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About the Role

The Senior Director of Learning will lead the design and implementation of high-priority initiatives across DREAM’s K–12 Learning Team, translating ambitious ideas into actionable initiatives that strengthen the organization's grow-the-whole-child model and improve student outcomes. This leadership role aligns strategic vision with execution by organizing stakeholders and managing cross-functional partnerships.

Responsibilities

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, and AI.
Design initiatives from the ground up, including defining the problem, establishing a theory of action, crafting recommendations, and developing an implementation path.
Establish measurable goals, objectives, KPIs, and progress-monitoring benchmarks.
Develop clear recommendations, decision-making materials, and executive-level communications.
Build trusting relationships with internal and external stakeholders including funders, grant partners, and consultants.
Lead complex, high-priority initiatives from launch through full implementation with independence and accountability.
Create and implement structures for successful execution, including project plans, implementation calendars, and accountability systems.
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 for initiatives to transition into sustainable, organization-wide practices.
Serve as a strategic partner to the Deputy Chief of Learning, coordinating priorities and cross-functional work.
Convene and lead cross-functional working groups and task forces.
Build trusting relationships across all teams and levels of the organization.
Serve as a conduit between the Learning Team and external stakeholders.
Represent DREAM in high-stakes external partnerships.
Flex across Learning Team priorities as organizational needs evolve, taking ownership of new or ambiguous projects.
May take on direct reports, responsible for coaching, developing, and managing them.

Requirements

Bachelor’s degree required; advanced degree in Education, Business, or a related field preferred.
Minimum 8 years of experience in education.
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, with high organization and attention to detail.
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 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).
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 students, families, and the community.

Skills

Relational influence
Change management
Adult learning theory
K-12 academics
Special education
Social-emotional learning
Mental health
Extracurricular programming
Athletics
Arts
Collaborative spirit
Interpersonal skills
Written communication
Verbal communication
Google Suite
Data analysis
Project management tools

Location

East Harlem
South Bronx

Work Type

Hybrid (3 days in office, up to 2 days remote)

Experience Level

Minimum 8 years of experience in education
At least 3 years of experience as a senior leader

Education Level

Bachelor’s degree required
Advanced degree in Education, Business, or a related field preferred

Salary/Compensations

$145,000 to $160,000

Benefits

Flexible Medical Health Plans
Dental and vision plans
Disability benefits
Life insurance
Up to 12 weeks fully paid Parental Leave
Flexible spending account options
Pre-tax commuter benefits
Fitness and entertainment discounts
Employee assistance program (EAP)
403(b) retirement plan with employer match
Referral, performance, and tenure milestone bonuses
Discounted school meals
Tuition reimbursement support
Access to a professional development fund
Approximately 48 days off throughout the school year for 12-month employees

About the Company

Founded in 1991 as Harlem RBI, DREAM serves over 2,500 youth annually across East Harlem and the South Bronx through PreK-12 schools and sports-based youth development programs.
DREAM focuses on rigorous academics, social-emotional learning, family and community engagement, and health and wellness to create lifelong learners.
The organization has an aggressive five-year plan to expand to serve 3,500 students across seven schools.
DREAM aims to level the playing field for all children.

Equal Opportunity

At DREAM, diversity, equity, and inclusion are a matter of mission.
DREAM is committed to building a team where each individual can bring their full identity and experience to work because representation matters.
DREAM engages staff that represent and appreciate the diversity of our majority Black and Hispanic student body.
DREAM is 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.
DREAM provides reasonable accommodations for qualified individuals with disabilities in accordance with the Americans with Disabilities Act and applicable state and local laws.