SY 26-27 Senior Director of Operations

Join our “Relationships-First” 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 Us

• 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 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

About the Role

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.

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.

Qualifications

• 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

Benefits

• Competitive salary and comprehensive benefits
• 401(k) program with a 6% organizational match
• 93% coverage of healthcare
• Longevity bonus
• Generous paid time off
• Access to a federal student loan debt reduction program
• Friendly work environment

Pay

The salary range for this role is $130,000 - $180,000.