Vineyard Montessori School (VMS) is a unique community, made up of inspiring educators and leaders. As an exceptional Montessori school educating children from prek to grade eight, VMS fosters self-motivated, creative, independent thinkers who will develop within themselves the foundational habits, attitudes, skills and ideas which are essential to a lifetime love of learning.

We seek candidates who can contribute to the intellectual, cultural, and racial diversity of our community. We are an equal opportunity employer.

Current Job Openings

Director of School Advancement

Vineyard Montessori School

Part-time Position


  • Create and sustain positive relationships between the school and its constituents, both internal and external, leading them to support Vineyard Montessori School as donors, volunteers, and advocates in fulfillment of our mission.


  • Oversee four major areas of school activity: fundraising, constituency relations (chiefly parents and alumni/ae families), volunteer management, and special events.  The Director of School Advancement must effectively and smoothly integrate these functions with each other and with all other school activities.


  • Work with the Head of School and the Board of Trustees to determine the funding required to meet current and future institutional needs, providing direct support to the Head of School and the Board of Trustees in all fundraising initiatives.


  • Direct all fundraising programs to support school operations and growth, specifically the Annual Fund and an emerging Capital Campaign.  Oversee/manage other fundraising efforts and activities as needed.


  • Oversee a database management system to ensure timely and accurate documentation and reporting of philanthropic gifts, acknowledgement letters, volunteer/donor lists and the like.  Design processes and procedures to allow easy access to and retrieval of constituent data by other staff and volunteers.


  • Cultivate and steward current donors and prospects, creating a climate of future generous giving to VMS.


  • Build a program of ongoing cultivation of foundations, businesses/corporations and other local organizations, increasing awareness of Vineyard Montessori School and its programs, and create a philanthropic climate for additional support of the school.


  • Organize and inspire a strong sense of community and pride in the school on the part of parents, alumni/ae, faculty, staff and other constituent groups through donor recognition events and special celebrations.


  • In collaboration with the Head of School, manage VMS’s development and advancement publications so they support the school’s marketing efforts, as well as meeting the needs of various internal constituencies and informing them effectively about school initiatives including scheduling and organizing events.


  • Serve as the primary point of contact for the Vineyard Montessori School Family Association (VMSFA).  Work with the Head of School to identify and recruit leadership, help coordinate volunteer events, and VMSFA-sponsored events.


Key interfaces:

  • Reports to the Head of School
  • Serves as an active member of the Advancement Committee of the Board of Trustees



  • Three-to-four years successful independent school non-profit/development experience
  • Ability to handle multiple assignments and meet deadlines
  • Ability to work collaboratively and independently
  • Must possess exceptionally strong writing, speaking and interpersonal skills
  • Computer skills essential; familiarity with fundraising software a plus
  • Bachelor’s degree required
Summer Camp Director: Summer 2019

Vineyard Montessori School

Part-time Position



The Director of Vineyard Montessori School Summer Camp supervises a newly designed program and staff for children ages 3 – 6. Located on the beautiful Martha’s Vineyard in Vineyard Haven, MA, Vineyard Montessori School Summer Camp offers a creative, balanced, and dynamic program with a variety of options and activities available. The well-trained and experienced staff includes members of the School’s faculty and others from the local community with years of teaching and/or camp experience.



The new Director will bring experience with young people and energetic, innovative vision to the position. Excellent oral and written communication skills are vital for the Director’s success. A high degree of organization and a demonstrated ability to supervise complex operations, including budgeting, are needed, as is the capacity to professionally represent the School to parents. Bachelor’s degree required. Camp administrative experience is essential, and prior Camp Director experience preferred. Vineyard Montessori School encourages candidates who will add to the racial, cultural, and gender diversity of the institution to apply.



  • Able to commit to 40+ hours a week from June through August 2019
  • Responsible for supervision of all camp administrators and camp staff
  • Assist in interviewing and hiring unit leaders, general counselors, and specialists prior to the opening of camp, including current teachers and college students. Including management and collection of all staff information and forms for employment
  • Management of camp software system
  • Hold pre-camp team meetings
  • Organize and run all promotional events prior to the start of camp and throughout the summer
  • Coordinate parent communication calendar
  • Responsible for compliance with all state licensing
  • Work with the Consultant, Head of School, and Business Office to manage the budget including expenses, income, staff etc.
  • Responsible for all parent communication, tuition collection, camp routines (pick-up, drop-off, extended day), daily schedules, and program operation, including ordering, distribution, and maintenance of supplies and equipment
  • Collaborate with staff on curriculum development prior to opening of camp
  • Create, prepare and conduct all pre-camp staff trainings including weekly staff meetings during the summer
  • Monitor crisis management plan including emergency procedures
  • Direct, supervise, and evaluate all camp operations/programs and staff
  • Regularly monitor safety, compliance with camp policies, and procedures
  • Lead the creation of an atmosphere for developing good morale and well-being among campers and staff
  • Other duties as assigned
  • Salary to be determined based on experience and education


Interested candidates should send cover letter, resume, and list of three references via email with the subject line “Vineyard Montessori School Camp Director” to: headofschool@vineyardmontessori.com, Debbie Jernegan, Head of School

Vineyard Montessori School provides equal employment opportunity to qualified individuals without regard to race, color, creed, gender, sexual orientation, age, national origin, or any other unlawful criteria and to abide by applicable laws and regulations.