Choice Schools
  • Other
  • Grosse Pointe, MI, USA
  • Full Time

We are hiring a Headmaster for a new classical charter school opening in 2023!

Be the founding Headmaster of The Hill Pointe School in the Grosse Pointe, MI community.

The mission of The Hill Pointe School is to promote academic excellence grounded in the classics and in our core virtues. We seek to nurture moral citizens and thoughtful leaders.

About the school:

The Hill Pointe School will be a tuition-free public school that will educate students using the virtues-based, rigorous, classical education tradition. Hill Pointe will use a classical curriculum that is time-tested, research-based and is proven to develop children into thoughtful, caring, educated, freethinking young adults. The curriculum emphasizes an education in the humanities, sciences, and arts and integrates Latin language to promote depth in learning.

The school is in receipt of a Letter of Intent from Central Michigan University to serve as the authorizer, and the opening is planned for the 2023-2024 school year. In the first year, the school will open with grades K-5, with plans to add one grade level each subsequent year until it becomes a K-12 program. Hill Pointe will be an independent charter school, is a candidate school with Hillsdale College's K-12 program, and will be part of the Choice Schools Classical Model.

Learn more about Hillsdale College K-12 Education:

About the opportunity:

As the founding school leader, you will be responsible for planning, preparing and implementing all necessary components to successfully launch grades K-5 at The Hill Pointe School. For the first several months of your employment, you will be working closely with the founding board, and the Choice Schools central office team as you plan and prepare to open the school. The headmaster will be responsible for filling open staff positions, recruiting and enrolling students, and establishing the school's standing within the community.

We are looking for someone who has:

  • A broad understanding and deep admiration of the classical liberal arts.
  • A strong desire to achieve outstanding results in the pursuit of excellence for students.
  • A love for building relationships and being on a collaborative team.
  • The ability to develop a team and care for people.
  • An entrepreneurship mindset with the willingness to be a humble change agent.
  • Excellent problem-solving skills.

As the founding Headmaster, you will be responsible for:

  • Leading high-quality instruction and maintaining a thriving school culture.
  • Overseeing, leading and communicating the vision of the school's mission, culture and expectations.
  • Coaching and leading a strong team of teachers and staff.
  • Communicating and cultivating belonging among the students and families.
  • Overseeing the implementation of the Hillsdale K-12 curriculum in alignment with Michigan's Academic Standards.
  • Leading and overseeing staff professional development and training.
  • Overseeing and implementing systems and processes for school operations, including employee relations, enrollment, finance, purchasing, and school improvement, with the support of your superintendent and the robust Central Office Team
  • Developing and implementing invention and enrichment programs to ensure the needs of all students are addressed.

Your professional experience and qualifications:

  • Current Michigan School Administrator certification or enrolled in a program leading to School Administrator certification within six months after the start of employment.
  • The ability to create and execute clear, logical plans by leveraging large systems.
  • The motivation and drive necessary to ensure that instructional-specific conversations are taking place throughout the school through practices intentionally designed to focus conversations and efforts on improving the instruction of every teacher.
  • The ability to motivate others and influence their behaviors around the collective responsibility of educating students.
  • The desire to sustain an effective system of shared leadership and responsibility within the school through relentless follow-up and ownership for results.
  • The ability to develop relationships with staff specifically focused on helping every classroom teacher become a stronger instructional leader and deepening practice.
  • A strong dedication to the success of the whole child and family.
  • The ability to use technology as an instructional tool as a means of analyzing academic achievement data and as a tool to aid effective communication.
  • Excellent verbal and written communication using proper grammar and vocabulary.
  • Successful experience as a teacher and/or school leader.

The job benefits:

  • A collaborative and professional environment.
  • Work-life purpose and fulfillment.
  • Competitive compensation
  • Health, dental, and vision insurance as well as teladoc and flex-spending accounts.
  • 401(K) retirement plan options with up to a 5% match.
  • View our growing list of job benefits here -

The schedule: Full-time, year-round, some travel across the state, and country to visit high performing classical schools.

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Please visit and follow the directions on your screen to apply for this position. Contact Sara Hogle, Director of Human Resources, directly with questions at

The Hill Pointe School will be a K-5* public classical charter school academy located in the Grosse Pointe, MI community. The school is managed by Choice Schools Associates. Choice Schools is a team of educators, literacy specialists, student advocates and many other professions, but first and foremost, we are parents, moms, dads, guardians, grandparents, aunts and uncles who love kids. As a nationally accredited and regionally recognized full-service education service provider, student learning is our organization's mission. We provide a student-focused approach to customized school operations support, including instruction, finance, compliance, communications, human resources, enrollment, curriculum and professional development. Our student-centric philosophy drives us to the path to greatness, allowing everyone - students, staff, teachers, board members and stakeholders to thrive. After more than 20 years of serving diverse models of schools, Choice is committed to being Michigan's most trusted education service provider with the highest-performing schools.

Choice Schools Associates is an Education Service Provider for charter schools in Michigan and is the employer for this position. Please visit for more information. EEOC

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