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Regional Manager

Higher Ground Education

Higher Ground Education

Portland, OR, USA
Posted on Thursday, November 16, 2023

Looking for purpose and long-term professional growth? Help change the educational establishment. Develop your skills as a leader in a fast-growth organization.


At Higher Ground Education, we're driven by the desire to bring about widespread change in education today. We believe that the traditional method of education used in most schools is broken. To meet the needs of today's children and to bring about true progress in the world around us, we want to spread an educational model that fosters independence and develops competent, capable, action-oriented critical thinkers.

Our regional management team is the beating heart of our organization. In this role, you’ll fall in love with a basket of schools in a geographic area, and get to know and understand each of them intimately. From the character of each individual classroom, to the most promising, up-and-coming teachers and school leaders who you want to encourage, to the best way to structure staffing and scheduling or build your admissions pipeline, to the unique make-up of each community of families. Working with a tight-knit team of regional specialists, you’ll immerse yourself in all aspects of school operations and community dynamics, in order to lead your schools to stellar program quality and holistic success.

Some of our best leaders have changed careers, and moved into education from other fields. We can teach you Montessori, as well as the ins-and-outs of school operations and managing to profitability. Our excellent training program will take you through every aspect of our schools. What you bring to the table is your talent for leadership and your desire to learn and understand. We need you to see the big picture, while caring about the details. Earn the trust of a team of mission-driven educators, and lead them to greatness.

Our network of Montessori Schools (100 locations and counting with 2,600+ staff) is in hyper-growth mode (40 more new schools this year), and our suite of digital education offerings (ranging from Virtual School to a Learning Management SaaS platform engineered in-house) is scaling up. It’s an entrepreneurial environment for people who enjoy leading in a dynamic environment, and want to dedicate themselves to educational change.

Your Role

As a Regional Manager, you'll be responsible for overseeing a group of Guidepost Montessori (and, in some regions, Academy of Thought and Industry) schools.

  • Proactively quarterback the success of the region. Work with a small team of regional specialists, and manage the school leaders at each individual school, in order to meet our high programatic standards and achieve holistic success at each school.
  • Drive outcomes. You’ll learn to look at the data for your schools, and read and interpret it to tell you whether we are in fact achieving what we set out to achieve. The numbers keep us honest, and allow us to independently check our success. With that in mind, profitability is a core part and expression of our mission. We are unapologetically a for-profit education company and firmly believe that achieving our mission means we are achieving school success.
  • Lean-in when and where your team needs you. Regional Managers are our first point of escalation. Practically, this means that if something goes right, or if something goes wrong, you’ll be pulled in. Supporting our schools through challenging staff situations, thoughtfully navigating relationships with parents, or handling a health and safety incident on campus could all be parts of your week.
  • Lead and build a stellar team. Our Regional Managers are inspiring people leaders. We’re looking for folks that love working with others and aren’t afraid of hard conversations or winning people over. People who thrive in this role get energy from enabling others to achieve their best.

Please note that we believe impact happens on the ground. We’ll want you to be out there in the field and present at your schools. It’s possible to do the role remotely, but in that case it requires 50% travel.

Our Ideal Candidate Will Possess:

It’s ok if you don’t come from an education background, provided that education is important to you, and you feel a connection to our mission. Our current regional management team includes former Montessori teachers who have risen to leadership positions over the course of years and decades, but it also includes young leaders who started their careers as consultants, then fell in love with the mission and purpose our organization represents. If you’re excited by what we’re doing, we encourage you to apply. In general, we’re looking for…

  • Supervisory experience with multi-locations for 3+ years.
  • Proven track record with developing talent and motivating teams.
  • Distinctive communication and writing skills, incl. attention to detail and ability to write persuasively, synthesize information, communicate with empathy.
  • Strong analytical and problem-solving skills, incl. ability to assess a situation by gathering facts and evaluating data (e.g., financial literacy, comfort with basic Excel).
  • Drive to roll-up sleeves and build something, including a propensity to constantly look at people and processes to find ways to make them more efficient, collaborative, and scalable.

Higher Ground Education, Guidepost Montessori, and Academy of Thought and Industry are committed to a policy of Equal Employment Opportunity (EEO). We will not discriminate on the basis of age, sex, race, color, creed, religion, ethnicity, sexual orientation, gender identity, gender expression, national origin, alienage or citizenship, disability, marital status, military or veteran status, or any other legally recognized protected basis under applicable federal, state or local laws, regulations or ordinances. Our leadership is dedicated to ensuring the fulfillment of this policy. When requested, we are committed to reasonably accommodate employees and applicants with disabilities or special needs that may require an accommodation.