Deputy Executive Director Community Schools Strategy

Position Announcement:

The Role

The Deputy Executive Director, Community Schools Strategy serves as a senior leader within the Center for Supportive Schools, reporting to the Executive Director, Community Schools Strategy, and working closely with the Managing Directors of both People & Culture and Budget and Finance Administration. This role ensures the smooth and effective operation of the Community Schools Strategy portfolio by overseeing critical organizational, financial, and programmatic functions. This role will also provide supervision for the leadership and management of a portfolio of NYC Community Schools including managing a team of direct reports.

The Deputy Executive Director provides strategic and operational leadership, manages resources and budgets, cultivates a strong and equitable team culture, and ensures excellence in program execution and partner collaboration. The position is ideal for a mission-driven, systems-oriented leader who thrives at the intersection of strategy, management, and impact.

The Responsibilities

Strategic Operations Leadership

·      Partner with the Executive Director to translate strategic vision into actionable goals, priorities, and operational plans across all functions.

·      Build and maintain productive relationships with NYC schools and district leaders ensuring strong alignment with school/district priorities and partner expectations

·      Drive cross-functional collaboration to strengthen communication across the community schools’ team

·      Represent the Community Schools Strategy team in internal and external leadership meetings and forums, ensuring strategic coherence and clarity of purpose.

·      Lead and manage a portfolio of community schools in NYC.

Finance and Budget Administration, Contracts and Compliance

·      Collaborate with Finance on the design, implementation, and continuous improvement of financial systems and workflows that ensure accuracy, efficiency, and compliance across all Community Schools Strategy operations.

·      Partner with the finance team to strengthen budget tracking, reporting, and forecasting mechanisms that inform strategic decision-making. 

·      Establish and maintain internal controls that promote fiscal transparency, accountability, and compliance to fund priorities and fiscal processes.

·      In coordination with the Director of Contracts and Compliance, Lead the alignment of centralized budgeting practices (invoicing, budget monitoring, accounts payable, etc.) across community schools that comply with NY fiscal requirements, to ensure consistency, transparency, and resource equity.

·      Provide guidance and support to CSDs, Lead CSDs and Senior CSDs to strengthen financial literacy and budget management capacity across the team including serving as an intermediary for BILL processes.

·      Oversee the preparation, management, and monitoring of all program budgets, including budget modifications and amendments, in collaboration with the finance team, Director of Contracts and Compliance, and the Executive Director.

People and Culture

·      Lead hiring processes across the Community Schools team, ensuring consistency, equity, and adherence to organizational hiring practices.

·      Support CSDs in developing clear interview protocols, and selection criteria that reflect both organizational needs and cultural priorities.

·      Collaborate with People and Culture to ensure consistent onboarding experience across the community schools' team that sets new hires up for success and belonging from day one.

-Centralized Employee Relations Support and Partnership

o  Serve as a key liaison between Community Schools leadership team and People and Culture to address employee relations matters confidentially, thoughtfully and fairly.

o  Ensure that staff policies, expectations, and communications are clearly articulated, understood, and aligned with CSS’s values and legal standards

o  Partner with People and Culture and the NYC Program Manager to hold coaching and training sessions for the Community School Team related to HR matters, professional growth and team building

Program Management

-Capturing and Replicating Best Practices

o  Lead the identification, documentation, and dissemination of effective practices, tools, and lessons learned from across CSS’s Community Schools Strategy portfolio.

o  Leverage data, evaluation findings, and staff input to inform program design, resource development, and external communications.

o  Share success stories and best practices internally and externally to strengthen CSS’s visibility, credibility, and influence in the field.

-Continuous Improvement and Professional Development of Community School team members

o  Foster a culture of reflection, learning, and growth across the Community Schools team through intentional coaching, supervision, and structured development opportunities in partnership with the ED and NYC Program Manager

o  Partner with the ED, NYC PM and People and Culture to design and implement professional learning plans that build leadership capacity, technical skills, and cultural competence and ensure that all staff have pathways to learn and advance. 

o  Convene regular learning communities and cross-functional sessions to encourage shared problem-solving and continuous improvement.

Qualifications and Experience

Education: Bachelor’s degree is required. Master’s degree preferred.

This candidate has demonstrated depth of knowledge and experience working within K–12 public school systems, including an understanding of school operations, district structures, and the factors that influence student and staff success. Proven ability to navigate complex educational environments and build effective partnerships with school and district leaders to advance shared goals. They have a minimum of 7–10 years of progressive leadership experience, including at least 3–5 years managing a team of approximately eight or more staff members across multiple functions, programs, or locations. This candidate has a strong financial acumen with demonstrated success overseeing multi-site budgets, managing fiscal planning processes, and ensuring compliance with funder and organizational requirements.

In addition, they have likely had the following experiences and have demonstrated the following attributes:

·      Familiarity with financial and operational systems, including budget management platforms, accounts payable/receivable systems, and organizational accounting software (e.g., QuickBooks, Sage Intacct, or comparable tools).

·      Track record of implementing and refining financial and operational systems to improve efficiency, accountability, and transparency across teams.

·      Excellent communication, collaboration, and people management skills, with the ability to lead, coach, and develop high-performing, mission-driven staff members.

·      Bachelor’s degree in education, public administration, nonprofit management, business administration, or a related field (master’s degree preferred).

·      Familiarity with financial and operational systems, including budget management platforms, accounts payable/receivable systems, and organizational accounting software (e.g., QuickBooks, Sage Intacct, or comparable tools).

·      Track record of implementing and refining financial and operational systems to improve efficiency, accountability, and transparency across teams.

·      Excellent communication, collaboration, and people management skills, with the ability to lead, coach, and develop high-performing, mission-driven staff members.

·      Bachelor’s degree in education, public administration, nonprofit management, business administration, or a related field (master’s degree preferred).

Location

Hybrid-remote position based in NYC, or surrounding area, with in-person expectations across the CSS Community Schools portfolio.

Work Environment/Physical Requirements

·      Prolonged periods of sitting at a desk and working at a computer, including participating in virtual videoconference meetings

·      Communicating with others in writing and verbally to exchange information

·      Ability to lift and move boxes weighing as much as 15 pounds

Compensation and Benefits

The anticipated starting date for this position is Winter 2026. The annual starting salary for this position is $119,200 to $149,000, with a hiring ceiling set at $125,000.

CSS offers the following benefits:

·      Comprehensive and competitive benefits plan, including health, dental, vision, flexible spending accounts, health reimbursement accounts, commuter and transit accounts for employees who meet the eligibility requirements

·      403(b) plan with employer match

·      Generous paid time off

·      Paid holidays and winter break

·      Flexible work option based on job role eligibility

·      Employee Assistance Program

·      Reduced schedule on Fridays during summer months

·      Phone stipend

To Apply

Interested applicants are requested to apply by emailing a cover letter and CV/résumé to resumes@supportiveschools.org. For full consideration, we encourage materials to be submitted no later than Friday, January 9, 2026. Please include (1) the title of the position in the subject line of your email and (2) where you found the position posted in your cover letter. If possible, please email all documents in PDF format. NYC Department of Education fingerprinting and background clearances will be required.

Center for Supportive Schools is an equal opportunity employer committed to inclusive hiring.