The Organization
JH Classical Academy is a Christian Classical Academy, serving students in grades K-12. By utilizing a uniquely challenging and content-rich curriculum, JH Classical Academy works to enrich students’ minds and souls, guiding them towards Christ and into the Great Conversation. With a $5 million budget and 35 full-time employees who each align with the Nicene Creed, Jackson Hole Classical Academy cultivates a love of truth, beauty, and goodness.
The mission of Jackson Hole Classical Academy is to cultivate within its students the wisdom and virtue necessary to discover and fulfill their God-given potential and contribute to a flourishing and free society.
The Opportunity
Jackson Hole Classical Academy is seeking a strategic servant-leader to join its senior leadership team as Associate Headmaster. The ideal candidate will be a mission-aligned educator and team-builder, eager to lead with humility and excellence to build a flourishing academic and student culture.
The Associate Headmaster provides leadership and strategic direction for the school’s academic programs and student life, stewarding the Academy’s classical vision and cultivating a culture of ordered joy.
Strong candidates will bring an extensive and diversified background in private or public classical education settings with at least 5 years of related experience. Additionally, they should possess exceptional instructional leadership skills and a talent for mentoring faculty.
As a vital member of the Academy’s senior leadership, this role supports organizational sustainability and contributes directly to the formation of student-citizens rooted in virtue and capable of renewing culture.
Relocation to the beautiful community of Jackson Hole, WY is required.
ABOUT THE SCHOOL
Founded in 2011, JH Classical Academy was born from a community desire for a school centered on classical education and Christian values.
Classical education, rooted in ancient Greek traditions and evolving through various historical periods, cultivates a pursuit of truth, goodness, and beauty. With the stunning backdrop of Jackson Hole, WY, the JH Academy curriculum addresses fundamental skills in speech, numbers, and art while emphasizing grammar, logic, and rhetoric for critical thinking.
The liberal arts curriculum at JH Classical Academy is challenging and content-rich, focused on the core disciplines of mathematics, literature, history, science, and Latin to help students grapple with the natural order of the universe. Students also work through a structured physical education program to develop the body in concert with the mind and soul. Art education is integral, as chess, music, and visual art provide a refreshing reprieve for the spirit and a reminder of the beauty around them.
WHAT THEY DO
Jackson Hole Classical Academy is a classical Christian school. Graduates of Jackson Hole Classical Academy are not merely well prepared for further studies but are well along the road to becoming citizens capable of transmitting to the next generation the ideas and cultural foundations of Western Civilization.
As a school in the classical liberal arts tradition, the Academy believes that the pursuit of truth always begins with a sense of wonder. Students can love to learn what is true, good, and beautiful through a joyful discovery of the world around them and their own expanding potential.
Academy teachers understand that education is not merely an accumulation of facts or memorization of what others have thought. Educating the heart and mind includes fostering habits of thinking, feeling, judging, choosing, and acting for a complete and virtuous life. Jackson Hole Classical Academy pursues this vision within the historic Christian tradition that calls each person to love God and man.
The mission of Jackson Hole Classical Academy is to cultivate within its students the wisdom and virtue necessary to discover and fulfill their God-given potential and contribute to a flourishing and free society.
The culture, curriculum, and Christian values of the school foster an environment where our teachers and staff can inculcate in students the wisdom and virtue necessary to discover their God-given potential.
The Three Pillars of Success
Classical curriculum
Christ-centered teachers
Focus on student formation
Teachers must love their students and love their subjects, not one more than the other. They must be growing personally and professionally to become more like Christ in their words and actions.
Students must form good habits, with 16 habits divided into age-appropriate groups K-3, 4-6, 7-9, and 10-12, from obedience in kindergarten to integrity in senior year. When those habits are broken, they reflect on what they did, what they could have done differently, and what relationship must be restored.
The classical curriculum is rigorous, teaching to the top of the class and raising the bottom through tutoring and support, and teaches students how to think, not what to think, through a specific canon and a methodology of asking a series of questions and joining what is called The Great Conversation.
POSITION DESCRIPTION
Title: Associate Headmaster
Classification: Exempt
Reports to: The Head of School
Travel: Occasional in-state and national professional development travel
Location: Jackson Hole, WY
Direct Reports: Dean(s) of Students, Director of College Counseling, Athletic Director. Additional academic leadership staff as needed.
EXECUTIVE SUMMARY
The Associate Headmaster reports directly to the Head of School, leads the Office of Academic Affairs, and serves on the senior leadership team, whose work is to ensure the long-term success and sustainability of the school, its faculty and staff, and its mission.
Following guidance and direction from the Head of School, the Associate Headmaster provides leadership, strategic direction, continuous improvement, and alignment of the school’s academic programs, academic operations, and programs relating to student culture. This individual ensures that the school’s curriculum, instruction, student life, and faculty development reflect the Academy’s mission to cultivate wisdom and virtue through classical, Christ-centered education.
The Associate Headmaster serves as a strategic thought partner to the Head of School and works collaboratively to shape and strengthen the Academy’s academic vision, faculty excellence, and student culture.
DUTIES & RESPONSIBILITIES
Academic Leadership
Manages high-functioning academic team and drives continual improvement of the team through a goal-oriented framework. Coordinates team meetings to ensure consistency in application of best practices, and operates within budget.
Assists Head of School in the hiring, academic onboarding, and evaluation of faculty.
Provides instructional coaching leadership for faculty as a constitutive member of the school’s instructional coaching team.
Works with Head of School to design and implement professional development programs, teacher in-service days, and faculty meetings, to support faculty in their vocation.
Conducts crucial conversations, as needed.
Academic Programming and Operations
Prepares and manages the school’s academic operating budget.
Works with Head of School to prepare academic calendar and class schedule and advises Registrar and Director of Campus Operations on scheduling matters.
Liaises with parents and supports the mission, vision, policies, and procedures of the school; assists Director of Admissions with campus tours.
Manages faculty duty assignments and academic stipends.
Serves as a member of the academy’s Emergency Response Team.
Annually reviews the family and faculty handbooks and proposes revisions to the Head of School.
Ensures alignment of academic programs with classical curriculum and pedagogy and regularly reviews teacher gradebooks, lesson plans, and curriculum to ensure quality academic programs.
Runs the school’s summer academic programs.
Oversees the Director of College Counseling to ensure cultural alignment between the school’s career and college counseling programs and its academic mission.
Student Culture and Life
Designs the programming of school events and activities to support and safeguard a student culture of ordered joy; works with the Events Manager to ensure the proper planning of cultural events.
Manages Dean(s) of Students to cultivate and safeguard a culture of ordered joy and maintain standards of student behavior.
Oversees the Athletic Director to ensure cultural alignment between the school’s athletic programs and its academic mission.
Senior Leadership
Upholds and affirms the school’s mission in private and serves as ambassador for the school’s mission in public.
As a member of the senior leadership team, provides leadership to ensure the long-term organizational health and sustainability of the academy, its faculty and staff, and its mission.
Provides information to the Board, Board Committees, and other entities as requested.
Completes annual evaluation of direct reports and makes recommendations to the Head of School on hiring decisions in the academic vertical.
Performs other duties and projects as assigned by Head of School.
MISSION ALIGNMENT
Jackson Hole Classical Academy operates in the historic Christian tradition. All faculty, staff, and board members annually reaffirm their commitment to the Nicene Creed. During the initial screening process, applicants are asked to affirm their agreement with the Nicene Creed, before continuing in the application process.
CHARACTER
Integrity
Sound Judgment
Reliability
Confidentiality
Mature Christian faith (Must be able to sign the Staff Faith Commitment)
Servant Leader
COMPETENCE
Classical Pedagogy and Educational Philosophy
Academic Leadership
Instructional Coaching and Curriculum Oversight
Faculty Development and Team Management
Emotional Intelligence and Conflict Resolution
Operational Planning and Budgeting
Proficiency with MS Office Suite, Google applications and relevant school management systems
CHEMISTRY WITH THE CULTURE
Energetic and highly relational
Passionate about classical Christian education
Life-long learner and teacher at heart
A winsome statesman for virtue and wisdom
COMPENSATION PACKAGE
Salary is commensurate with experience and will be discussed in a personal interview. Full-time benefits, including healthcare, cost-of-living adjustment, and IRA matching, are available.
OPPORTUNITIES & CHALLENGES
Opportunities
Beautifully situated in Jackson Hole, Wyoming, JH Classical Academy is a perfect place for outdoor activities and educational experiences. Alongside the natural beauty, the Academy provides a cost-of-living adjustment for employees, which makes living in Jackson more tenable. These elements make JH Classical Academy an ideal environment for attracting exceptional educators from around the country.
JH Classical Academy is blessed with a committed leadership team, faithful families, and a culture that values intellectual rigor, spiritual formation, and joy in learning. For a leader passionate about classical education, this is a rich environment in which to mentor faculty, shape student life, and build enduring academic programs rooted in virtue and wisdom.
The JHCA Foundation has procured 40 acres of prime real estate and has begun construction on a $100M+ state-of-the-art educational facility at the base of the Grand Tetons. The new campus is scheduled to open in Fall 2025 and will offer a beautiful and inspiring space to teach and form young minds. With this new space, the school is poised to become a national model for a missional Christian approach to classical education. The new Associate Headmaster will have the exciting opportunity to shape how this new environment supports and enhances the school’s academic and cultural mission from the ground up.
Challenges
With a strong founding vision and passionate community, recent leadership transitions have created the need to reinvigorate the curriculum, culture, and academic programs to ensure that they fully reflect the best practices of classical Christian education. The Associate Headmaster will help lead this effort, providing consistency, vision, and academic excellence across grade levels and subject areas.
In partnership with the Head of School, the Associate Headmaster will play a vital role in building new academic systems and structures that deepen student engagement and ownership and that enrich the overall academic and cultural experience. This work will include implementing clear processes, strengthening instructional practices, and cultivating a joyful, orderly culture of learning across the school.
JACKSON HOLE, WYOMING
Nestled in the heart of the Teton Range, Jackson Hole embodies a unique blend of rugged wilderness and vibrant community life. Renowned for its stunning natural beauty, Jackson Hole offers outdoor activities year-round.
During the winter months, the area is a haven for skiing and snowboarding enthusiasts, with Jackson Hole Mountain Resort and nearby Grand Targhee Resort providing world-class slopes and breathtaking vistas. The annual Jackson Hole Rendezvous Festival draws music lovers and outdoor adventurers alike, showcasing both local talent and internationally acclaimed artists against the backdrop of the majestic Tetons.
In the summer, Jackson Hole is a playground for hikers, bikers, and wildlife enthusiasts. Grand Teton National Park and nearby Yellowstone National Park offer endless space to explore, from scenic drives and wildlife viewing to challenging hikes and serene lakeside picnics. The Snake River weaves through the valley, providing thrilling whitewater rafting adventures and tranquil float trips.
The town of Jackson exudes a quaint charm with its wooden boardwalks, art galleries, and Western-inspired architecture. The Town Square, adorned with elk antler arches, is a hub of activity where locals and visitors gather for events like the weekly Jackson Hole Farmers Market or the annual Jackson Hole Rodeo.
Jackson Hole's real estate market is known for its high prices relative to national averages, reflecting its appeal as a vacation destination for outdoor enthusiasts. The average price for a 3-bedroom house in Jackson Hole, Wyoming typically ranges from $1.5–3 million. JH Academy offers a cost-of-living adjustment to support employees living in the area.
If, after prayerfully reviewing this information, you believe this role fits you well, or if you know someone you would like to recommend, please contact:
Dr. Rich Kidd
Managing Partner
mobile :: (757) 642–0622
email :: rich@missionleadership.org
Daniel Tubbs, M. Ed.
Search Consultant
mobile :: (757) 452-1001
email :: daniel@missionleadership.org