership, Public Administration, Business, or related field required. 

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 ultra competitive salaries. The salary range for for the Bilingual Deputy Administrative Head of Schools at School in the Square is $180,000-$220,000. 

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
• access to a federal student loan debt reduction program
• 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.