Chief of Staff to the CEO

OUR MISSION:  Our mission is to inspire and empower all young people to take control of their future.  

OUR VISION:  We envision a world where everyone has access to an equitable path to success.  

PROGRAM DESIGN:  RTS facilitates a variety of youth programs including after-school, summer camps, retreats, conferences and summer employment opportunities reaching thousands of young people throughout NYC each year. RTS emphasizes the youth development practice of the Circle of Courage in all our programs; creating an environment of Belonging, where young people can build their Independence, find and develop their Mastery skill, and practice Generosity in their communities. At the core of our programs are staff training strategies that enable our young professionals to develop extraordinarily meaningful relationships with the young people in their care who we call Our Future Leaders because that is what they all are.  

PRIMARY FUNCTION:  Roads To Success (RTS) seeks a strategic, mission-driven Chief of Staff to partner closely with the CEO in advancing organizational effectiveness, cross-functional execution, and strategic growth. The Chief of Staff serves as a senior thought partner and operational leader, ensuring alignment between strategy, leadership, and day-to-day execution across a complex, multi-site youth development organization. 

  ORGANIZATIONAL ROLE:  

Reports To: Supervisor(s): Chief Executive Officer 
Schedule: Fulltime Monday- Friday, Occasional weekends 
Compensation: $90,000-$110,000 

Location: New York, NY (with travel to program sites in Harlem, Brooklyn, and the Bronx as needed) 

  RESPONSIBILITIES:  

• Partner with the CEO to translate strategic priorities into actionable plans and measurable outcomes. 

• Lead cross-functional initiatives that support organizational growth, sustainability, and program excellence. 

• Prepare executive briefs, dashboards, and materials for Executive leadership and board engagement. 

• Coordinate follow-through on CEO, board, and funder priorities. 

• Support operational efficiency, systems improvement, and change management. 

• Provides decision support to the CEO and Executive Leadership Team through analysis, synthesis of information, and preparation of executive recommendations.

• Helps identify emerging organizational risks and implementation challenges and elevates them to the CEO for consideration.

• Supports alignment of internal communications to ensure consistency with organizational priorities, values, and strategic direction.

• Supports the establishment of executive and cross-functional rhythms, including planning cycles, leadership meetings, and progress reviews. 

• Reinforces organizational culture, values, and accountability through executive-level collaboration and leadership practices.

• Leads or supports special strategic initiatives as delegated by the CEO that advance organizational priorities.

• Represent the CEO internally and externally as needed.

• Owns and strategically manages the CEO’s calendar to ensure time is allocated in alignment with organizational priorities, strategic goals, and impact.

• Evaluates all calendar requests through a strategic lens, balancing external obligations, internal leadership needs, and focused work time.

• Prepares the CEO for all meetings by ensuring agendas, objectives, and relevant materials are clear in advance.

• Serves as a bridge between the CEO and senior leadership, ensuring clarity, consistency, and accountability in decision-making and execution.

• Determines which meetings require CEO involvement and which can be delegated, deferred, or resolved independently.

• Ensures meetings drive progress rather than information sharing alone.

• Ensures consistent messaging across departments and prevents misalignment or duplication of effort.

• Manages relationships with senior staff, board members, and external partners on behalf of the CEO as requested.

• Ensures issues are properly framed and solutions proposed before reaching the CEO.

• Perform other duties and responsibilities as assigned by the Chief Executive Director, supporting organizational priorities and strategic initiatives.

  QUALIFICATIONS: 

• Educational Requirements: Bachelor’s degree required; Master’s degree in Education, Youth Development, Public Administration, Social Work, or a related field preferred.

• Professional Experience: Minimum of 5–7 years of experience in youth development, afterschool programming, or community school leadership, including at least 3 years in a supervisory or management role.

• Systems Knowledge: Experience in youth development, education, or government-funded nonprofits preferred.

• Communication Skills: Strong project management, communication, and relationship-building skills. Strong written and verbal communication skills, with the ability to present information clearly to internal teams, school partners, and external stakeholders.

• Relationship-Building: Demonstrated ability to build and maintain positive relationships with diverse stakeholders, including school leaders, staff, families, community partners, and funders.

• Technical Proficiency: Proficiency with Microsoft Office Suite (Outlook, Excel, Word), Google Workspace, DYCD Connect, and other data management platforms.

  WORKING CONDITIONS:

• The position is based in New York City and requires regular travel across the boroughs.

• Must be comfortable working in NYC Department of Education school buildings as well as various community-based locations.

• Ability to work occasional evenings and weekends to support events or special program needs.

• Occasional work travel as assigned for conferences, briefings and partnership trips.

• Must be able to navigate stairs and lift or carry materials weighing up to 25 pounds as needed.

  COMPETENCIES   
  Strategic Leadership & Execution
  • Ability to translate vision, strategy, and board priorities into clear plans, timelines, and outcomes.

• • Strong analytical and critical-thinking skills to assess complex organizational challenges and recommend solutions.
  • Proven capacity to manage enterprise-level initiatives from concept through execution.

  Executive Partnership & Judgment

  • Demonstrated ability to serve as a trusted advisor to Executive leadership with sound judgment and discretion.
  • Skilled in anticipating CEO needs, identifying risks, and proactively resolving issues.
  • Ability to handle sensitive and confidential information with integrity and professionalism.

  Organizational & Operational Effectiveness

  • Strong understanding of nonprofit operations, including programs, finance, fundraising, and compliance.
  • Experience improving systems, processes, and workflows to increase efficiency and accountability.
  • Ability to manage competing priorities while maintaining attention to detail and follow-through.

  Cross-Functional Collaboration

  • Skilled in working across departments to align teams around shared goals and outcomes.
  • Ability to influence without authority and build trust among diverse stakeholders.
  • Experience facilitating leadership meetings, retreats, and collaborative planning processes.

  Communication & Executive Presence

  • Exceptional written and verbal communication skills, including executive briefs, presentations, and board materials.
  • Ability to communicate clearly with staff, board members, funders, and external partners.
  • Strong executive presence with the ability to represent the CEO and organization effectively.

  Cultural Competency & Equity Commitment

  • Demonstrated ability to work effectively with individuals from diverse cultural, racial, and socioeconomic backgrounds.
  • Commitment to equity, inclusion, and mission-driven leadership.
  • Ability to reinforce organizational culture, values, and accountability across teams.

  Adaptability & Resilience

  • Flexibility to operate in fast-paced, evolving environments with shifting priorities.
  • Ability to remain calm and effective under pressure and during periods of organizational change.
  • Resilience and problem-solving mindset when navigating ambiguity or complexity.

  EQUAL OPPORTUNITY EMPLOYER 

  We are an equal opportunity employer, and all qualified candidates will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status, or any other characteristic protected by law.  

  We are committed to creating a diverse and inclusive workplace where all employees feel welcome and valued. We believe that diversity and inclusion are essential to our success in serving youth. 

  DISCLAIMER  

  This job description is intended to provide a general overview of the position and its essential functions. It is not intended to be an exhaustive list of all the duties and responsibilities that may be assigned to the staff member. The specific duties and responsibilities of the position may change from time to time, as determined by the needs of the organization. 

  The staff member must be able to perform the essential functions of the position satisfactorily, with or without reasonable accommodations. Reasonable accommodations will be made to enable employees with disabilities to perform the essential functions of their job, absent undue hardship.