Founding Head of School

The Croft School: Cambridge
Founding Head of School
Cambridge, Massachusetts

Start Date: For the right candidate, our start date is flexible between January 2026 and June 2026, including the opportunity to begin aspects of the role on a part-time basis. The role will be full-time (and year-round) beginning no later than July 2026.

About The Croft School

The Croft School organization is a young, high-quality, independent school organization. We have opened and now operate three growing and acclaimed independent schools in Providence, RI, Jamaica Plain, MA, and the South End neighborhood of Boston, respectively.

We are thrilled by the opportunity to open a fourth school, The Croft School: Cambridge, in September 2026. During the 2026-27 school year, we will enroll students in Preschool and Pre-Kindergarten. During the 2027-28 year, we will expand to include Kindergarten. Over time, we will grow (one grade level per year) into a Preschool-Grade 8 school.

The Croft School is considered by many families and teachers to represent an exciting new type of school that is ideal for those concerned about the area’s existing public school (inconsistent quality; large class sizes; driven by standardized test outcomes) and private school (elitism; non-affordability; limited diversity; lack of innovation) options.

The Croft School: Cambridge will be built around the ethos of rigor, spark, heart, joy, and belonging.

Our early childhood program follows an emergent curriculum that puts students at the center. The program is play- and inquiry-based and includes developmentally appropriate literacy and math instruction. Students engage in frequent enrichment and Spanish courses, as well as weekly nature explorations of community trips (field study). Further, we seek to provide our families with an exceptional experience built around convenience, community, communication, and partnership.

Our elementary program includes high-quality math, reading, and writing instruction, innovative project-based learning, opportunities for play and creative expression, frequent enrichment and Spanish courses, and weekly nature explorations or community trips. In addition to rigorous, relevant, and culturally responsive academics, our Middle School curriculum includes a focus on service-learning and purpose development.

More information about our school can be found here: www.thecroftschool.org.

About The Role

The Head of School (HOS) is responsible for fostering a vibrant and equitable learning environment—one defined by rigor, spark, joy, heart, and a deep sense of belonging. At The Croft School, the HOS prioritizes authentic, trusting relationships with families, students, and colleagues, and places clear, consistent communication at the heart of their leadership. By fostering a culture that views families as essential partners in their children’s education, the HOS ensures a deeply collaborative and supportive school community.

Core aspects of the role include, but are not limited to the following:

Community & Family Engagement: Build strong, trusting relationships with families through individualized and culturally responsive communication.

Visionary Leadership & School Culture: Embody and model Croft’s mission and values in all aspects of leadership and school life.

Instructional Leadership & Academic Excellence: Support teachers in delivering rigorous, differentiated, and engaging instruction that reflects students’ interests, backgrounds, and learning needs.

Talent Management & Development: Provide individualized coaching, feedback, and development to foster professional growth.

Operational & Financial Management: Design and oversee operations and contribute to strategic planning, including the alignment of resources to support school priorities.

The ideal candidate will be an entrepreneurial team leader who continually seeks out ways in which the school can “raise the bar.” Further, given that The Croft School is committed to being a self-reflective, ever-improving anti-racist organization, the right candidate should be excited to contribute to the school’s related efforts and practices.

The candidate most qualified for this role will have experience as a school leader, leadership team member, or teacher-leader at a high-performing school.

Qualifications and Qualities

• 5+ years in a school or teacher-leadership role, including as the school leader, a leadership team member, or as a teacher-leader
• Expertise in early childhood and/or elementary programming, particularly in the domains of student-centered pedagogy; project-based learning; and the development and oversight of a rigorous, joyous, and welcoming school environment.
• Experience working with a wide range of learners.
• Top-tier managerial and coaching skills, sharpened through direct oversight of other teachers and educators
• An entrepreneurial spirit coupled with an ambitious work ethic, as well as a natural desire to go above and beyond to serve students and their families in both expected and unexpected ways.
• Outstanding communication and collaboration skills, inclusive of empathy for others, thoughtful listening, team-orientation, and enthusiasm for being part of a small, close-knit team.
• Self-reflectiveness, humility, and an eagerness to continually improve one’s practice.
• A strong desire to remain in this role for 5+ years.
• A Master’s Degree is preferred. A Bachelor’s Degree and current authorization to work in the United States are required.

Compensation and Benefits

The Croft School offers compensation which is competitive with other local independent and public school opportunities. The compensation for this role will be between $140,000 to $180,000, and will be commensurate with experience.

Non-Discrimination

As an equal opportunity employer, The Croft School does not discriminate on the basis of race, gender, ability, age, religion, sexual orientation, or national or ethnic origin. We encourage applicants of all backgrounds to apply.