Director of System Strategy

Leading Educators Careers

2d • $103,649 - $140,231 • Remote

About The 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.

Requirements

• 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), unless an accommodation has been approved; must be authorized to work for any employer in the United States

Responsibilities

• Lead targeted advisory engagements focused on strengthening instructional coherence and strategic system improvement within district and state partnerships.
• 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.
• 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.
• Guide system leaders in evaluating how technology investments and tools align to instructional goals, leadership capacity, and adult learning priorities.
• Engage in high-level conversations about subject-specific instruction while simultaneously analyzing and advising on the strategic use of technology to advance those goals.
• 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.
• 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.
• Contribute to codifying and improving Leading Educators' system advising practices while advancing real instructional improvement in the districts and states you serve.

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.
• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed