Posted: 20-Oct-25
Location: Boston, Massachusetts
Type: Full Time
Salary: 150,000-165,000
Categories:
Overview
Kingsley Montessori School, a Montessori independent school serving students from Toddler through
Grade 6 in Boston’s historic Back Bay, seeks a strategic, mission-aligned educational leader to serve
as its next Assistant Head of School.
Widely regarded as the early childhood and elementary school of choice for families in Boston, Kingsley
offers a uniquely powerful combination of Montessori principles and progressive education within a
close-knit, urban community. With approximately 300 students across two campus buildings on Fairfield
and Exeter Streets, Kingsley delivers a dynamic, child-centered academic experience grounded in
deep respect for each learner’s developmental journey.
Kingsley’s campus includes enchanting, thoughtfully prepared learning spaces and access to nearby
cultural and natural resources, allowing for meaningful experiential learning in the heart of the city.
The school’s programs are rooted in Montessori principles while integrating current best practices in
education, resulting in a dynamic and balanced academic experience. With a mission centered on
preparing students to confidently embrace their future, Kingsley is a place where educators can make
a lasting impact.
Reporting to long-tenured Kingsley leader Tara Hofherr, who will begin her tenure as Head of School
in July 2026, the Assistant Head of School will serve as a key thought partner and operational leader,
advancing the school’s vision and overseeing core elements of its academic program, community life,
and daily operations. The Assistant Head will play a central role in implementing the school’s strategic
plan, which is built upon four foundational pillars: Program, Place, People, and Permanence, with
a particular focus on aligning and integrating Kingsley’s academic experience from toddler through
sixth grade. Direct reports are likely to include the Director of Elementary Education, Director of Early
Childhood Education, and Director of Auxiliary Programs.
Opportunities and Challenges
Lead with clarity, credibility, and vision.
The Assistant Head of School will serve as a strategic partner to the Head of School and a thought leader
within the Administrative Team, playing a key role in implementing and advancing the goals outlined
in Kingsley’s strategic plan and acting as the institutional leader in the Head’s absence. This includes
overseeing day-to-day operations and participating in Board of Trustees meetings and committee work
as requested. The Assistant Head must possess both a wide lens and the ability to execute with
excellence at the ground level.
The Search Group | Carney, Sandoe & Associates page 4
Advance coherence and excellence across programs and campuses.
Kingsley operates across two vibrant campuses, one serving early childhood and the other serving
primarily elementary grades. The Assistant Head will bridge the distance—both literally and figuratively—
between these two learning environments, maintaining a visible presence on both Exeter and Fairfield
Streets. The Assistant Head will work towards an academic arc that is aligned, intentional, and student
centered, while ensuring curricular and developmental continuity from toddler through sixth grade.
Build and sustain a culture of faculty excellence and professional learning.
Working closely with the Early Childhood and Elementary Education Directors, the Assistant Head will
oversee faculty hiring, supervision, evaluation, and professional development. This leader will foster
a faculty culture of reflection, accountability, and joyful inquiry, supporting continuous adult learning
through meaningful feedback, collaboration, and coaching.
Deepen the school’s commitment to community and belonging.
A core pillar of Kingsley’s strategic plan is to ensure that all members of the school community feel
seen, respected, and valued. The Assistant Head will help lead the school’s efforts to integrate DEIB
principles into curriculum, culture, and policies, ensuring alignment with the school’s mission and vision,
and embedding inclusive practices into every facet of school life.
Engage and support families as vital partners in the school community.
Kingsley families are deeply invested in the life of the school. The Assistant Head will collaborate with the
Director of Enrollment Management and Head of School to implement effective admissions, onboarding,
retention, and next schools counseling strategies. The Assistant Head will also work closely with the
Parents Association leadership to support meaningful parent involvement and community engagement.
Qualifications and Personal Attributes
The Assistant Head of School must have a sophisticated understanding of effective teaching and
learning, extensive classroom instructional experience, and the ability to assess progress toward
established outcomes through skilled use of data and key performance indicators. This individual must
also have the flexibility and creativity needed to find alternative ways to reach objectives when barriers
arise and the skills of a resilient negotiator who does not drive themselves or others into a corner.
Finally, as the position works across the school’s two buildings and with numerous partners, excellent
relationship building and collaboration skills will be essential.
To apply and learn more about this role, please follow the link here.