Roads to Success · 15 hours ago
Chief of Staff to the CEO
New York, NY
Full-time
Onsite
Lead/Staff, Director/Executive
$90K/yr - $110K/yr
5+ years expRoads to Success is a youth development organization focused on empowering young people to take control of their future. They are seeking a strategic Chief of Staff to partner with the CEO, ensuring alignment between strategy and operational execution while supporting organizational growth and efficiency.
Corporate TrainingEducationProfessional ServicesTraining
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
Qualification
Required
Bachelor's degree required
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
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
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
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
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
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
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
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
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
Preferred
Master's degree in Education, Youth Development, Public Administration, Social Work, or a related field preferred
Experience in youth development, education, or government-funded nonprofits preferred
Company
Roads to Success
Roads to Success is a integrated academic and recreational after-school and summer programs for schools, communities and agencies.
51-200 employees
Funding
Current Stage
Growth StageLeadership Team
Sheila Duke
Chief Executive Officer
Esther Kuykendoll
Chief Administrative Officer (CAO)
Recent News
Company data provided by crunchbase