Associate Head Of School Jobs (NOW HIRING)

Fountain Valley School is pleased to partner with DRG to conduct this search. Read the full Opportunity Statement HERE.

Based in an outdoor enthusiast’s paradise, Fountain Valley School (FVS) of Colorado Springs provides educational excellence and one-of-a-kind experiences through its unique location at the meeting point of the Great Plains and the Rocky Mountains.

Set on a historic 1,100-acre campus – the largest privately-owned urban green space in Colorado – with a 40-acre satellite campus in a high mountain valley, FVS is committed to developing leaders who embrace the world with compassion and courage.

The next head of school for FVS will be a dynamic leader who thrives on collaboration with their administration, faculty and board of trustees; eagerly leans into visioning and strategy development as the complex private school environment evolves; thoughtfully curates and confidently communicates the FVS brand and exceptional educational offering to families and supporters of the school; and advances a transformative capital campaign and state-of-the-art facilities expansion under FVS’ strategic plan – the Path to the Summit 2030.

– The Path to the Summit 2030.

Drawing on its Western heritage, Fountain Valley School develops leaders who embrace the world with compassion and courage.

Courage: Embracing intellectual, physical, emotional, and spiritual challenges to stretch beyond perceived boundaries.

Compassion: Caring for others and building an empathetic, supportive global community.

Curiosity: Valuing lifelong intellectual exploration, discovery, and creative effort.

Self-Reliance: Exhibiting personal responsibility, initiative, and accountability.

Open-Mindedness: Recognizing and respecting the deep richness of human experiences.

Reporting to the board of trustees, the head of school serves as the chief executive and educational leader of Fountain Valley School, responsible for the overall vision, health, and success of the institution. The head of school oversees a leadership team spanning academics, community life, enrollment, development, finance, operations, and faculty affairs and is entrusted to work with the leadership team to translate the school's mission and strategic priorities into action from the classroom and dormitories to the boardroom and beyond. The head will guide and inspire the effective leadership team in their respective domains.

The ideal leader will pair deep care for students and community with the strategic and financial acumen to manage a complex, campus-based organization, along with the presence and relational skill to represent Fountain Valley credibly to families, donors, faculty, and the broader Colorado Springs community. This is a transformational moment for Fountain Valley: as the school approaches its Centennial in 2030, the incoming head of school will help carry forward the vision of those who built FVS while setting the course for its second century.

• Partnering with the board of trustees to articulate the school's mission, building consensus and support for the vision across all constituencies
• Leading and executing a capital campaign and broader fundraising strategy, cultivating major donors, alumni, and current parents
• Strengthening enrollment by clarifying FVS's value proposition and building sustainable growth in both the day and boarding populations
• Sharpening and communicating a clear institutional identity
• Overseeing the quality and direction of the school's academic and residential programs and ensuring consistency and thoughtfulness in programmatic decisions
• Attracting, retaining, developing, and evaluating outstanding faculty and staff, with particular attention to stability in key administrative roles
• Managing the school's financial health, including budgeting, the endowment, and oversight of the current capital project and deferred maintenance needs
• Building and maintaining a trusting, collaborative partnership with the board of trustees grounded in transparency and open communication
• Serving as the school's principal ambassador to donors, alumni, prospective families, and the local community
• Engaging with the broader network of independent school leaders to uphold best practices in admission, marketing, faculty recruitment, and fundraising

• Advanced degree preferred; a background in education is beneficial
• Considerable experience leading a complex organization with meaningful oversight of people, programs, and budget
• A demonstrated record in fundraising, advancement, or external relationship-building, with direct experience cultivating major donors and leading or supporting capital campaigns
• Familiarity with boarding school operations and residential life is a plus, including comfort with the rhythms of a campus that includes dorms, athletics, weekend programming, and a 24/7 community
• Experience working with and reporting to a governing board, with the governance fluency to balance appropriate oversight with day-to-day operational authority
• A record of leading an organization successfully through growth, enrollment building, and/or market repositioning
• Experience with budgeting, financial planning, and stewardship of institutional resources, such as an endowment
• Excellent written and verbal communication skills
• Experience navigating organizational transition, with the judgment to build trust and stability within a community
• Familiarity with or genuine affinity for the American West, Colorado, or a similar regional culture and identity is a plus

• An energetic and articulate public-facing leader
• Warm, genuine, and relational; able to build trust quickly across a close-knit community
• An affinity for The West and the unique educational opportunities it offers
• Visible and present, with an authentic enthusiasm for engaging with students, families, faculty, and alumni
• Steady and grounded
• Integrity and transparency in communication and decision-making
• Entrepreneurial and energetic, with a bias toward action
• Humble and collaborative, valuing the ideas and contributions of others
• Resilient and even-tempered
• Genuinely curious and open-minded
• A good listener who seeks to understand before acting

$325,000 – $400,000

The Howe House, our head of school residence, stands out on campus for its beauty throughout, functionality for entertainment, scenic views of the mountains and the prairie, and connection to nature. Like many of our spaces, it displays pieces of our impressive and historical art collection.

FVS believes in supporting the whole person—both professionally and personally. Our benefits include:

• Comprehensive medical, dental, and vision coverage
• School-paid short-term disability, long-term disability, and Colorado paid leave premiums
• School-paid life insurance equal to double the annual salary
• Voluntary life insurance options
• Employee Assistance Program for confidential support services
• Retirement plan with employer contribution
• Full access to our beautiful campus amenities, including pool, gym, walking/jogging loop, workout bikes, scenic hiking and biking trails, and our Mountain Campus

DRG is conducting this search on behalf of Fountain Valley School.

Accepting Applications