Director of Enrollment Management

Kingsley Montessori School•Boston, MA

1d•Onsite

About The Position

Kingsley Montessori School, a Montessori independent school serving students from Toddler through Grade 6 in Boston’s historic Back Bay, seeks a Director of Enrollment Management who is a relationship-driven strategist and systems thinker, capable of clarifying and communicating a nuanced school identity, strengthening family trust, and aligning internal stakeholders, all while building a cohesive, data-informed enrollment and retention program across a multi-division, evolving Montessori rooted 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. The Director of Enrollment Management is a high-impact leadership role at a moment of institutional momentum. Kingsley’s distinctive blend of Montessori foundations and evolving, research-informed practice offers a compelling educational experience, one that requires thoughtful articulation, consistent messaging, and careful stewardship of the family journey. The Director will serve as both architect and ambassador of that experience, ensuring that prospective and current families alike understand, value, and remain deeply connected to the school’s mission. Working in close partnership with the Head of School and senior leadership, the Director will lead all aspects of enrollment management, including admissions, re-enrollment, financial aid strategy, and family engagement. Just as importantly, the Director will help cultivate a shared, school-wide understanding that enrollment is an institutional responsibility, one rooted in relationships, clarity of purpose, and alignment between promise and practice.

Requirements

Demonstrated success in enrollment management, admissions, or a closely related leadership role, preferably in an independent school setting.
Strong understanding of enrollment strategy, including recruitment, retention, and financial aid.
Experience using data and systems to inform decision-making and improve outcomes.
Leadership and Strategic Capacity: Ability to think both big-picture and operationally, translating vision into clear plans, systems, and results.
Skill in managing multiple priorities and leading complex processes with clarity and follow-through.
Capacity to contribute meaningfully to institutional strategy while executing day-to-day responsibilities at a high level.
Experience managing and developing team members, with the ability to build strong, complementary partnerships and foster accountability and growth.
Demonstrated ability to collaborate effectively across departments, particularly with marketing communications, advancement, and auxiliary programs, to align messaging, strengthen outreach, and support broader institutional goals.
Exceptional interpersonal skills, with the ability to build trust across a wide range of constituencies, including parents, faculty, and senior leaders.
Sound judgment in navigating sensitive conversations and complex family dynamics.
Talent for clear, compelling communication, both in person and in writing.
Genuine appreciation for Kingsley’s educational philosophy and its blend of Montessori foundations and evolving practice.
Commitment to fostering an inclusive, welcoming community for a diverse range of families.
Enthusiasm for being a visible, engaged member of school life across campuses and constituencies.

Nice To Haves

Montessori experience is valued but not required.
Familiarity with progressive or student-centered educational models.

Responsibilities

Lead all aspects of enrollment management, including admissions, re-enrollment, financial aid strategy, and family engagement.
Cultivate a shared, school-wide understanding that enrollment is an institutional responsibility.
Strengthen and articulate the relationship-centered enrollment model, ensuring every touchpoint reflects consistency, warmth, and clarity.
Ensure the enrollment process is scalable, sustainable, and well supported by systems and team structure.
Sharpen how the school communicates its identity in the broader market, refining and consistently expressing Kingsley’s value proposition.
Strengthen external messaging, enhance visibility in key markets, and ensure every family interaction reinforces a cohesive and compelling sense of place and purpose.
Build on a culture that values connection, trust, and transparency, ensuring every stage of the family journey from inquiry through enrollment and retention is handled with care, responsiveness, and sound judgment.
Collaborate across divisions to strengthen the overall family experience, identify trends in attrition, and develop proactive strategies to support long-term engagement and satisfaction.
Strengthen partnerships with faculty through transparent communication, structured feedback loops, and meaningful involvement in admissions activities.
Ensure enrollment operations are consistently tracked and proactively executed, with clearly defined calendars, roles, and processes.
Strengthen data integrity, forecasting practices, and enrollment modeling.
Partner closely with academic leaders, student support teams, and faculty to represent the robust systems that support a range of learners.
Align admissions decisions with both the school’s mission and its programmatic capacity, ensuring each enrolled student is well-positioned for success.