Director of Old South Preschool

Old South Preschool, located in the heart of Boston’s Back Bay, is searching for a forward-thinking Preschool Director to expand and adapt our well-established and successful program. We are looking for someone who can lead our existing staff of highly qualified teachers to deliver the unique developmental experience we are known for while building on the existing mission by expanding our impact and service to a wider community.

First organized in 1942, Old South Preschool is a non-religious early education program that has been through many iterations. Today, we serve approximately 40 children, ages 2 through 5 in three classrooms, Monday through Friday, 8am to 3pm. Old South Preschool offers an emergent curriculum, play-centered learning, experienced and caring staff, and flexible scheduling at an affordable price. Conveniently situated in Boston’s Copley Square, we take full advantage of our city location, regularly bringing classrooms on outdoor excursions. Families and program staff create a vibrant, interconnected community that holds the development of the whole child as its focus.

We are currently looking for a director who can strategize ways to increase enrollment and adapt our program to better serve the needs of the community — needs that have changed in recent years following the expansion of Boston Public Schools’ pre-K offerings, as well as the coronavirus pandemic. This Preschool Director position represents an exciting opportunity for a creative, passionate educator and an innovative, entrepreneurial administrator who wants to use their skills to reinvigorate our program.

As Preschool Director, your responsibilities will include: 1) supervising, mentoring, and hiring teachers, aides, and interns; 2) developing educational programs in consultation with teachers; 3) overseeing daily activities; 4) communicating and developing relationships with students and their families; 5) ensuring all licensing requirements are fulfilled; and, 5) handling all fiscal duties in coordination with the church’s business office.

For the position, it is necessary that you: 1) meet certification requirements for EEC Director in the Commonwealth of Massachusetts; 2) have relevant teaching and administrative experience; 3) are detail oriented; and, 4) are familiar with all the necessary requirements for operating an early education program in Massachusetts.

While Old South Preschool is not a separate 501(c)3 from Old South Church, its finances and budget function independently. The Preschool Director is, however, part of, and accountable to, the church’s administration; you will report to the church’s Director of Operations and work closely with the business office and finance committee on all financial matters. The preschool’s spaces are shared with the church’s ministries on weekends, which helps to create a mutually supportive environment and relationship between school and church.


Preferred Requirements

  • Bachelor’s or master’s degree in education, child development, or another related field
  • Massachusetts EEC Director I or Director II certification or equivalent (if licensed in another state)
  • Minimum of 3 to 5 years teaching experience in a preschool environment
  • Experience as a school administrator or director, ideally at the preschool level
  • Experience implementing child-led, inquiry-based curricula, with a focus on observation, reflection, and documentation
  • Background in anti-bias curriculum and/or teaching with a focus on celebrating diversity, equity, and inclusion
  • Demonstrated ability to lead, energize, and effectively delegate tasks among interdisciplinary work teams
  • Demonstrated ability to establish and maintain good interpersonal relationships with parents, children, and staff
  • Excellent interpersonal skills, especially written and verbal communication
  • Fluency in social media, and a commitment to developing and promoting Old South Preschool


Essential Functions


  • Oversee and guide the implementation of the school’s emergent curriculum
  • Ensure appropriate staffing and scheduling
  • Hire, manage, and mentor teaching staff
  • Maintain and oversee licensing requirements
  • Recruit families through traditional and innovative means
  • Administer enrollment program
  • Prepare documents for enrollment
  • Communicate with prospective and enrolling families
  • Communications
  • Maintain relationships with families individually and collectively through updates, posting stories/photos on social media, and timely news-sharing
  • Develop and maintain partnerships with wider communities — other preschools, other directors, local businesses, and neighbors, as well as church-wide
  • Be responsible for promoting and advertising the preschool on social media and beyond
  • Fiscal leadership in coordination with the business office
  • Submit payroll to the business office in a timely manner
  • Ensure communication of benefits and paid time off for teaching staff
  • Prepare tuition payments for submission to the business office for deposit
  • Maintain and update accounts for tuition payments, including issuing bills and reminders and following up on missing payments, also in coordination with the business office
  • Develop and administer the preschool budget in consultation with the Director of Operations, business office, and the Old South Church finance committee
  • Share financial reports with responsible parties
  • Maintain and organize physical materials — in classrooms, storage areas, and personal office space
  • Purchase materials and supplies, including food for snack

Specific Skills:

  • Comprehensive knowledge of all EEC licensing requirements
  • Certification in CPR and First Aid
  • Fluency in Microsoft Office and Google Workspace

Job Type: Full-time, with flexibility for summertime hours
Reports to: Director of Operations, Old South Church
Salary: $50,000–$60,000

  • Generous pension
  • Health insurance
  • Dental insurance
  • Paid time off
  • Partial reimbursement for public transit expense


  • Monday through Friday




Instructions to Apply

Please send a cover letter and resume to

Applications are being accepted on a rolling basis, until the position is filled.