SY 26-27 Senior Director of Operations

School in the Square•New York, NY

8d•$160,000 - $180,000

About The Position

The Senior Director of Operations is a key member of the Operations team, reporting to the Chief Operating Officer. This role owns the day-to-day systems that let teachers and principals focus on instruction: school operations across all four campuses, legal and regulatory compliance, afterschool programming, and enrollment. The ideal candidate is highly organized, detail-oriented, comfortable managing multiple workstreams at once, and skilled at building systems and relationships that hold up under a fast-paced, growing school network.

Requirements

Bachelor's degree required; advanced degree preferred
Minimum of five years of professional experience, including at least two years managing operations, compliance, or programmatic functions, ideally in a school or nonprofit setting
Experience with charter school compliance and reporting is a strong plus
Skilled at building organizational processes and systems that hold up as an organization scales
Self-starter who generates ideas and leads implementation with enthusiasm and strong organization; comfortable acting decisively in unfamiliar situations
Outstanding attention to detail and ability to manage multiple, competing priorities across departments
Strong written and verbal communication skills; Spanish language proficiency preferred given S2's bilingual campuses
Effective at building relationships and gaining buy-in from a diverse range of stakeholders — families, staff, vendors, and community partners — and comfortable handling ambiguity
Passionate commitment to the mission of School in the Square and investment in our vision and values
Passionate dedication to improve the minds, characters, and lives of students both in and out of school
A Masters Degree and New York state certification as a Teacher of Students with Disabilities.
At least 3 prior years of experience as a special education teacher
Evidence of deep knowledge of special education compliance and effective practice.
An adept problem-solver with a demonstrated ability to think critically, plan strategically, as well as research and perform detailed data analysis
Skilled in written and oral communication to diverse audiences and facilitating decision-making among multiple parties
Proactive and fast learner who thrives in a fast-paced environment
Ability to provide high-leverage feedback via classroom observations and school walk-throughs
Knowledge of the principles and methods for curriculum and instruction, co-curricular and extracurricular design, and the measurement of training and development
Demonstrate ability to interpret policy, procedures, and data
Demonstrate experience using technology as both a management and instructional tool
A high appreciation for and ability to work in and lead a diverse community
Team-player capable of working both collaboratively and independently with a proven ability to: Engage, enlist, and energize others in ongoing improvement of learning and teaching; self-initiate, determine a course of action, and make necessary proposals for change when necessary

Nice To Haves

Spanish language proficiency preferred given S2's bilingual campuses

Responsibilities

Lead Operational Excellence: Champion operational excellence across S2's four campuses by building systems that allow students, teachers, and leaders to focus on exceptional teaching and learning. Establish operational standards and continuously improve facilities, safety, food service, transportation, and campus operations. Build strong vendor partnerships and hold service providers accountable for quality, responsiveness, and fiscal stewardship. Lead long-term operational planning, including space utilization, capital projects, and infrastructure improvements.
Drive Organizational Compliance and Risk Management: Foster a culture of compliance that ensures S2 consistently meets city, state, federal, and charter requirements. Develop systems that proactively manage compliance risks and strengthen organizational accountability. Oversee regulatory reporting, audits, and documentation with accuracy and timeliness. Partner with the Chief Operating Officer and legal counsel to oversee contracts, insurance, and organizational risk. Strengthen policies, procedures, and internal controls to support organizational growth.
Lead High-Quality Early Childhood Compliance: Ensure S2's Pre-K program meets all health and regulatory requirements while maintaining a safe learning environment. Lead the annual recertification process and build systems that support ongoing compliance.
Shape Exceptional Afterschool and Summer Programming: Lead the strategy and operations for afterschool and summer programs that provide safe, engaging student experiences. Manage external partnerships and ensure high standards for quality and accountability. Use enrollment and family feedback to strengthen programming and expand access. Ensure all programs meet licensing, health, safety, and operational requirements.
Lead Enrollment Strategy and Community Engagement: Lead the network-wide enrollment strategy from recruitment through re-enrollment with excellence and compliance. Develop systems that support enrollment growth while meeting New York State charter requirements. Partner with school leaders and the Family Support team to strengthen community outreach. Analyze enrollment data to inform staffing, budgeting, and long-term planning. Build strong relationships with families and community partners that support enrollment and trust.
Build Systems, Develop Others, and Lead Through Influence: Build strong cross-campus partnerships and align teams around shared operational goals. Design systems that improve efficiency, consistency, and organizational scalability. Coach and develop team members through clear expectations, feedback, and accountability. Serve as a strategic thought partner to the Chief Operating Officer and school leaders. Model S2's Relationships First philosophy through integrity, collaboration, and service.