Seeking Head of School

Kentucky Avenue School is seeking a dynamic and visionary Head of School with strong administrative experience, a passion for teaching, and a demonstrated commitment to progressive community values where every child is able to be themselves and shine.

What is Kentucky Avenue School? Kentucky Avenue School (KAS)  is a small, independent, K-8 progressive school located in Pittsburgh’s Shadyside neighborhood that provides highly differentiated instruction in a warm and inclusive school climate. Our curriculum is responsive, rigorous and socially conscious. Rooted in constructivist philosophy, KAS embraces experiential, project-based, collaborative learning that promotes creativity, self expression, and critical thinking. 

We Value 

  • Respect for self and others 
  • Experiential education 
  • Collaboration and cooperation with faculty, staff, parents, and students 
  • Dedication to the local community 
  • Commitment to diversity and inclusion
  • Honoring the whole child 
  • Active participation within the KAS learning environment 

Enrollment Facts

Enrollment is typically 65-75 students. 

Faculty and Staff

KAS has 18 faculty and staff members. 


The successful candidate will possess the following qualities: 

  • Leads with warmth and empathy
  • Passionate and mission-driven 
  • Culturally competent
  • Promotes collaborative, inclusive learning environments 
  • Strong and effective communicator 
  • Highly organized and able to manage concurrent projects 
  • Ability to stay calm and composed in high stress and challenging situations
  • Self-reflective 
  • Demonstrate the ability to empower and cultivate leadership skills in others 
  • Energetic and ambitious
  • Utilize evidence-based data and resources 
  • Visionary and can create goals to unite a community and foster new connections
  • Curious, lifelong learner 

Essential Responsibilities

The desired candidate will lead and coordinate the administrative and educational activities of the school by executing the following functions either personally or through personnel. They will provide academic leadership for the school and oversee its climate, daily operations, admissions, and budget. They will manage faculty/staff hiring, evaluation, and professional development. They will also guide and support the faculty/staff in curriculum development and maintaining high academic standards. They will seek input from the KAS Board of Trustees, faculty, staff, parents, and students.  The Head of School reports to and is the sole employee of the KAS Board of Trustees. 

Promoting Academic Vision and Strategy 

  • Articulate, advocate, and manifest the school vision consistent with the school’s mission in collaboration with the Board of Trustees. 
  • Ultimately responsible for the overall success of the school providing the school community with educational leadership consistent with the KAS mission, ensuring curriculum goals and programming is implemented. 
  • Enhances faculty development, providing supervision and mentoring of staff and faculty. 
  • Provides leadership for curriculum by assuming overall responsibility and accountability for the planning, development, implementation, and evaluation of curriculum, with the assistance of the academic faculty. 
  • Building of diverse collaborative teams. 
  • Oversees admissions and recruitment and establishes admission criteria and policies. 
  • Ability to build trust and positive working relationships with multiple internal and external stakeholder groups; able to promote high expectations and high quality for all staff.

Organization and Operational Expertise 

  • Lead with experience and confidence in areas of finance, human resources, etc. 
  • Development of systems and policies to ensure progress. 
  • Identify opportunities for growth and innovation. 
  • Ability to analyze and resolve complex issues, while remaining logical and interpersonal.
  • Experience or interest in fundraising and development.

Inspiring Communicator 

  • Inspiring commitment to the KAS mission, to the school, alumni, and greater community 
  • Have the ability to listen actively and speak effectively to parents, students, faculty, and staff.
  • Effective verbal and written communication skills, including effective presentation skills.

Building of Community 

  • Commitment to the strategic imperative of becoming a more inclusive, diverse school community by way of examining policies and practices related to hiring, curriculum, and admissions. 
  • Understand the importance of the local region, and build and foster connections that would benefit the school and greater community.

Minimum Qualifications 

  • Master’s degree or higher from an accredited educational institution in an education-related field. 
  • A minimum of 3-5 years classroom experience teaching in K-8 grade levels.
  • Classroom or administrative experience in a private or independent school setting.
  • PA Professional Instructional Teaching Certification in Elementary Education K-6, or PK-4, or Grade 4-8, or Early Childhood Education, or PA Private Academic Certification in Elementary 1-8
  • A minimum of 3 years of leadership and/or supervisory experience in a school setting.
  • Knowledgeable and experienced in neurodivergent and gifted learning styles and differentiated instruction. 
  • Ability to work independently in a multitasking fast-paced environment employing organizationally sound decision-making. 
  • Strong interpersonal, presentation, and written communication skills facilitating work with all constituencies of the school community. 
  • A passion for innovative, progressive, and profoundly meaningful teaching and learning in a K-8 environment. 

Strongly Preferred Qualifications 

  • Pennsylvania Department of Education-issued certification as an Elementary, or PK-12 Principal Certification or willingness and ability to obtain prior to employment. 
  • Responsive Classroom training 
  • Experienced in STEAM/Maker Movement instruction

Salary and Benefits 

Starting Salary Range $75,000-$90,000. Benefits package includes Medical Insurance, Dental, Vision, 401(k), with KAS Tuition Remission.


Review of applications will begin March 1, 2024, and continue through May 1, 2024, or until the position is filled.

For full consideration, please submit a letter of application, curriculum vitae/resume, an educational philosophy that includes ideal classroom experiences in a K-8 school, three letters of recommendation, official transcripts, and all PA instructional/supervisory certifications. Please send any questions and/or application package electronically Attention to: Search Committee 

Offer of employment is contingent on the candidate satisfactorily obtaining and passing the following prior to commencement of appointment: Pennsylvania Department of Human Services Child Abuse History Clearance, Pennsylvania State Police Criminal Record Check, and FBI Criminal Record Check. Also, as required by Act 168 of 2014, the candidate must satisfy the requirements stated on the Commonwealth of Pennsylvania Department of Education Sexual Misconduct/Abuse Disclosure Release Form.

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