Senior Director of Learning

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.