Director Of System Strategy

Description:

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)