The Croft School: Jamaica Plain - Assistant Head of School

The Croft School – Assistant Head of School (Jamaica Plain)

Start Date: July 2025

About The Croft School 

The Croft School is a young independent school in the Jamaica Plain neighborhood of Boston.  Having opened in Fall 2020, our school currently enrolls 224 students in Preschool through Grade 4.  During the 2025-26 school year, we will expand to include Grade 5.  Over time, we will grow (one grade level per year) into a 300-student Preschool - Grade 6 school. 

We are 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; driven by standardized test outcomes) and private school (elitism; unaffordable; lack of diversity; limited innovation) options.

The Croft School is built around the following core attributes:

• Rigor and Spark
• Student-Centeredness
• Balance
• Strong Relationships
• Outstanding Teachers, Collaborative Improvement
• A Diverse, Inclusive, Anti-Racist Community

Our program includes high-quality math, reading, and writing instruction, innovative project-based learning, age-appropriate opportunities for play and creative expression, frequent enrichment and Spanish courses,  and weekly nature explorations or community trips (field study).  Further, we seek to provide our families with an exceptional experience built around convenience, community, communication, and partnership.

The Croft School has sister schools in Providence (founded 2018) and the South End neighborhood of Boston (founded 2022).

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

About The Role

The Croft School in Jamaica Plain is seeking an exceptional Assistant Head of School.   This individual will be an integral part of the school’s leadership team and overall staff.  In partnership with the Head of School, this individual will be responsible for supporting the growth and innovation of our young school as it expands from its current enrollment and grade span into a full-capacity Preschool - Grade 6 school.  The Assistant Head of School will report to the Head of School.

The Assistant Head of School will work closely with our Head of School, Director of Operations, and teachers to ensure that the student program is executed with excellence and in alignment with the school’s ambitious goals.  As part of this role, this leader will: 

• Manage and coach teachers, ensuring that classrooms embody rigor and spark; 
• Oversee the establishment and maintenance of a positive, joyful school-wide culture that meets the needs of all students; 
• Hold our school accountable to its commitment to student-centeredness, meeting each child’s interests and needs; 
• Oversee student support services, and 
• Communicate regularly and transparently with our school’s families, developing close, trusting relationships with them.

The ideal candidate will be an entrepreneurial team leader who continually seeks out ways in which the school can “raise the bar” and innovate beyond the school’s existing level of high performance.  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 is likely to have had experience as a school leader, leadership team member, or teacher-leader at a high-performing school.

Qualifications and Qualities 

• 2 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 early childhood development; student-centered pedagogy; project-based learning; and the development and oversight of a rigorous, joyous, and welcoming school environment.  

• Experience working with exceptional 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.  

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.

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