Head of School | Montessori School of Maui

Carney, Sandoe & Associates
July 31, 2023
Job Type
Street Address
2933 Baldwin Ave


Head of School

Montessori School of Maui

Makawao, Hawaii

Start Date: July 2024

Position Overview

Montessori School of Maui (commonly referred to as MOMI), is the largest toddler-through-middle school Montessori School in the state of Hawai`i. The 240 students, faculty, parents, and administrators enjoy a lovely 9-acre campus “Upcountry,” which is not the beach resort area often associated with Maui. MOMIʻs unique indoor-outdoor “living classroom” takes full advantage of its more rural and agricultural environment on the Northwest slopes of the Haleakalā volcano.

Founded in 1978, MOMI is a thriving community in a well-run school. The board is strong, finances are solid, enrollment is stable, and the educational program is firmly grounded in Montessori. Students are well-prepared and successful wherever they matriculate after MOMI. The current Head of School is retiring at the end of the 2023-2024 school year, and MOMI seeks a new leader to build on its many strengths and take it to a bright future.

Maui is a fabulous place to call home; Hawai`i is all about multiculturalism, the weather is terrific (but you already know that!), and the lifestyle is enviable. At the same time, it is an island about a 5-hour flight from North America. Many in the MOMI community are transplants from the continental U.S. who have fallen in love with their home and will never go back. Some people, however, find that despite Maui’s many attractions, they can’t fully adjust to island life. MOMI has been blessed with the stability of low turnover in the Head position and is looking forward to welcoming the next Head (and their family) who are truly looking to take root in this special island community.

About Makawao

MOMI is located in Makawao, a town of about 7,000 residents. Makawao means “Eye of the Forest” and is known as something of a paniolo (cowboy) town, with an annual rodeo that is a big event. At 1,500 feet above sea level, the climate is ideal. There are wonderful restaurants, fun shopping and yet, remarkably, this small town is less than twenty minutes from bustling Kahului with its big box stores and international airport with direct flights to many national and international destinations. You can find more information at: https://mauiguidebook.com/upcountry/makawao-town/

Strengths of the School

Among the many strengths of MOMI, the new Head will find:

  • A warm, welcoming community that embraces the students and each other;
  • A deep commitment to Montessori, which is what truly distinguishes MOMI from other school options in the area;
  • A fabulous, ideal-for-Montessori campus with open spaces, gardens and more;
  • Dedicated faculty, committed to each child in their care;
  • A track record of good preparation and success as students move on to other schools, both private and public;
  • A solid financial foundation built on many years of fiscal discipline, and in particular, it withstood the challenges of the COVID-19 Pandemic;
  • A wise, dedicated and engaged board that understands best practices in Board-Head relationships;
  • MOMI is fully accredited by the Hawai`i Association of Independent Schools as well as WASC, and is a member of the American Montessori Society.

Challenges and Opportunities

  • Faculty recruiting and retention requires ongoing effort.
  • Because Montessori is THE key differentiator for MOMI, there is a desire to further strengthen what is already a solid Montessori educational program.
  • Many would like to see greater emphasis on Hawaiian history and culture in school programming.
  • As all schools made necessary cuts during the pandemic, MOMI is in the process of rebuilding an administrative structure and assuring that faculty and staff have sustainable workloads.
  • There is a desire for enhanced services for students who would benefit from additional learning support.
  • As with many Montessori schools, building the most effective Middle School program is ongoing work at MOMI.
  • While there is a strong program of extra-curricular activities, some in the community would like to see a broader sports program.

Desired Skills and Personal Attributes

  • A passion for and experience with Toddler-Grade 8 student populations;
  • Ability to set a high bar and strive for continued improvement in Montessori education;
  • Eagerness to embrace the unique culture of Hawai`i and a strong commitment to DEI and multiculturalism;
  • A warm, approachable, relational, easy-going, charismatic, empathetic, joyful personal style;
  • Ability to coalesce the school community around a vision of the future and a common sense of purpose;
  • Ability to structure, lead, motivate and support a strong administrative team;
  • A proven track record of successful faculty recruiting, support, evaluation, retention;
  • Financial proficiency sufficient to partner with the Board and the Director of Finance to develop and manage a balanced budget;
  • Experience with both annual and capital fundraising;
  • A desire to make Maui “home” and to embrace and immerse oneself in the local community;
  • A style of collaborative decision-making, but able to make decisions (including occasionally tough ones) when necessary;
  • An excellent communicator who can inspire those within the school community and be the face of the school in the greater Maui community.

To Apply

Interested and qualified candidates are invited to contact the consultants in confidence. Candidates will ultimately need to submit the following materials as separate PDF documents:

  • A cover letter expressing specific interest in the MOMI position;
  • A current résumé;
  • Statement of experience with and philosophy of Montessori education;
  • A list of five professional references with name, relationship, phone number, and email address of each (references will not be contacted without the candidate’s permission) to:

Skip Kotkins

Senior Consultant


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