[School Year 2026-2027] Middle School Assistant Dean of Student Life

New York, NY - Multi-SiteFull-Timemid

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Overview

Originally founded in 1991 as Harlem RBI, DREAM has grown to annually serve more than 2,500 youth across East Harlem and the South Bronx through a network of seven PreK-12, extended-day, extended-year DREAM Charter Schools and community sports-based youth development programs.

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Originally founded in 1991 as Harlem RBI, DREAM has grown to annually serve more than 2,500 youth across East Harlem and the South Bronx through a network of seven PreK-12, extended-day, extended-year DREAM Charter Schools and community sports-based youth development programs. Through our commitment to rigorous academics, social-emotional learning, deep family and community engagement, and health and wellness, we create lifelong learners who are equipped to fulfill their vision of success in and out of the classroom. We dream big, as well, with an aggressive five-year plan to expand to serve 3,500 students across seven schools—growing our organization’s impact and leveling the playing field for all children. To learn more, visit wearedream.org.

The Assistant Dean of Student Life is responsible for supporting DREAM’s after-school, summer, enrichment, and athletic programs and driving positive culture and outcomes for students and families at their school. Reporting to the Dean of Student Life, this role will be responsible for supporting the design and implementation of high-quality after-school, summer, enrichment, and recess programming as part of DREAM’s Grow the Whole Child model.

Manage and organize the daily operations of youth development programming to ensure that youth participate in activities safely, on schedule, and with adequate supplies and services;

Lead and execute programming independently when the Dean of Student Life is out or unavailable;

Support the Dean of Student Life in developing and maintaining strong school-based and external partnerships;

Support the Dean of Student Life in coaching and developing after-school, summer, and athletics program part-time staff;

Under the supervision of the Dean of Student Life, plan and lead daily team meetings (huddles) before the program begins, focused on professional development for staff, updates, and other relevant topics to ensure communication and expectations are clear.

Manage data collection and record-keeping to ensure accurate reporting and compliance with specific grant requirements;

Manage incident protocols, communication, and school-leader collaboration for incidents in programming;

Collaborate with the program leadership team to research and develop new programming ideas to engage youth and further program goals.

Lead efforts to ensure that recruitment, retention, and communication goals of after-school and summer programs are satisfied and maintain accurate youth records;

Build relationships with families and promote family involvement in programs and overall school culture.

Establish a campus culture that emphasizes respect, teamwork, effort, and critical thinking;

Promote DREAM’s mission, values and organizational policies to all program staff and stakeholders.

At minimum, a High School Diploma and 6+ years of experience in a youth services field; or an Associate's Degree and 5+ years of experience in the youth services field; or a Bachelor's Degree and 3+ years of experience in a youth services field;

At least two years of experience directly managing a youth services program, after-school program, and/or summer youth program, including leading planning and development, required;

Successful track record of coaching and supervising staff towards meeting programmatic goals;

Demonstrated experience in developing and managing partnerships with youth services organizations and/or other charter networks;

Excellent oral and written communication skills, organization skills, and attention to detail;

Bilingual (English/Spanish) a plus;

Strong fluency in Google Suite (docs, slides, sheets, etc.);

Understanding of opportunities and challenges in the lives and education of urban youth;

A desire to make a difference in the lives of our scholars, families, and community;

Deep embodiment of DREAM’s organizational values of teamwork, diversity, integrity, and fun.

We offer comprehensive benefits including:

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.

Benefits are subject to change.

Start Date: 7/1/2026

Hours are 9:00am-6:00pm, five days a week

On-site work at one of our Middle School sites in East Harlem and the South Bronx

DREAM offers a competitive salary commensurate with relevant experience with the potential for an annual performance-based increase. The incoming salary range for this position is $65,000 to $75,000 per year. New hires are typically brought into the organization at a salary closer to the start of the range depending on qualifications, internal equity, and the budgeted amount for the role. All staff are eligible for annual performance-based increases. Because we value staff tenure in each role, we do not currently cap salary ranges.