Fast Facts

The Director of System Strategy at Leading Educators will lead complex educational initiatives aimed at transforming school systems through strategic project management and stakeholder collaboration.

Responsibilities: Oversee targeted projects to enhance coherence in educational systems, manage client relationships, and drive project execution from inception to completion.

Skills: Strong project management, educational leadership, relationship-building across stakeholders, and the ability to translate strategic vision into measurable actions are essential.

Qualifications: A minimum of 8+ years in project leadership or educational leadership with proven experience in K-12 education and client relationships is required.

Location: This is a remote position with moderate travel requirements within the U.S.

Compensation: $103649 - $140231 / Annually

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.

Candidate Application Deadline: 9/14/2025

Position

Imagine a role where your strategic leadership can transform educational systems, where every project you touch has the potential to reshape how schools support teaching and learning. As our Director of System Strategy, you'll be a change agent who bridges innovative thinking with practical implementation.

This position is designed for a dynamic leader who can rapidly learn, adapt, and drive complex projects forward. You'll be responsible for leading targeted, short-term projects that focus on understanding and improving the coherence within state and local school systems. Your work will directly impact how educational organizations develop, implement, and refine their strategic approaches to teaching and learning.

As the primary project lead, you'll be the driving force behind project execution from inception to completion. This means translating complex contract requirements into explicit, progressive actions, coordinating across the Leading Educators team, and managing critical client relationships. You'll work closely with the Senior Director of System Strategy, leveraging your expertise to navigate challenges, explore innovative solutions, and create meaningful change in educational systems.

Do you have expertise in…

• Project management with a track record of designing and executing complex initiatives
• Educational leadership, particularly at the school principal or district level
• Building and managing relationships across multiple stakeholder groups
• Translating strategic vision into concrete, measurable actions

Do you enjoy…

• Navigating ambiguity with creativity and precision
• Collaborating across diverse teams and organizational boundaries
• Continuous learning and professional growth
• Making systemic improvements that have tangible impact on educational outcomes

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 project leadership, client relationship management, or equivalent position
• Proven school Principal or district leadership experience
• Demonstrated strong planning and project management skills, including:
• Designing project plans to support team collaboration
• Meeting client deadlines with precision
• Proven experience collaborating with partners to:
• Build understanding of organizational priorities
• Execute strategic initiatives
• Manage client/partner relationships effectively
• Deep understanding of (or commitment to learning) the K-12 education ecosystem and landscape
• Exceptional comfort with ambiguity and flexibility
• Ability to leverage personal expertise to navigate complex challenges productively
• Proven track record of building trusting relationships across diverse stakeholder groups

Travel Requirements

• This is a remote position requires moderate travel
• 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. 

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.

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Compensation & 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