Head of School: Cimarron School of Living Education (Oklahoma)


Type of Job Full-Time
Job Category Administration
Post Date October 19, 2026

Job Description

Cimarron School of Living Education is seeking a Head of School to lead our community  through an exciting chapter of growth. We are looking for an executive leader who will pair deep  respect for Charlotte Mason’s educational philosophy with sharp operational discipline. In this  role, you will protect and enrich our academic foundation while building the operational,  financial, and enrollment systems needed to ensure long term sustainability.  

The Head of School serves as the chief executive of Cimarron School of Living Education and is  responsible for the overall leadership, health, and advancement of the school. 

Reporting directly to the Board of Directors, the Head of School provides spiritual, strategic,  organizational, and cultural leadership across all aspects of Cimarron. This leader ensures that  the school remains faithful to Christ, committed to its mission, and grounded in the Charlotte  Mason principles that have guided Cimarron since its founding. 

The Head of School leads through a senior leadership team that includes the Director of  Operations, Director of Education, Director of Finance, Director of Inclusion and an anticipated  Director of Development and Admissions. The Head of School is responsible for aligning these  leaders and their teams around a shared vision while maintaining accountability for the school’s  overall performance. 

Cimarron is entering an important stage of its development. The next Head of School will build  upon the strong foundation established by the school’s founder while strengthening operational  excellence, growing enrollment, cultivating a healthy school culture, and stewarding Cimarron  wisely through its next stage of growth. 

Required Qualifications 

The successful candidate will: 

• Demonstrate a mature Christian faith and a life consistent with biblical values. • Affirm and support Cimarron’s statement of faith, mission, and educational  commitments. 

• Be an active member of a local Christian church. 

• Hold a bachelor’s degree from an accredited institution. 

• Have leadership experience in an educational environment. 

• Have experience leading employees, managing complex operations, and building healthy  organizational culture. 

• Have strong financial and organizational judgment. 

• Have experience communicating clearly and effectively with employees, families, Board  members, donors, and community partners. 

• Have a proven track record as a firm, fair and decisive manager with success establishing  clear performance and conduct standards. 

• Have experience constructively addressing performance and behavioral issues. • Successfully complete all required background and reference checks.  

Preferred Qualifications 

Preference will be given to candidates who possess: 

• A master’s degree in education, educational leadership, business, nonprofit leadership, or  a related field. 

• Previous experience as a Head of School, school administrator, or senior private-school  leader.

• Direct experience with Charlotte Mason philosophy and educational practice. • Experience leading a Christian school or faith-based educational organization. • Experience guiding an organization through meaningful growth or change. • Experience with enrollment management, fundraising, donor relations, or school  development. 

• Experience working effectively with a governing board. 

• Essential Leadership Qualities 

 

For the full job description, please visit https://cimarronlivingeducation.com/employment-opportunities/


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