Chief of Learning

City Garden Montessori • St. Louis, MO

77d • $125,000 - $160,000 • Onsite

About The Position

We’re seeking an exceptional instructional leader to ensure every City Garden student experiences the promise of public, equity-centered Montessori education. As Chief of Learning (COL), you will lead through others—guiding our two principals, Director of Curriculum & Instruction, and Director of Special Services—to deliver excellent academic and whole-child outcomes for all 620 of our students.

For more about City Garden, our leadership ethos, and how the COL role fits in, click here.

You are an experienced, equity-driven instructional leader who believes deeply in the potential of every child and every adult. You bring both heart and rigor to your leadership, inspiring trust while holding high expectations.
You are likely described as:
A builder of leaders — You coach, empower, and hold others accountable with clarity and care.
A systems thinker — You translate ambitious vision into sustainable structures that help people do their best work.
An equity champion — You lead with an anti-bias, anti-racism lens and make data-informed decisions to close gaps and expand opportunity.
A whole-child educator — You understand the power of whole-child, constructivist learning and can help others bring it to life in public education.
A reflective learner — You seek feedback, respect the limits of your experience and knowledge, and model growth for your team.
A cultural steward — You have a natural ability to influence peers to uphold a positive culture.
The COL will serve as a strategic, thoughtful leader across the following efforts:
1. Develop and Empower Instructional Leaders
Coach and manage the Principals, Director of Special Services, and Director of Curriculum & Instruction to grow as effective, equity-focused instructional leaders who drive to achieve trajectory-changing outcomes each year.
Build a strong leadership pipeline by identifying and developing emerging leaders across the organization.
Cultivate data fluency and support leaders in using academic, social-emotional, culture and climate data to drive improvement.
Strengthen leadership team culture by combining strong support and clear accountability.
2. Ensure Excellent Teaching and Learning Systems
Oversee implementation of City Garden’s anti-biased, anti-racist Montessori model with consistency and fidelity, with a focus on yielding student outcomes that are among the best in the country.
Partner with instructional leaders to design, implement, and continuously improve curricular, assessment, and intervention systems.
Ensure that student data systems, instructional practices, and support services are aligned to produce equitable outcomes.
Support compliance with all city, state, and federal academic and special education requirements.
3. Foster a Thriving and Inclusive Organizational Culture
Nurture an affirming and connected environment for students, families, and staff across both campuses.
Partner with school leaders to ensure effective student support and behavior systems are in place and staff are equipped to meet students’ learning and behavioral needs with consistency, care, and high expectations.
Build meaningful family partnerships that strengthen belonging, re-enrollment, and student success.
Model transparent, compassionate leadership in moments of change or challenge.
4. Contribute as a Strategic Executive Leader
Serve as a key member of the Executive Team, helping shape City Garden’s strategic direction, priorities, and resource allocation.
Set clear goals for academic, social-emotional, and operational excellence, ensuring alignment with the organization’s mission and strategic plan.
Provide updates to the Board of Directors and partner closely with the Chief Executive Officer, Chief Operating Officer and Chief Advancement Officer on school operations and cross-functional initiatives.
Manage the instructional budget and ensure resources are directed toward the greatest student and staff impact.

Requirements

• Bachelor’s degree required; Master’s degree or higher preferred
• Highly relational people leader with extensive experience managing school teams to achieve strong academic and social-emotional outcomes, particularly with students of color and students living in poverty
• Significant experience directly coaching, managing, and crafting professional development programs for principals and other educators, including evaluation of school principals and other instructional leaders
• Proven instructional leader with a constructivist educational philosophy (Montessori credentials and experience are a plus)
• History of leveraging data to drive strong academic outcomes and close gaps
• Experience with and knowledge of special education policies and best practices
• Understanding of charter schools and, ideally, the St. Louis education landscape
• Experience designing and implementing strong systems and processes in a school setting

Nice To Haves

• Montessori credentials and experience

Responsibilities

• Coach and manage the Principals, Director of Special Services, and Director of Curriculum & Instruction
• Build a strong leadership pipeline by identifying and developing emerging leaders across the organization.
• Cultivate data fluency and support leaders in using academic, social-emotional, culture and climate data to drive improvement.
• Strengthen leadership team culture by combining strong support and clear accountability.
• Oversee implementation of City Garden’s anti-biased, anti-racist Montessori model with consistency and fidelity
• Partner with instructional leaders to design, implement, and continuously improve curricular, assessment, and intervention systems.
• Ensure that student data systems, instructional practices, and support services are aligned to produce equitable outcomes.
• Support compliance with all city, state, and federal academic and special education requirements.
• Nurture an affirming and connected environment for students, families, and staff across both campuses.
• Partner with school leaders to ensure effective student support and behavior systems are in place and staff are equipped to meet students’ learning and behavioral needs with consistency, care, and high expectations.
• Build meaningful family partnerships that strengthen belonging, re-enrollment, and student success.
• Model transparent, compassionate leadership in moments of change or challenge.
• Serve as a key member of the Executive Team, helping shape City Garden’s strategic direction, priorities, and resource allocation.
• Set clear goals for academic, social-emotional, and operational excellence, ensuring alignment with the organization’s mission and strategic plan.
• Provide updates to the Board of Directors and partner closely with the Chief Executive Officer, Chief Operating Officer and Chief Advancement Officer on school operations and cross-functional initiatives.
• Manage the instructional budget and ensure resources are directed toward the greatest student and staff impact.

Benefits

• medical
• dental
• pension (vested after five years)
• school admission preference (as well as discounted preschool and before/after care)
• 21 days annually of Personal Time Off, in addition to holidays and school breaks

What This Job Offers

• Job Type: Full-time
• Career Level: Executive