Head of School – The Colorado Spring School 

Search Process & Timeline:

Opens: Monday, April 27

Closes: Saturday, May 9 at 11:59pm

First Round Virtual Interviews: Tuesday, May 12 and Wednesday, May 13

Final In-person Interview: Friday, May 15 and Saturday, May 16 

• Candidates invited to the final interview should be prepared to be on campus on both days. A schedule will be provided prior to the interview. 

• Final interviews may need to be held the week of May 25. This information will be communicated to the finalists the week of May 12 (if needed). 

Position Summary

The Head of School serves as the chief academic and strategic leader of The Colorado Springs School (CSS), responsible for advancing the school’s experiential educational mission, fostering a strong and vibrant school culture, and leading the academic and community life of the institution.

Working in close partnership with the Chief Business Officer, the Head of School ensures that the school’s academic programs, faculty leadership, enrollment strategy, and community engagement are aligned with the institution’s mission and strategic priorities.

The Head of School focuses on academic leadership, institutional vision, and community engagement while working collaboratively with the Board of Trustees and Chief Business Officer to ensure that institutional goals are supported by responsible financial and operational planning.

Leadership Structure and Reporting

The Head of School reports directly to the Board of Trustees and serves as the primary educational leader of the institution.

The Head of School is expected to work in close partnership with the Chief Business Officer, incorporating financial insight and operational considerations into institutional decision-making

Key Responsibilities

Academic Leadership

The Head of School is responsible for the overall leadership and excellence of the school’s academic programs.

Responsibilities include:

• Setting and advancing the academic vision of the school

• Ensuring the quality and integrity of academic programs across all divisions

• Supporting curriculum development and instructional innovation

• Promoting a culture of experiential-based academic excellence and intellectual curiosity

• Ensuring alignment with accreditation standards and best practices in independent school education

Faculty Leadership and Development

The Head of School provides leadership for faculty recruitment, development, and evaluation.

Responsibilities include:

• Hiring, mentoring, and evaluating faculty and academic leaders

• Supporting professional development and instructional excellence

• Promoting a collaborative and supportive faculty culture

• Ensuring appropriate staffing levels based on enrollment and program needs

• Working to maintain strong academic leadership across the school

School Culture and Community Engagement

The Head of School serves as the primary ambassador for the school and plays a central role in maintaining the strength of the school community.

Responsibilities include:

• Fostering a positive and inclusive school culture

• Engaging actively with students, families, faculty, and alumni

• Representing the school within the broader community

• Supporting school traditions and community-building events

• Strengthening relationships with parents and stakeholders

Enrollment Strategy and Institutional Advancement

The Head of School works closely with the Director of Enrollment to support student recruitment and retention.

Responsibilities include:

• Partnering with enrollment leadership to support recruitment and retention strategies

• Supporting admissions events and community outreach

• Strengthening the school’s reputation and visibility within the community

Development and Fundraising

The Head of School plays an important leadership role in advancing the school’s culture of philanthropy and supporting the financial sustainability of the institution. Working in partnership with the Director of Development and advancement staff, the Head of School helps guide the school’s fundraising strategy and actively participates in development efforts.

Responsibilities include:

• Supporting the planning and execution of the annual fundraising program in collaboration with development staff and the Board of Trustees.

• Engaging directly with current and prospective donors to cultivate relationships and secure philanthropic support for the school.

• Assisting in the solicitation of major gifts that support institutional priorities, including scholarships, program initiatives, and capital improvements.

• Partnering with development leadership and the Board to strengthen relationships with alumni, parents, and community supporters.

• Serving as a visible ambassador for the school, helping communicate the mission, vision, and impact of CSS in ways that inspire philanthropic support.

Through these efforts, the Head of School helps ensure that fundraising and philanthropic engagement support both the immediate needs and long-term sustainability of the Colorado Springs School.

Strategic Leadership

The Head of School works with the Board of Trustees and leadership team to guide the long-term strategic direction of the school.

Responsibilities include:

• Helping shape and implement the school’s strategic plan

• Supporting innovation in programming and student experience

• Identifying opportunities for growth and program development

• Ensuring that strategic initiatives align with the mission and values of the school

Board Partnership

The Head of School serves as the primary liaison between the administration and the Board of Trustees.

Responsibilities include:

• Providing regular reports to the Board on academic programs and school operations

• Supporting Board strategic planning and governance initiatives

• Collaborating with the Board on long-term institutional goals

• Maintaining transparent communication regarding institutional priorities and challenges

Qualifications

Preferred qualifications include:

• Advanced degree in education or related field

• Demonstrated leadership experience in independent schools or similar educational institutions

• Experience managing faculty and academic programs

• Strong communication and community leadership skills

• Experience working with boards of trustees and nonprofit governance structures

• Experience in development and fundraising

Key Attributes

Successful candidates will demonstrate:

• A deep commitment to the mission and values of experiential-based independent school education

• Strong leadership and interpersonal skills

• Strategic thinking and visionary leadership

• Ability to build trust and foster collaboration across the school community

• Commitment to transparency and institutional stewardship

• An ability to support enrollment growth and retention through community engagement and program alignment

• Collaborative leadership style with a demonstrated ability to work effectively with senior operational leaders

• Demonstrated ability to align institutional priorities with financial realities

Impact of the Role

The Head of School plays a central role in ensuring that the Colorado Springs School continues to provide an exceptional educational experience for its students.

Through strong academic leadership and partnership with the Chief Business Officer and Board of Trustees, the Head of School will help guide the school toward a future that is both educationally excellent and financially sustainable.

Salary: $150,000 - $180,000 (with potential for incentive package)

To Apply: Email application materials to [email protected] 

Application materials should include: Resume (with explicit connection to the Key Responsibilities), Cover Letter, and Professional References (minimum of five including current supervisor)