Head of School

Ambleside School of Colorado; Lone Tree (CO); On-site; USD 120,000 - 180,000; Full time

Benefits offered by this job

Health, dental, and retirement plan

Job summary

Ambleside Colorado seeks a Head of School to serve as the senior executive and educational leader of a growing multi-campus organization in Lone Tree/Englewood. This role combines pastoral heart with executive leadership, shaping organizational health, finances, and discipleship while translating vision into execution.

The Head reports to the Board of Directors, who provide governance and strategic direction while entrusting daily operations to the Head of School.

Qualifications

• A mature and deeply personal relationship with Jesus Christ and alignment with Ambleside’s faith commitments.
• Strong resonance with Charlotte Mason’s philosophy and Ambleside Method.
• Ability to articulate Ambleside’s distinctive approach and its value for formation.
• Significant senior leadership experience in a school, church, nonprofit, or mission-driven org.
• Excellent organizational, operational, and financial literacy with budgeting experience.

Responsibilities

• Steward Ambleside Colorado’s Christ-centered mission, Charlotte Mason philosophy, and culture.
• Keep 'for the children’s sake' central in decisions and strategy.
• Ensure consistent Ambleside pedagogy across campuses.
• Strengthen classroom excellence through teacher training and accountability.
• Protect distinctives while fostering humility, growth, and continuous improvement.
• Provide strategic and operational leadership across campuses.
• Build leadership structures and services to enable growth.
• Recruit, develop, and empower leaders with clear accountability.
• Establish measures of academic, financial, enrollment, and health to guide decisions.
• Identify challenges early; empower teams to grow with new campuses.
• Foster a culture of empowerment and autonomous decision-making.
• Oversee financial health and sustainability of the organization and campuses.
• Lead budgeting, forecasting, enrollment planning, staffing, and allocation.
• Partner with the Board to ensure long-term sustainability and stewardship.
• Strengthen enrollment, community visibility, parent engagement, and alumni ties.
• Stay connected to students, families, faculty, and staff as growth occurs.
• Navigate difficult conversations with wisdom, empathy, and conviction.
• Engage major donors to establish and pursue relationships.
• Translate long-term vision into priorities and execution with the Board.
• Provide clear reporting on academics, enrollment, finances, and health.
• Maintain close ties with the Board Chair and surface issues early.
• Lead toward full enrollment, sustainability, and multi-campus growth.
• Position Ambleside Colorado as a flagship within Ambleside Schools International.

Skills

Leadership experience

Emotional intelligence

Relational maturity

Strategic planning

Communication

Stakeholder engagement

Education

Master's degree in education or related field

Job description

Ambleside Colorado is a Christ-centered school community that provides a living education grounded in the philosophy and practical pedagogy of Charlotte Mason. We are committed to forming students who think deeply, love what is good and true, and grow in Christlikeness. Our guiding commitment, “for the children’s sake,” shapes everything we do, as we partner with our deeply relational community in the work of formation and discipleship. With campuses in Lone Tree and Englewood, Ambleside Colorado is entering an important season of growth, with a long-term vision to expand to three to five thriving, fully enrolled campuses, even greater financial sustainability, and becoming a flagship within the broader Ambleside Schools International community.

The Position:

The Head of School serves as the senior executive and educational leader of Ambleside Colorado, overseeing the educational, organizational, financial, cultural, and spiritual health of a growing multi-campus organization. We are seeking a leader who combines the heart of a pastor, the mind of an educator, and the organizational capability of an executive. The Head of School must be someone deeply committed to Christ and personally convinced by the Ambleside model of education, with the relational depth to shepherd a community and the organizational ability to develop leaders, steward resources, measure organizational health, and translate vision into execution.

The Head of School reports to the Board of Directors and serves as a non-voting member, with the Board providing governance, strategic direction, and accountability while entrusting operational leadership to the Head of School.

Responsibilities:

Mission & Educational Excellence

• Steward Ambleside Colorado’s Christ-centered mission, Charlotte Mason philosophy, and culture of deep community
• Keep “for the children’s sake” central to organizational decision-making
• Ensure excellent and consistent implementation of Ambleside pedagogy across campuses
• Strengthen classroom excellence through teacher training, coaching, feedback, and accountability
• Protect Ambleside’s distinctives while cultivating a culture of humility, growth, and continuous improvement

Organizational & Leadership Development

• Provide strategic and operational leadership across Ambleside Colorado’s campuses
• Build the leadership structure, systems, and shared services necessary for future growth
• Recruit, develop, and empower strong leaders, giving meaningful ownership with clear accountability
• Establish meaningful measures of academic, financial, enrollment, and organizational health and use them to inform decisions
• Identify challenges early, empower the right people to solve them, and prepare the organization to grow with additional campuses
• Cultivate a leadership culture of empowerment, equipping other leaders for autonomous, high-impact decision-making

Financial, Enrollment & Community Stewardship

• Oversee the financial health and sustainability of the organization and its individual campuses.
• Lead budgeting, forecasting, enrollment planning, staffing, and resource allocation
• Partner with the Board to strengthen long-term financial sustainability and steward resources wisely
• Strengthen enrollment, community visibility, parent engagement, and alumni relationships
• Remain personally connected to students, families, faculty, and staff as the organization grows
• Navigate difficult conversations with wisdom, empathy, clarity, and conviction
• Engage with major donors to establish and pursue relationships

Board Partnership & Strategic Growth

• Partner with the Board to translate long-term vision into priorities and execution
• Provide clear reporting on academics, enrollment, finances, staffing, and organizational health
• Maintain a close working relationship with the Board Chair and surface significant issues early
• Lead toward full enrollment, financial sustainability, and thoughtful multi-campus growth
• Strengthen Ambleside Colorado’s role as a flagship and resource within the broader Ambleside Schools International community

Qualifications:

• A mature and deeply personal relationship with Jesus Christ and full alignment with Ambleside’s Statement of Faith and the Nicene Creed
• Genuine conviction that the Ambleside approach offers something distinctive and deeply valuable in the formation of children
• Strong resonance with Charlotte Mason’s philosophy and a commitment to becoming deeply formed in the Ambleside Method
• Ability to articulate why Ambleside educates differently and why those differences matter
• Exceptional emotional intelligence, self-awareness, and relational maturity
• A genuine love for students, families, faculty, and staff and a shepherd’s heart for the community
• Ability to listen deeply, build trust, navigate difficult situations, and combine compassion with accountability
• Significant senior leadership experience within a school, church, nonprofit, or similarly complex mission-driven organization
• Strong organizational, operational, and financial literacy, with experience managing meaningful budgets, people, resources, and organizational priorities
• Demonstrated ability to recognize, develop, and empower other leaders rather than becoming the center of decision-making
• Experience leading through growth, complexity, or organizational transition; multi-site or multi-department leadership experience strongly preferred
• Master's degree preferred; degree in education, divinity, organizational leadership, business, or a related field strongly preferred
• Teaching, educational leadership, pastoral leadership, or other significant formation-focused experience strongly preferred

Salary + Benefits

• Benefits: Health, dental, and retirement plan contributions