Aspiring Head of School Leadership Program

Multiple locations throughout the U.S.

Are you looking for an opportunity to grow, learn, and lead? Do you want to be part of a mission-driven organization  revolutionizing the face of education in the United States and abroad? Join our Aspiring Leaders Program, and lead a school that is transforming lives. 

Who We Are

Guidepost Montessori is a community of trained educators who are driven by a deep desire to bring about widespread change in education today. We believe that the traditional method of education used in most schools is antiquated, outdated, and broken. To meet the needs of today's students and to bring about true progress in the world around us, we need an education model that fosters independence and develops competent, capable, action-oriented thinkers and change agents. To that end, we are committed to dramatically increasing the amount of high-fidelity, authentic Montessori programs, not only in the U.S., but around the globe!

Since our founding 3 years ago, we have opened 20 beautiful schools across the U.S. serving students from birth through high school. We have also launched an innovative, blended-learning training organization to fuel our growth. We're on track to open 20 schools in the next 12 months (including our first international schools!), and plan to open 20+ per year each year after that. 

Come join our Aspiring Leaders program in preparation for a role as Head of School or Assistant Head of School at one of our new Guidepost Montessori schools launching this fall!.

What are we looking for?

In short, we're looking for ambitious, hard-working, self-starters—aspiring leaders with an entrepreneurial state of mind. We value people who have demonstrated the following characteristics in previous roles:

  • Passion/motivation for education
  • High degree of initiative
  • Relentless resourcefulness
  • A strong motivation to achieve results and outcomes
  • Ability to take ownership (an "ask for forgiveness instead of asking for permission" attitude)
  • Confidence in ability to make tough decisions, even with limited information
  • High degree of self-awareness (knowing what you don't know)
  • A growth mindset

What does the program look like?

Our training program runs for approximately 10 weeks, starting in January or June, and will be a mix of seminars, workshops, and actual on-the-job training at our existing schools. You'll have the opportunity to learn from experienced school leaders and entrepreneurs, while collaborating and growing with your peer group. 

Top graduates will have the opportunity to lead their own Guidepost Montessori school this school year at one of our new locations in 2020. We will be opening new schools in the following locations:

  • Denver, CO
  • Orange County, CA
  • Chicago, IL
  • New York, NY
  • Toronto, Canada
  • Vienna, Austria
  • Shanghai, China

At least 3 weeks of the training program will take place in Southern California at our home office. Additional weeks of travel may be required. 

What can you expect as a leader at one of our schools?

  • Ongoing professional development
  • A network of supportive peers and mentors who regularly share best practices
  • Career growth and promotion opportunities
  • A competitive salary
  • Health, dental, and vision insurance
  • Paid time off and paid holidays
  • 100% tuition discount for two children at any school within our network (we serve children 3 months through 12th grade)
  • The opportunity to contribute to a high-quality Montessori program that serves the individual needs of each child

Guidepost Montessori is a project of Higher Ground Education. You can learn more about our mission by visiting

Make a difference. Apply today.

T h a n k   Y o u !

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