Program Director – Job Opening

Program Director

Location: New York, NY (Harlem)

Type: Full Time, Exempt

About StreetSquash

StreetSquash was founded in Harlem in September 1999 as the second squash and education program in the United States. A comprehensive youth enrichment program, StreetSquash combines academic tutoring, squash instruction, community service, college preparation, leadership development, and mentoring for young people ages 11-24. What began as an after-school program with 24 middle school students and two staff members has expanded to serve 400 participants from 6th grade through college graduation, and entry into the workforce. Learn more about us at

About the Position

StreetSquash is seeking a demonstrated leader to fill the Program Director (PD) position. An ideal candidate will possess a passion for working with young people and driving an organization that supports participants on  the path to high school graduation, post-secondary education and completion, and securing meaningful, self-sustaining employment. The Program Director reports to the Deputy Director. 

Position Responsibilities 


  • Manage a team of full-time and part-time direct service staff, directly supervise department heads, overseeing both their performance and that of their teams
  • Assess staff strengths and provide regular, direct feedback regarding individual performance, areas for growth, and plans for improvement
  • In collaboration with the Manager of Operations & HR, support with talent management including: 
    • Recruitment and hiring of all program staff
    • Full-time staff evaluation timelines
    • Staff retention and appreciation initiatives
    • Staff performance plan implementation and termination procedures where appropriate


  • Work closely with the  Deputy Director to drive the programmatic vision and program development
  • Oversee development and implementation of all program areas (academics, college access, success, and alumni support, and social work) to ensure rigor, consistency, high-quality programming and mission alignment
    • Develop a deep understanding of the components of each aspect of program, the skills necessary to perform each job well, and the appropriate standard of performance for each role
    • Seek support and professional development in areas in which person is not already an expert
  • Observe and participate daily in programming, maintaining a consistent presence with students and staff
  • Ensure full participant enrollment and high attendance to achieve full space utilization and maximum impact
  • Oversee all programmatic components and support staff with logistics related to travel,  external opportunities, and hosting large events
  • Lead summer program planning, including curriculum development, staffing, and participant recruitment 
  • Maintain relationships with partner schools to ensure consistent flow of participants and organizational integration into school community

Virtual Programming

  • Oversee the development and implementation of all program areas, now being done remotely, ensuring excellent quality and rigor
  • Develop and monitor implementation and project plans for virtual program development; work closely with the executive management team to guide the design of remote instruction programs and the conversion of existing in-person offerings


  • Coordinate all building and staff scheduling and program logistics
  • Oversee program budget in conjunction with  Deputy Director and Finance Department
  • Collaborate with the Manager of Operations & Human Resources to ensure staff adherence to data management systems in order to generate accurate data and program insights
  • Collaborate with the Development and Communications Department to support the creation of organizational collateral, partnership-building, and stewardship
  • Track and analyze participant enrollment data and trends for StreetSquash related to student persistence, success, graduations, and post-secondary engagement


The Program Director will be expected to oversee and be present at weekday practices until 6:30/7:00 pm, frequent Saturday programming, and all special events. This individual sets the tone for hard work and commitment, with a consistent presence in programs and willingness to work any hours that are required. The Program Director is responsible for ensuring that StreetSquash continues to thrive and serve its constituents well. It is a unique opportunity for a talented and focused individual to serve as a critical leader and to make a difference in the lives of the program’s participants.


  • Graduate degree or Bachelor’s degree with 7+ years of relevant experience (degrees in Education, Non-Profit Management, Social Work, or Counseling preferred)
  • 7+ years of experience in a youth-focused not-for-profit with 3+ years management experience, including managing teams of 4+ 
  • 7+ years direct service experiences with middle and high-school-aged students 
  • Experience managing day-to-day operations, developing and implementing programs, developing partner collaborations, and working with a range of community groups
  • Proven track record with managing  multiple projects, planning backwards and anticipating obstacles, identifying and involving stakeholders appropriately, using resources wisely, and being flexible and adaptable under pressure
  • Sensitivity to different cultures and communities;  Demonstrated ability to work well with diverse or marginalized populations; can bring in allies across diverse communities

Qualifications & Experience

  • Experience in managing employees in multiple different roles and providing performance feedback and role support
  • High level strategic thinking and planning
  • Solid organizational abilities, including planning, program development and task facilitation
  • Able to understand program data and the purpose of its usage; Use data to identify programmatic trends and develop responsive practices for improving programs
  • Clear and compelling in both verbal and written communications, enjoys motivating a team around a common goal
  • Strong executive presence with an ability to facilitate and lead meetings and trainings
  • A strong collaborator who enjoys learning and developing best practices in partnership with a team, implementing processes, and refining existing processes
  • Ability to establish and strengthen relationships with participants and partners
  • Proven ability to make good, proactive decisions in potentially emotionally-charged situations and/or in the absence of complete clarity; comfortable taking risks
  • Passion for young people and enjoyment of spending time with them, coaching or tutoring them, and pushing them to set and achieve goals in all aspects of their lives
  • Spanish proficiency a plus
  • Google Suite, Zoom, and Salesforce experience a plus or demonstrated experience to learn new systems


StreetSquash values long-term, deep, impactful work with participants. It takes years to cultivate strong, positive relationships, and staff retention is a critical component of organizational success. This is not a transitional role or a stepping stone. Candidates should be prepared to commit to StreetSquash for several years. 

Compensation & Benefits

StreetSquash offers competitive compensation, commensurate with experience. Full benefits include employer-supported health coverage, monthly MetroCard, monthly cell phone stipend, 20 days of paid vacation, 40 hours of accrued sick time, 3 personal days (after the first 90 days), and 401k contributions (after 1 year of employment).

Application Process

Interested candidates should send a resume and a detailed cover letter that directly addresses the specified requirements as outlined above and why you are interested in this position to with Program Director Position in the subject line. Only complete applications will be reviewed and only shortlisted candidates will be contacted. There will be three rounds of interviews, via phone and Zoom. After each round, the hiring team will notify candidates if they will be invited back. Final applicants will be requested to consent to a pre-employment background check. A background check is required to extend a job offer.