Chief of Staff to the CEO

Roads to Success Inc•New York, NY

5d•$90,000 - $110,000

About The Position

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.

Requirements

Bachelor’s degree required; Master’s degree in Education, Youth Development, Public Administration, Social Work, or a related field preferred.
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.
Experience in youth development, education, or government-funded nonprofits preferred.
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.
Demonstrated ability to build and maintain positive relationships with diverse stakeholders, including school leaders, staff, families, community partners, and funders.
Proficiency with Microsoft Office Suite (Outlook, Excel, Word), Google Workspace, DYCD Connect, and other data management platforms.

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.