Executive Director / School Regional Manager

Chicago, New York, Texas, Washington D.C., or Anywhere with Travel

Are you an experienced Head of School looking for the next step in your career? Do you pride yourself on cultivating flourishing school communities where children, parents, and staff are happy and successful? Are you interested in joining a team of passionate, ambitious educators, striving to change the state of education world-over? If so—we'd love to talk with you! 

Our Mission

Guidepost Montessori is a network of schools supported by Higher Ground Education. We're a community of educators 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 We believe that the traditional method of education used in most schools is antiquated, outdated, and broken.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. 

We believe that the key to international education reform lies in modernizing and mainstreaming the hugely impactful Montessori pedagogy. It is only then that we will succeed in enabling children across the world to realize their human potential as knowledge-guided, value-oriented, efficacious beings, so that they experience, undiluted and unimpeded, the joyous process of growing into successful adults.  

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. 

About the Role 

As a Director of School Success, you'll be responsible for overseeing a group of Guidepost Montessori schools. Guidepost Montessori is a growing community of authentic neighborhood Montessori schools where we strive to serve as a guidepost on the path toward widespread education reform.

You will act as the liaison between central departments and schools, leading new and experienced Heads of Schools to successfully:

  • Meet profitability targets and enrollment goals
  • Achieve our exceptionally high standards for program quality and student learning outcomes
  • Create a supportive, mission-driven campus culture that develops and retains engaged, effective staff
  • Build a tight-knit, supportive, and informed parent community
  • Deliver excellent, highly responsive, and individualized customer service to families
  • Maintain pristine, safe, compliant, and beautiful campus environments
  • Run seamless school operations where school data is always accurate and up-to-date
  • Resolve the toughest student, staff, and parent issues

Essentially, you'll own the outcomes and success of a group of schools! If you have the experience necessary along with an idealistic, entrepreneurial mindset, this is an opportunity to expand your reach and impact by supporting not just one, but many schools that are forming a movement.

Our Ideal Candidate Will Possess:

  • 5+ years experience as a Head of School, Principal or Director at the early childhood and/or elementary level OR 3+ years experience as a regional manager for an educational program
  • Exceptional leadership skills
  • Proven ability to develop and execute strategic plans
  • Excellent oral and written communication skills
  • Experience using data to drive business outcomes
  • Eagerness to roll up your sleeves and dive into the gnarliest challenges
  • Ability to be decisive with limited information
  • Passion for and alignment with our mission

We will prefer you over other candidates if you have

  • AMI or AMS Montessori training
  • Previous classroom teaching experience

thanks for your interest!

we'll be in touch soon.

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