[School Year 2026-2027] Dean of Student Life

DREAM • New York, NY

1d • Onsite

About The Position

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.

Requirements

• Bachelor’s degree, required (preferably in education, social work, youth development or related field);
• 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;
• 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 professionalDevelopments and providing coaching and feedback that leads to improved professional outcomes;
• 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 school classroom management and instructional strategies;
• The ability to manage behaviors using positive youth-development principles (experience with restorative justice practices strongly preferred);
• A strong belief in the mission and values of DREAM, including the desire to make a difference in the lives of our students, families, and community;
• Exemplary interpersonal skills;
• Strong written and oral communication skills;
• Excellent organizational and problem solving skills;
• Air-tight follow up and follow through;
• Ability to plan at the systems level and make these plans a reality by leading through others;

Nice To Haves

• advanced degree in an education field, preferred

Responsibilities

• 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 (Middle School, only).
• 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.

Benefits

• Flexible Medical Health Plans, subsidizing the majority of costs for the employee, their spouse/domestic partner and children;
• The ability to select between a variety of medical plans according to what best suits the employee’s needs;
• Dental and vision plans;
• Disability benefits;
• Life insurance;
• Up to 12 weeks fully paid of Parental Leave;
• Flexible spending account options;
• Pre-tax commuter benefits (parking and transit);
• Fitness and entertainment discounts;
• A variety of support through our employee assistance program (EAP);
• 403(b) retirement plan with employer match starting at 4% after one year, with increases tied to DREAM tenure;
• Referral, performance, and tenure milestone bonuses;
• Discounted school meals through our in-house Scratch Food Program;
• Tuition reimbursement support;
• Access to a professional development fund;
• School-based 12-month employees have approximately 48 days off throughout the school year including holidays, school breaks, personal days, and wellness days.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level