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Middle School Dean of Student Life

Job in New York, New York County, New York, 10261, USA
Listing for: Wearedream
Full Time position
Listed on 2026-07-09
Job specializations:
  • Education / Teaching
    After School, Education Administration, Youth Development
Salary/Wage Range or Industry Benchmark: 100000 - 116000 USD Yearly USD 100000.00 116000.00 YEAR
Job Description & How to Apply Below
Location: New York

Reporting to the school Principal, the Dean of Student Life is responsible for leading DREAM’s after-school, summer, enrichment, and athletic programs and driving positive culture and outcomes for students and families at their school site. This role is critical to ensuring the success of DREAM’s Grow the Whole Child Model and is responsible for ensuring each DREAM student has access to high quality enrichment and extended-day, extended-year programming.

The ideal candidate is a reliable team player with deep expertise in and commitment to positive youth development.

After School, Summer, and School-Day Enrichment
  • Lead execution of after-school, summer, and school‑day enrichment, recess, and athletic programs to ensure high‑quality programming and strong outcomes at school site;
  • Lead outreach and process for enrollment and participation in after‑school and summer program with participants, families, and staff;
  • Lead the professional development of staff in after‑school, recess, summer and athletics programming, including real‑time coaching and feedback;
  • Serve as primary instructional coach for full‑time school‑day, after‑school and summer enrichment (music, art, PE, dance, musical theater, etc.) teachers;
  • Regularly review enrichment lesson plans, observe enrichment teachers and provide enrichment teachers with timely, highest‑leverage, actionable feedback;
  • Supervise Assistant Dean of Student Life to support the design and implementation of programming;
  • Design and lead execution of all site‑level structures, procedures, and protocols for after‑school, summer, recess, and school‑day enrichment programs, in consultation with school Principal;
  • Train and coach staff to ensure fidelity to network after‑school, summer, and enrichment curriculum;
  • Partner with the Talent team to recruit, hire, and onboard staff;
  • Manage execution of competitive athletics programming
Management and School Leadership
  • Serve as a key member of the School Leadership Team, collaborating with the Principal and other members of the School Leadership Team to ensure alignment between school‑day, after‑school and summer to maximize the impact of extended‑day, extended‑year programming;
  • Collaborate with network leaders to design and implement high quality curriculum and programming that drives student social‑emotional learning outcomes, academic outcomes, and physical activity outcomes;
  • Develop and monitor effective systems to ensure accurate reporting and compliance with specific grant requirements and network data reporting requirements;
  • Ensure all incident protocols are followed and reporting and communication is completed in a timely manner for all areas of responsibility;
  • Hire and manage after school, summer, and athletics part‑time staff;
  • Collaborate with the Student Life team and Principal to strengthen school culture through attendance accountability, infusing joy into school life, and supporting implementation of positive youth development practices;
  • Create coverage plans as needed for all areas of responsibility (after‑school, summer, recess, and enrichment);
  • Conduct walkthroughs, review student and school data, and drive changes as needed to improve student outcomes.
Degree & Experience
  • Bachelor’s degree, required (preferably in education, social work, youth development or related field); advanced degree in an education field, preferred;
  • At least 5 years of leading and managing youth development programming, highly preferred;
  • At least 3 years of people leadership and management experience, highly preferred;
  • Experience working in K‑12 Charter Schools, highly preferred;
People Management & Development
  • Expertise in managing entry‑level staff or working closely with high‑school and college‑aged students;
  • Track record of success in developing others, including designing and leading group professional developments and providing coaching and feedback that leads to improved professional outcomes;
Domain Knowledge & Practical Expertise
  • Ability to use data‑driven practices to improve youth outcomes;
  • A strong understanding of how explicit and embedded SEL competency‑building positively impacts academic achievement;
  • Extensive knowledge of best practices in…
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