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Head of School

Portland Montessori School
Portland, Oregon
$120,000/year plus benefits
Closing date
Jan 25, 2023

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Focus Areas
Job Function
Education / Teaching, Executive / Senior Management
Position Type
Full Time
Degree Level
Willingness to Travel
up to 25%
Experience Level
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TPMS looks forward to welcoming as its next Head of School an experienced and visionary professional with a proven strategic mindset and strong operational skills who will guide the school into its next phase of growth.

As a dynamic leader, the Head of School will cultivate a collaborative, inclusive, and empathetic work and school culture. A proven effective manager of people, they will develop, lead, and coach a team of highly qualified administrative and educational professionals to deliver on the TPMS mission. Their excellent interpersonal skills will help foster an engaged and supportive family community by inviting participation, listening and responding to feedback, and mediating conflict when necessary. The Head of School’s strong ability to communicate with a variety of constituents will fortify their effective representation of TPMS within the broader community to build partnerships that support the growth of the school. The Head of School will be committed to the principles of equity in support of students, staff, and families, and will co-lead with the Sr. Director of Education the organization’s ongoing Equity, Diversity, and Inclusion (EDI) or Anti-Bias / Anti-Racism (ABAR) training.

As a superior strategic thinker, the Head of School will partner closely with the Board of Directors and leadership team to establish a new strategic direction for TPMS, and create and implement a plan to achieve the School’s short- and long-term goals. They will evaluate current practices and identify new opportunities to ensure the school’s programming, staffing, and funding are aligned to deliver high-quality Montessori education and childcare to a diverse array of Portland families, create a desirable place of employment, and sustain the school’s ongoing growth and financial health.

As an excellent administrator, the Head of School will oversee the school’s successful day-to-day operations, optimize enrollment and retention efforts, and ensure responsible budgeting and financial management. They will be accountable for compliance with local, state, regional requirements, and national educational organizations and accrediting agencies, as a childcare facility, educational organization, and non-profit entity. They will provide regular updates to the Board of Directors, and establish processes for keeping families informed of the school’s activities and developments. In short: the Head of School is responsible for ensuring integrity across the entire operation.

Role in the School

The Head of School / Executive Director is an executive-level position based in Portland, Oregon, and is full-time, salaried, exempt, and year-round.

The Head of School works on campus during regular school hours, overseeing day-to-day operations, supporting faculty and staff, and building meaningful partnerships within the school. They will also attend or host evening meetings when necessary, including the monthly Board meeting, and will host or attend events as needed on occasional weekends.

The Head of School is the spokesperson for the school with all its internal and external constituents including students, parents, faculty, staff, alumni, neighbors, landlord, business community, governmental agencies, as well as local, state, regional, and national educational organizations and accrediting agencies. They will be visibly present, welcoming, and accessible during parent and community events, fostering and facilitating strong bonds across the community.

The Head of School oversees an operational budget of $2.2 million and a staff of 30-35 employees, with direct supervisory responsibility for senior leadership staff. Direct reports include: Sr. Director of Education & Curriculum, Director of Operations, Director of Admissions and Special Projects, Director of Finance, as well as the Operations Coordinator and Development Associate.

The Head of School is the sole employee of the Board of Directors and is responsible for the overall management of the school, in accordance and partnership with the Board’s guidance.

Other information

Preferred start date is July 1, 2023.

The Portland Montessori School is an equal opportunity employer. We are committed to building a diverse and inclusive staff.

This job description is not intended to be a comprehensive list of the duties and responsibilities of the position. The duties and responsibilities of this position may change without advance notice.

TPMS does not currently sponsor applicants or employees for immigration purposes.

This position cannot be performed outside the state of Oregon.

How to Apply

Interested applicants should provide the following:

  • Resume (PDF format) Statement on education and leadership philosophy (500 words) Three professional references (we will not contact without your prior knowledge)

Please submit your application information at our online portal:  All application materials will be reviewed and considered.


Applications will be accepted through January 17, 2023. 

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