Chief of Staff

New York, NY: East Harlem /
Network Support Team – Network Leadership /
/ Hybrid
Originally founded in 1991 as Harlem RBI, DREAM has grown to annually serve more than 2,500 youth across East Harlem and the South Bronx through a network of six PreK-12, extended-day, extended-year DREAM Charter Schools and community sports-based youth development programs. Through our commitment to rigorous academics, social-emotional learning, deep family and community engagement, and health and wellness, we create lifelong learners who are equipped to fulfill their vision of success in and out of the classroom. We dream big, as well, with an aggressive five-year plan to expand to serve 3,500 students across seven schools—growing our organization’s impact and leveling the playing field for all children. To learn more, visit

Reporting to the co-CEOs, the Chief of Staff will be responsible for facilitating the execution of complex, organization-wide initiatives and projects in close partnership with leaders across the organization. They will oversee the management of the executive office, ensuring that the co-CEOs’ time is consistently focused on the highest priority areas and planned strategically. This is an exciting opportunity for a highly organized and strategic leader to drive the development of a growing organization through multi-faceted projects in service of its unique mission and model.

Role and Responsibilities:

    • Ensure timely communication and consistent flow of information to and from the co-CEOs office;
    • Monitor key metrics, indicators, and milestones and support the executives’ analysis of overall progress and organizational health;
    • Create systems to ensure the co-CEOs have a diverse set of input and data to make informed decisions;
    • Guide the operational cadence for the senior leadership team, including mapping out leadership team meetings led by co-CEOs and creating and driving the execution of the annual calendar for the leadership team to achieve deliverables;
    • Plan effective internal and external leadership team meetings that drive outcomes aligned with strategic priorities and provide clarity of progress toward goals, and ensure airtight systems for follow-up and follow-through;
    • Facilitate the annual organization-wide planning process and support the leadership team in scoping, planning and execution of strategic initiatives; ensure regular check-ins and report-outs of progress towards goals;
    • Design and lead the project management of organization-wide retreats, conferences, and other special events in collaboration with cross-functional teams;
    • Oversee large, often cross-functional, organization-wide projects or initiatives, including bringing together important stakeholders and helping to drive decisions;
    • Directly manage administrative professionals who are part of the executives’ offices to ensure the co-CEOs’ involvement in projects or decision-making processes takes place at key times, where their input and authority are most needed;
    • Ensure the strategic management of the co-CEOs’ time so it’s aligned with the highest priorities;
    • Support the onboarding and assimilation of direct reports to the co-CEOs by supporting the drafting of 90-day plans and assimilation activities internally and externally;
    • Build meaningful and trusting relationships with staff, scholars and families to facilitate positive scholar outcomes and contribute to a high-performing organizational culture;
    • Support executive communications efforts led by the Communications & Brand team by ensuring they have the necessary information and context at hand;
    • Perform additional duties as assigned.


    • Bachelor’s degree required;
    • Advanced training, experience or degree in business administration or similar fields, preferred;
    • Extensive leadership experience with a track record of successful management and collaboration;
    • Deep knowledge of best practices in organizational development and project management;
    • Excellent communication and collaboration skills;
    • Action-oriented, versatile, and efficient;
    • Proven ability to support and interact with senior management;
    • Excellent verbal, written and interpersonal communication skills, with a solutions-oriented attitude;
    • A strong work ethic, supported by commitment and airtight follow-up and follow-through;
    • Ability to manage multiple projects while working in a fast-paced environment;
    • Organized, proactive and detail-oriented with superior time management and troubleshooting skills;
    • Impeccable integrity, including the ability to maintain a high level of confidentiality and discretion;
    • A strong belief in the mission and values of DREAM, including the belief that all students can succeed, and a deep desire to make a difference in the lives of our students, families, and community.

DREAM requires vaccination against COVID-19 for all employees.  Reasonable Accommodations based on a qualifying disability or sincerely held religious belief are being considered in accordance with applicable law.


At DREAM, diversity, equity, and inclusion are a matter of mission. 

From our schools to our playing fields, DREAM is committed to building a team where each individual can bring their full identity and experience to work because representation matters—it enriches our team culture, enhances our ability to innovate, and strengthens our impact in and out of the classroom. DREAM engages staff that represent and appreciate the diversity of our majority Black and Hispanic student body, while working to ensure that our practices are equitable, welcoming, and productive. We are dedicated to creating a world where youth, especially youth of color, have permission to dream—along with the tools and opportunities to make their dreams reality. 
Come dream with us.


All Kids Can. This Kid Can.
DREAM is Family.
Fun is a Serious Value.
Teamwork Makes the DREAM Work.
Fail. Persist. Exceed.