Hilltop Montessori School is initiating a search for a Head of School for the 2027-28 school year and beyond. Below is the current Head of School job description; a full Position Statement will be available to candidates in March. In the meantime, interested candidates should send a letter of interest and resume to the Board of Trustees and Head of School Search Committee Chair, Courtney Deal, at [email protected]. 

OVERVIEW: Hilltop Montessori School faculty and staff members understand and promote the school’s mission, vision, objectives, and policies both within and outside the immediate school community. Faculty and staff are expected to attend to each child’s and adult’s individual needs with warmth, guidance, and humor, and to model with their team members the same attributes. 

The Head of School is a collaborative member of the administrative team, and must embrace and be able to speak to Hilltop’s mission as a Montessori school. 

RESPONSIBILITIES

The Head of School will be responsible for implementation of the following:

Education

• Review and approve the annual curriculum for each program.
• Monitor classroom activity to assess compliance with approved curricula, adherence to the Montessori philosophy, and ongoing results/performance.
• Ensure that the curricula and lessons have an eye to diversity, equity, justice, and inclusion. 
• Conduct regular meetings with teachers. 
• Hire and retain quality teachers.
• Conduct annual performance reviews of teachers. Provide staff development opportunities.

Management

• Establish operating policies.
• Ensure that school policies and practices consider the values of diversity, equity, justice, and inclusion. 
• Establish job descriptions (who is responsible for which activities/results). Conduct regular meetings with administrative staff.
• Hire and retain quality staff.
• Conduct annual performance reviews of administrative staff.
• Working with responsible staff and the Grounds Committee, oversee the management of the school’s grounds, including the management and maintenance of buildings and land use.

Finances

• Oversee the work of the Business Office and the Board of Trustees Finance Committee (“Finance Committee”) to coordinate the preparation of the annual budget and organize the presentation of the budget to the Board for review and approval.
• Oversee the work of the Business Office to ensure sound day-to-day financial management practices.
• Coordinate with the Business Office and the Finance Committee to monitor and maintain the long-term fiscal health of the institution.
• Ensure delivery of a cogent financial report to the Board each fiscal quarter. Oversee an equitable and transparent financial aid process to allocate available aid according to school policy.
• Determine staff and faculty compensation, consistent with Board policy and the school budget.
• Ensure that financial policies and practices consider the values of diversity, equity, justice, and inclusion. 

Community

• Encourage and develop a sense of community and involvement by staff, parents and students.
• Attend events that further the building of the school community.
• Represent the school in the larger community, as appropriate (town events, legislative initiatives, educational committees, etc.).

Recruitment and Retention

• Work with the Admissions Director to establish clear goals and broad procedures to recruit students and to build healthy enrollment trends.
• Work with the Administration and teachers to track and support retention of current families.
• Supervise the Admissions Director and staff to seek out and meet with prospective families in order to recruit prospective students.
• Ensure that the school’s admissions and retention policies and practices consider the values of diversity, equity, justice, and inclusion. 

Development

• Coordinate with the Development Director and the Board of Trustees Development Committee to build and incorporate long-term development goals and to create an annual fundraising plan for the school.
• Establish, build, and maintain relationships within the school, with alumni, and with the local community to encourage ongoing financial support of the school.
• Ensure that school’s development policies and practices consider the values of diversity, equity, justice, and inclusion. 

REQUIREMENTS

• BA
• Montessori Credential 
• CPR/First Aid within first three months of employment
• A clear record through fingerprinting
• Strong organizational and leadership skills
• Strong teamwork and a desire to pitch-in whenever and wherever necessary

SALARY & BENEFITS

The salary for this year-round position is $110-140K (commensurate with experience) and benefits include: 

• 50% remission for HMS tuition for one child, others considered within the Indexed Tuition program
• Health care coverage for the employee
• Long-term disability insurance coverage, after the first year of employment
• Retirement with matching employer contribution up to 3% of salary, after the first year of employment
• Professional Development support

Hilltop Montessori School seeks a teacher who can become part of the collaborative Lower Elementary teaching team (for up to 28 LE students) supported by an art teacher, music teacher, PE teacher, learning specialists team, in addition to a collective of staff throughout the school. This position is for the 2026-27 school year and beyond!

 This position will prioritize an individual who:

• Holds values that are aligned with the Montessori framework and principles.
• Is already familiar with equity, anti-bias, and teaching an equitable and culturally affirming pedagogy in the classroom and school system.
• Has experience working with children having a wide range of social, emotional, and behavioral experiences.
• Is a change maker, innovator, excited about working outside the box and bringing their gifts to a community of curious learners.
• Is transparent and comfortable in communication with students, parents, and colleagues.
• Maintains an environment that engages all types of learners and meets students where they are.

Lower Elementary Montessori credential is preferred but not required. 

Compensation is commensurate with experience with a base salary for a Montessori credentialed lead teacher starting at $48,000 and additional compensation for additional degrees, years of experience, and longevity with the school, bringing most teachers well into the $50Ks. The base salary for an assistant is around $34,000, with the same additional compensation opportunities bringing many assistant salaries into the high-$30Ks.

There is also a generous benefits package including: health insurance, matching retirement funds, professional development, short term disability (including maternity leave), tuition remission, etc. We also sponsor assistant teachers for obtaining their Montessori certification!

Hilltop Montessori School seeks a teacher who can become part of the collaborative Upper Elementary teaching team (for up to 28 UE students) supported by an art teacher, music teacher, PE teacher, learning specialists team, in addition to a collective of staff throughout the school. This position is for the 2026-27 school year and beyond!

 This position will prioritize an individual who:

• Holds values that are aligned with the Montessori framework and principles.
• Is already familiar with equity, anti-bias, and teaching an equitable and culturally affirming pedagogy in the classroom and school system.
• Has experience working with children having a wide range of social, emotional, and behavioral experiences.
• Is a change maker, innovator, excited about working outside the box and bringing their gifts to a community of curious learners.
• Is transparent and comfortable in communication with students, parents, and colleagues.
• Maintains an environment that engages all types of learners and meets students where they are.

Upper Elementary Montessori credential is preferred but not required. 

Compensation is commensurate with experience with a base salary for a Montessori credentialed lead teacher starting at $48,000 and additional compensation for additional degrees, years of experience, and longevity with the school, bringing most teachers well into the $50Ks. The base salary for an assistant is around $34,000, with the same additional compensation opportunities bringing many assistant salaries into the high-$30Ks.

There is also a generous benefits package including: health insurance, matching retirement funds, professional development, short term disability (including maternity leave), tuition remission, etc. We also sponsor assistant teachers for obtaining their Montessori certification!

Title: Early Education Classroom Assistant

Responsible to: Children’s House Program Director, Toddler Program Director, Head of School, EEPP Director

OVERVIEW: Hilltop Montessori School faculty and staff members understand and promote the school’s mission, vision, objectives, and policies both within and outside the immediate school community. Faculty, consisting of teachers and assistants, are responsible for providing a Montessori classroom/instructional program that supports the development of the cognitive, emotional, social, physical and spiritual growth of the child in accordance with the school’s mission and vision and the child’s developmental stage. Faculty and staff are expected to attend to each child’s individual needs with warmth, guidance, and humor, and to model with their team members the same attributes. We also ask that teachers have experience with equity, anti-bias, and teaching in an equitable and culturally affirming way and have experience working with children having a wide range of educational, social, emotional, and behavioral needs.

The Early Education Classroom Assistant is an active and contributing member of the Children’s House and Toddler Program Teams, and is responsible for helping to maintain a safe, comfortable, and harmonious Montessori environment, and demonstrates the willingness and flexibility to help out wherever needed within the context of the classroom and the school.  

RESPONSIBILITIES

To assist in establishing a Montessori classroom the Teacher will:

• Become familiar with the Montessori philosophy by attending a Montessori training
• Engage in equitable and culturally affirming teaching practices
• Consistently reflect on own teaching practices to better refine 
• Be a support to classroom teachers and to students, open to flexibility as the daily needs of classrooms can change.
• Record observations in Transparent Classroom, and share with the teaching team 
• Help students maintain their classroom environment as needed
• Provide one-on-one support for students as designated by the Program Director/Learning Specialist
• Supervise lunch, recess, and dismissal 
• Set professional goals with the Head of School
• Help students to develop independence in self-care: toileting, dressing, prepare snack, ensure dishes are washed in the dishwasher daily
• Supervise Extended Day

To ensure a productive relationship with families, the Teacher will:

• Share all information from parents/guardians with the teaching team
• Keep all shared information confidential
• Be professional, positive, and welcoming in all interactions with families

To promote the school community the Teacher will:

• Be familiar with the Student and Family Handbook
• Know and adhere to the expectations in the Personnel Handbook
• Attend all in-service days
• Participate in yearly Montessori professional development
• Grow personally and professionally with anti-bias and anti-racist work to support equity, justice, and inclusion at Hilltop

REQUIREMENTS

• High school diploma or equivalent
• Meet the education requirements for a Northern Lights Career Ladder 1 within first year of employment
• Experience in a preschool environment, and/or a willingness to learn and embrace Montessori pedagogy
• Montessori assistant training within the first year of employment, if appropriate 
• CPR/First Aid within first three months of employment
• A clear record through fingerprinting
• The physical capacity to work with preschool/toddler aged children (includes but is not limited to: bending, minor lifting, working on the floor)

Hilltop is always looking for help with our youngest students! Substitutes may be asked to help cover for planned teacher absences, or last minute coverage. Reach out if you are interested in learning more!

Requirements:

• High school diploma or equivalent
• At least one year experience in a preschool environment, preferably Montessori
• CPR/First Aid
• A clear record through fingerprinting
• The physical capacity to work with pre-school/toddler aged children (includes but is not limited to: bending, minor lifting, working on the floor)

This entry level role is a wonderful “foot in the door” position that has grown many staff people into full-time salaried positions at the school. This position is an hourly position ranging from $17-19/hour depending on experience.