---
title: 'Senior Director of Learning at DREAM'
canonical: 'https://feeny.ai/job/senior-director-of-learning-dream-new-york-hrxhap9h9p5s'
type: 'job'
last_seen: '2026-09-13'
---

# Senior Director of Learning at DREAM

- **Company:** DREAM
- **Location:** New York, NY
- **Employment:** full-time
- **Work type:** hybrid
- **Posted:** 2026-08-04
- **Last confirmed live:** 2026-09-13
- **Apply:** https://jobs.lever.co/wearedream/5b584536-51ac-4b83-b083-8f8620c24280

## Job description

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.

Reporting directly to the Deputy Chief of Learning, the Senior Director of Learning will lead the design and implementation of high-priority initiatives across DREAM’s K–12 Learning Team. The Senior Director is charged with translating ambitious ideas into clear, actionable, and sustainable initiatives that strengthen DREAM’s grow-the-whole-child model and improve outcomes for students. This leadership role will align strategic vision with day-to-day execution through organizing stakeholders around complex initiatives and managing cross-functional partnerships. This is an exciting opportunity for a mission-driven, highly adaptable leader with a strong background in school or network leadership, the ability to coach and develop leaders, expertise in designing and facilitating strong professional learning, a record of developing initiatives from the ground up, a genuine curiosity and excitement to learn new content and turn mess into success, and the ability to drive complex work through influence, relationships, and cross-functional partnerships.

## Responsibilities

Initiative Design

- Lead the development of high-priority Learning Team initiatives related to academics, special education, social-emotional learning and mental health services, extended learning and enrichment (after-school, summer, and school day enrichment) and AI (examples of initiatives may include running an edtech pilot program in one school, coordinating a special education-academics working group, redefining the network structure for managing RTI systems across social-emotional learning, mental health, behavior, attendance, and academics, working with an external consultant, grant partner, and network academics leaders to develop a STEM leader fellowship, leading a task force to align debate skills in our history curriculum to our extracurricular debate programs, etc.);
- Design initiatives from the ground up, including defining the problem through root cause analysis, establishing a theory of action, crafting evidence-based recommendations, and developing a clear path from concept to implementation;
- Establish measurable goals, objectives, KPIs, and progress-monitoring benchmarks to assess implementation quality and impact on student and school outcomes;
- Develop clear recommendations, decision-making materials, and executive-level communications that enable senior leaders to move initiatives forward;
- Build trusting relationships with internal and external stakeholders including funders, grant partners, and consultants who partner with us on initiative design and implementation.

Initiative Implementation

- Lead complex, high-priority initiatives from launch through full implementation, operating with significant independence and accountability for successful outcomes and excellence in implementation;
- Create and implement structures necessary for successful execution, including project plans, implementation calendars, meeting cadences, accountability systems, and progress-monitoring tools;
- Coach school and network leaders to understand, adopt, and execute new initiatives;
- Monitor initiative implementation progress and outcomes and adjust as necessary;
- Capture and communicate successes and impact to broad audiences;
- Establish systems and documentation that enable initiatives to transition from launch-stage projects to sustainable, organization-wide practices executed by others.

Cross Functional Leadership

- Serve as a strategic partner to the Deputy Chief of Learning, helping coordinate priorities and cross-functional work across the Learning Team;
- Convene and lead cross-functional working groups and task forces, ensuring clear goals, productive collaboration, and consistent follow-through;
- Build trusting relationships quickly across all teams and levels of the organization in order to move complex work forward;
- Serve as a conduit between the Learning Team and external stakeholders;
- Represent DREAM in high-stakes external partnerships and ensure successful partner relationships;
- Flex across Learning Team priorities as organizational needs evolve, taking full ownership of new or ambiguous projects with limited direction;
- As the Learning Team structure evolves, may take on ~two direct reports and will be responsible for coaching, developing, and managing them toward strong individual and team outcomes.

Other responsibilities related to the role as assigned.

## Qualifications

- Bachelor’s degree required; advanced degree in Education, Business, or a related field preferred;
- Minimum 8 years of experience in education, with at least 3 years of experience as a senior leader at a charter school or network (i.e., Principal, Network Director, etc.) and/or education consulting working closely with charter schools;
- Demonstrated success leading complex, cross-functional initiatives;
- Expert in best practices for relational influence, change management, and adult learning theory;
- Ability to keep the big picture at the forefront, while bringing a high degree of organization and attention to detail, with the capacity to manage multiple priorities and meet tight deadlines;
- Working fluency and knowledge of K-12 academics, special education, adult learning, research-based pedagogy, social-emotional learning, mental health, extracurricular programming, athletics, and the arts;
- Strong collaborative spirit and interpersonal skills, with the ability to build trusting relationships in a fast-paced environment;
- Impeccable integrity, discretion, and the ability to handle confidential information sensitively;
- Excellent written and verbal communication skills, including ability to convey complex information to a variety of audiences;
- Fluency with Google Suite (Docs, Sheets, Slides) and aptitude for data analysis, familiarity with Asana or other project management tools;
- Demonstrated resourcefulness, flexibility, and a positive, solutions-oriented mindset.
- 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.

Working Expectations This role is part of the Learning Team, which currently works 3 days in the office and up to 2 days remote, per week (subject to change). Some weeks will require more in-person work.

## Benefits and Paid Time Off

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.

## Compensation

DREAM offers a competitive salary commensurate with relevant experience. The incoming annual salary range for this position is $150,000  to $160,000. 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 regular employees receive annual compensation increases and have the opportunity to earn both performance- and tenure-based bonuses. Because we value tenure in each role, our salary ranges are not capped.

Our Commitment to Diversity, Equity, and Inclusion

At DREAM, diversity, equity, and inclusion are a matter of mission.

From our schools to our playing fields, DREAM is committed to building a team where each individual can bring their full identity and experience to work because representation matters—it enriches our team culture, enhances our ability to innovate, and strengthens our impact in and out of the classroom. DREAM engages staff that represent and appreciate the diversity of our majority Black and Hispanic student body, while working to ensure that our practices are equitable, welcoming, and productive. We are dedicated to creating a world where youth, especially youth of color, have permission to dream—along with the tools and opportunities to make their dreams reality.

Come dream with us.

DREAM Maxims

All Kids Can. This Kid Can. DREAM is Family. Fun is a Serious Value. Teamwork Makes the DREAM Work. Fail. Persist. Exceed. DREAM Big.

Applying to DREAM

We know applying for a new job can be a daunting process. In addition, studies have shown that historically underrepresented individuals often only apply to roles if they meet 100% of the qualifications. We encourage all applications! You may be just the person we need. If you have any questions about your application or interview process, do not hesitate to ask your recruiter; we are here to help!

DREAM provides reasonable accommodations for qualified individuals with disabilities in accordance with the Americans with Disabilities Act and applicable state and local laws. If accommodation is needed to participate in the job application or interview process, please contact your recruiter.

If you are a current DREAM employee, please click here to review our Internal Selection Process before applying.

## About DREAM

## Company Overview
- **One-liner**: DREAM is a nonprofit organization that provides comprehensive education and youth development programs through a network of free charter schools and community-based programming in East Harlem and the Bronx.
- **Entity Type**: Private (nonprofit)
- **Headquarters**: New York, New York, United States
- **Founded**: 1991
- **Founders**: Founded by a group of volunteers (originally as Harlem RBI); current leadership includes co-CEOs Richard Berlin and Eve Colavito.

## Core Business
- **Primary Industry**: Education (K-12 charter schools, afterschool and summer programming, postsecondary support)
- **Target Customers**: Students and families in underserved communities (predominantly East Harlem and the Bronx); B2C (direct to students/families)
- **Mission Statement**: “DREAM ensures that all young people recognize their potential and realize their dreams.” ([wearedream.org](https://wearedream.org/our-mission-maxims/))

## Products & Services
- **DREAM Charter Schools**: Tuition-free, extended-day, extended-year public charter schools serving Pre-K through 12th grade across three campuses. The model includes small group instruction, two teachers per classroom, rigorous academics, social-emotional learning, and AP classes for all.
- **Afterschool & Summer Learning**: Approximately 600 annual hours of afterschool programming and 300 hours of summer programming, covering arts, athletics, STEM, and technology.
- **Postsecondary & Career Pathways (Legends)**: Up to six years of formal college and career support for alumni, including college access counseling, scholarships, career exploration, and work experiences.

## Market Standing
- **Valuation / Market Cap**: Not applicable (nonprofit). Annual operating budget of ~$66M (2024), projected to grow to $100M by 2028 ([DREAM Strategic Plan](https://wearedream.org/wp-content/uploads/2026/03/2024-2028-Strategic-Plan-FOR-USE.pdf)).
- **Key Metric**: Annual revenue of $35.9M (estimated, per LinkedIn/Growjo data) ([linkedin.com](https://linkedin.com/company/wearedream)).
- **Notable Investors / Partners**: Not publicly disclosed; the strategic plan highlights partnerships with community-based organizations to provide social services and expanded electives.
- **Growth Signals**:
  - Headcount of 311 employees (+21.7% YoY); 9,915 LinkedIn followers (+21.7% yearly) ([linkedin.com](https://linkedin.com/company/wearedream)).
  - 2,800 students served across three sites in East Harlem and the Bronx.
  - 100% high school graduation and college acceptance rates among seniors.
  - Plans to grow to 7 schools across 3 permanent campuses by 2028.

## Competitive Advantages
- **Holistic Whole-Child Model**: Combines rigorous academics, social-emotional learning, physical/mental health, and deep family engagement, all under one roof with extended hours.
- **Long-Term Commitment**: Supports students from Pre‑K through age 24, including postsecondary counseling and career pathways – rare among charter networks.
- **Inclusive Excellence**: Nearly one‑third of students have special needs; 9 in 10 live below the poverty line; the model is designed to close opportunity gaps while maintaining high achievement.
- **Community Roots**: Originated as a grassroots baseball program (Harlem RBI) in 1991, giving it deep trust and embeddedness in East Harlem and the Bronx.

## Strategic Focus
The 2024‑2028 strategic plan, *Bending the Arc*, lays out three pillars:
1. **Grow Our Impact** – Accelerate student learning (especially STEM and special education), evolve high school programming, expand electives/extracurriculars, and build career-connected learning.
2. **Invest in People** – Attract and retain diverse talent, strengthen leadership pipelines (aim for 20% of roles filled by alumni), and deepen family partnerships.
3. **Build for Future Dreams** – Strengthen financial sustainability (80% of revenue from public funding), improve systems and business efficiency, and ensure equitable resource allocation.

## Why Work Here
- **Mission-Driven Culture**: Employees work directly to level the playing field for underserved youth; the organization is committed to equity and representation (“each individual can bring their full identity and experience to work”).
- **Growth and Stability**: Headcount has grown 21% in the last year; the organization plans to add 150+ full-time roles over the next five years, with a stated goal of filling a majority of leadership positions through internal promotions.
- **On-Site, Community-Focused Roles**: Positions are based at school campuses in the Bronx and East Harlem (on‑site, not remote). Typical roles include teachers, deans, operations coordinators, and family services staff.
- **Employee Sentiment**: Glassdoor‑style rating of 3.3/5.0 (166 reviews) on LinkedIn. Culture scores highest (3.7), while work‑life balance (2.8) and compensation (3.5) are lower – typical for mission‑driven education nonprofits.
- **Perks & Benefits**: Not detailed publicly, but the strategic plan emphasizes “a compelling employee experience” and an 80% staff retention target.

## Sources
1. [DREAM – Mission & Maxims](https://wearedream.org/our-mission-maxims/)
2. [DREAM – Our Leadership](https://wearedream.org/our-leadership/)
3. [DREAM 2024‑2028 Strategic Plan](https://wearedream.org/wp-content/uploads/2026/03/2024-2028-Strategic-Plan-FOR-USE.pdf)
4. [DREAM LinkedIn Company Profile](https://linkedin.com/company/wearedream)
5. [DREAM Career Page (Lever)](https://jobs.lever.co/wearedream/)

## Other roles at DREAM

- [Coach with DREAM Charter School [Resume Drop] – Assistant Coach Opportunities](https://feeny.ai/job/coach-with-dream-charter-school-resume-drop-assistant-coach-opportunities-dream-b889e6s8y9bx) — New York, NY
- [Coach with DREAM Charter School [Resume Drop] – Head Coach Opportunities](https://feeny.ai/job/coach-with-dream-charter-school-resume-drop-head-coach-opportunities-dream-new-bcanvwvqhb4d) — New York, NY
- [Part-Time Cook](https://feeny.ai/job/part-time-cook-dream-new-york-z8n4nrjetwg9) — New York, NY
- [[2026-2027] Temporary Assistant Dean of Culture](https://feeny.ai/job/2026-2027-temporary-assistant-dean-of-culture-dream-bronx-vjepr0awpa8z) — Bronx, NY
- [Central Office Operations Coordinator](https://feeny.ai/job/central-office-operations-coordinator-dream-new-york-v2c8f9gawkzh) — New York, NY
- [High School AP Biology and AP Environmental Science Teacher](https://feeny.ai/job/high-school-ap-biology-and-ap-environmental-science-teacher-dream-bronx-a8pdf8fr7pen) — Bronx, NY
- [Middle School Social Studies Teacher](https://feeny.ai/job/middle-school-social-studies-teacher-dream-new-york-fmmphbf2jakp) — New York, NY
- [Part Time Supper Cook](https://feeny.ai/job/part-time-supper-cook-dream-bronx-ehpw2zr6nr1e) — Bronx, NY
- [High School Math Teacher](https://feeny.ai/job/high-school-math-teacher-dream-bronx-eczfk7fkqytn) — Bronx, NY
- [[Immediate Start] Youth Worker - High School](https://feeny.ai/job/immediate-start-youth-worker-high-school-dream-bronx-vkb4jpjszjxz) — Bronx, NY