Director of System Strategy

What We Do

At Leading Educators (LE), we know that excellent teaching is the most important driver of student success. The moment a student steps foot in the classroom, their opportunity to learn depends on how prepared their teacher is to translate complex content knowledge, standards, and their knowledge of that student into lessons that help them learn deeply and apply their thinking to the real world.

That’s a big lift, and it often happens alone. As a national nonprofit, we partner with school systems to overcome persistent instructional challenges, foster intentional collaboration and adult learning by design, and ignite new possibilities through systemic solutions at the intersection of teaching, talent, and technology.

We work shoulder-to-shoulder with educators at every level of the education system to strengthen their instructional and leadership practices, bring a vision for excellent instruction to life with consistency, and ensure every student reaches their full potential.

Through direct support, strategic advising, innovation pilots, and best-in-class research, we help educators work toward a future where every student is ready to thrive. Learn more about our work at leadingeducators.org.

Internal and External Candidate Application Deadline: 3/17/2026

Position

System-level instructional improvement requires more than good programs—it requires strategic vision, deep expertise, and the ability to guide district and state leaders through complex decisions about instruction, technology, and organizational alignment. As the Director of System Strategy, you'll lead targeted advisory engagements focused on strengthening instructional coherence and strategic system improvement within district and state partnerships.

This is a senior advisory and project leadership role where you'll work directly with superintendents, chief academic officers, and senior instructional leaders to assess system conditions, clarify strategic priorities, and translate those priorities into actionable plans. You'll bring deep instructional expertise in literacy or mathematics—with strong preference for mathematics—and combine it with sophisticated understanding of how technology, including AI, can be strategically leveraged to advance instructional goals.

A central responsibility of this role is integrating technology, including artificial intelligence, as a strategic lever for instructional improvement. You won't approach technology as an operational add-on or a compliance requirement. Instead, you'll guide system leaders in evaluating how technology investments and tools align to instructional goals, leadership capacity, and adult learning priorities. You'll engage in high-level conversations about subject-specific instruction while simultaneously analyzing and advising on the strategic use of technology to advance those goals. This requires the rare combination of deep instructional expertise and sophisticated understanding of how technology can meaningfully support—or hinder—instructional improvement.

You'll serve as the project lead from contract launch through completion, translating contracts into defined scopes of work, developing comprehensive project plans, coordinating cross-functional internal teams, and ensuring high-quality execution and deliverables. You'll operate with a high degree of autonomy, exercise sound judgment in ambiguous contexts, and build trusting relationships with senior leaders by quickly synthesizing context and reflecting back clear, decision-ready insights. Your work will contribute to codifying and improving Leading Educators' system advising practices while advancing real instructional improvement in the districts and states you serve.

Do you have expertise in…

• System-level instructional leadership and strategy, with demonstrated experience advising district and state leaders on instructional coherence, vision, and leadership practice?
• Mathematics instruction, with deep understanding of how students learn and what research tells us about effective teaching across systems?
• Technology strategy and evaluation, with ability to assess how technology investments—including AI tools—align to instructional goals, leadership capacity, and adult learning priorities, and to advise leaders on strategic technology integration rather than technology adoption for its own sake?
• Project leadership and client advisory, with strong project management skills, ability to translate high-level vision into structured plans, and demonstrated success building trusting relationships with senior stakeholders?

Do you enjoy…

• Leading high-stakes strategy conversations, where you synthesize complex context—instructional priorities, constraints, governance dynamics—and reflect it back as clear, decision-ready insights that move leaders forward?
• Bridging instruction and technology strategically, helping system leaders think deeply about how technology investments align to and support instructional priorities, rather than becoming operational distractions or solutions in search of problems?
• Evaluating technology through an instructional lens, assessing current and proposed tools against clear criteria—instructional use case, integration requirements, total cost, data and privacy constraints, and change-management load—to guide leaders toward coherent, purposeful technology portfolios?
• Managing complex projects from start to finish, translating contracts into scoped workplans, coordinating cross-functional teams, monitoring progress, and adjusting plans proactively to protect outcomes and timelines?

If you've answered affirmatively to these questions and meet the following prerequisites, we urge you to seize this opportunity. This role calls for the following:

• Minimum of 8 years of professional experience in system-level instructional leadership, strategy, or client-facing advisory roles
• Demonstrated expertise in mathematics instruction, with strong preference for mathematics experience
• Experience advising or working directly with district-level leaders on instructional coherence and strategy
• Experience leveraging technology, including AI, as a strategic lever to improve instruction, leadership, or system alignment—with demonstrated ability to evaluate technology investments and guide strategic decision-making aligned to instructional priorities
• Ability to engage in sophisticated conversations about both subject-specific instruction AND strategic technology use, understanding how to assess alignment between technology investments and instructional goals
• Strong project management and client relationship skills, with demonstrated ability to translate contracts into defined scopes of work and manage delivery from launch through completion
• Comfort navigating ambiguity, with proven ability to translate high-level vision into structured plans and success in building trusting relationships across a range of stakeholders
• AI Fluency at the Expert level—demonstrating deep understanding of how AI can be applied strategically within your function, selecting and optimizing AI tools, guiding others in effective use, understanding tradeoffs and risks, and helping shape how AI is embedded into team practices
• Ability to travel extensively (1–5 trips per month, depending on the time of year)

Travel Requirements

• This remote position requires high travel (1–5 trips per month, depending on the time of year).
• National travel for org retreats, programming, job related travel, or professional development 
• Outside of the above mentioned travel, this person will work from a home office that must be located anywhere within the U.S. 

Questions? We’re here to help.

If you have questions about this role or about our hiring process at any point, please don’t hesitate to reach out to us at talent@leadingeducators.org. This inbox is monitored regularly, and we aim to respond within two business days. To ensure your question receives a thoughtful and timely response, we kindly ask that you refrain from emailing individual staff members or members of our HR team directly. The best way to connect with us is always through talent@leadingeducators.org.

Why Work at Leading Educators? 

Imagine being part of an organization where your ideas and perspectives are highly valued. At Leading Educators, we believe in fostering individual strengths, encouraging personal growth, and embracing innovative ideas. If you thrive in a remote working environment, with the added excitement of travel, we're the perfect fit for you. By joining us, you become part of a powerful community of peers nationwide. Regardless of your location, you possess the power to make a significant impact on both students and teachers who rely on us daily. Join Leading Educators and become an integral part of driving progress in education. 

Learn About Our Mission & Values:

Mission: Leading Educators partners with school systems to sustain the teaching, leadership, and conditions for every student to succeed in school and in life.

Values:

• Build on strengths: We affirm and begin with the unique and collective talents, experiences, and wisdom of ourselves and others.
• Continuously learn: We develop ourselves and others. We apply new learning and deepened self-awareness to our relationships and practices.
• Prioritize people: We build trust and reflect on the impact of different perspectives and experiences.
• Champion success for all: We re-imagine structures, habits, and mindsets to ensure every learner has access to evidence-based learning opportunities.

Use of Artificial Intelligence in Hiring

• We use artificial intelligence–enabled tools throughout our hiring process, from the moment a candidate applies through the offer stage, to support administrative tasks and the initial review of candidate materials. These tools help us organize, analyze, and surface relevant information efficiently, but they do not make hiring decisions.

• All candidate materials—including applications, resumes, assessments, and interview feedback—are reviewed and evaluated by people. All hiring decisions, including interview selection, advancement, and offers of employment, are made by humans.

• We use AI solely as a support tool to assist with early-stage reviews and process efficiency. We do not use AI in ways that discriminate based on protected characteristics, nor do we use ZIP codes or similar data to target or exclude protected groups. Our hiring practices are designed to be fair, consistent, and aligned with equal employment opportunity standards.

Benefits

• Compensation: 
  
  • If hired for this position, the base salary range is $103,649 to $140,231 per year. Most new hires enter the range at a specific point based on their qualifications and the role level. For this position, the standard starting salary is $121,940, which is based on meeting the minimum requirement of 8 years of relevant experience.
  • If you have more than 8 years of directly relevant experience, your starting salary may be adjusted higher within the range, up to a maximum starting salary of $129,779. This approach ensures that candidates with additional experience beyond the minimum are recognized in the initial salary offer.

• Benefits:
  • 100% paid medical, dental, and vision coverage for individual employees. Additional premium costs are covered 60% by Leading Educators for partners and dependents on medical, dental, and vision plans. 
  • 4% matching 401k plan, Flexible Spending Accounts for medical, childcare and commuter expenses, and an Employee Assistance Program (EAP). Benefits are valued at or above $9,000 for employees.
• Time Off: 
  • First three years of employment, full time staff accrue 22 days a year. 
  • Five additional days are accrued after the third and sixth year of employment.
  • Leading Educators also offer 16 additional paid days off for various holidays, including three floating holidays staff may use at their discretion.

Equal Opportunity Employment 

Leading Educators is an equal opportunity employer.  All qualified applicants will receive consideration for employment without regard to race, color, ethnicity, religion, gender, sexual orientation, national origin, disability, age, marital status, military status, pregnancy, or any other characteristic protected by applicable local, state, or federal laws, rules, or regulations.

Apply: https://leadingeducators.org/careers/opportunities

#LI-CN1