About Gill St. Bernard’s School 

Founded in 1900, Gill St. Bernard’s School (GSB) is a PS–12 independent school rooted in the values of courage, integrity, respect, compassion, and excellence. Our 208-acre campus in Gladstone, New Jersey, provides a dynamic environment for students to grow academically, artistically, athletically, and socially. Education at GSB extends beyond the classroom, emphasizing lifelong learning and the development of individual and collective talents. 

Families from Morristown, Summit, Bridgewater, and surrounding communities benefit from collegiate-like facilities, a close-knit community, and a high-touch, relational culture. 

Why Gill St. Bernard’s? Why Now? 

This is a moment of opportunity and forward momentum. With a new Head of School and a clear, forward-looking strategic framework, GSB is poised to strengthen its enrollment strategy, expand its reach, and deepen engagement with families. 

The Director of Enrollment Strategy (DES) will play a critical role in the School’s continued forward movement, serving as a key partner to the Head of School while shaping how GSB attracts, enrolls, and retains students in a competitive marketplace. This role is strategic, visible, and relational, providing senior leadership that unites teams and fosters excellence across the school. 

WHAT WOULD I DO? 

As Director of Enrollment Strategy at GSB, you would lead the design, integration, and advancement of the School’s enrollment efforts, ensuring alignment with mission, market realities, and long-term institutional sustainability. 

You would serve as the School’s chief architect of enrollment strategy, partnering closely with the Head of School and senior leaders to create a coherent, research-informed approach to recruitment, retention, pricing, and positioning across the PS–12 experience. 

This role is both strategic and enterprising, combining vision with hands-on leadership. You would: 

• Set a multi-year enrollment strategy that integrates admissions, financial aid, retention, marketing, and institutional priorities. 

• Translate data, research, and family insights into actionable strategies and recommendations. 

• Ensure enrollment initiatives reflect GSB’s strengths and distinctive value in a competitive and evolving independent school marketplace. 

• Foster a school-wide understanding that enrollment is a shared responsibility, embedded in academic excellence, student experience, and community culture. 

• Partner across academic leadership, student life, advancement, communications, and finance to execute a unified enrollment strategy. 

• Support the Head of School in enrollment forecasting, capacity planning, and market-informed decision-making. 

• Strengthen enrollment systems, processes, and use of data, moving GSB toward proactive, intentional planning. 

This role builds on an existing admissions structure, elevating and integrating practice rather than replacing or destabilizing it. You will lead a team, lead through others, and foster unity and excellence throughout the school. 

Position Summary & Responsibilities 

Reporting to the Head of School and serving on the senior leadership team, the Director of Enrollment Strategy provides strategic leadership for all enrollment efforts, ensuring alignment with GSB’s mission, values, and institutional priorities. 

Strategic Enrollment Leadership 

• Develop and implement a forward-looking, integrated enrollment strategy. 

• Identify and pursue innovative opportunities to enhance family engagement, yield, and net tuition revenue. 

• Partner with senior leadership to set enrollment targets and long-term institutional goals. 

Admissions Partnership & Oversight 

• Work closely with the Admissions Director and team to support operational excellence and family experience. 

• Provide strategic guidance and coaching to ensure mission-aligned, data-informed, market-responsive practices. 

• Encourage innovation and continuous improvement within existing admissions structures. 

Retention & Student Experience 

• Analyze retention and re-enrollment trends to identify opportunities. 

• Collaborate with divisional leaders and student support offices to strengthen the student experience. 

Research, Data & Market Insight 

• Oversee research on internal and external factors influencing enrollment. 

• Translate insights into strategic recommendations for financial aid, pricing, and enrollment initiatives. 

• Share findings with senior leadership and, as appropriate, the Board of Trustees. 

Marketing & Family Engagement 

• Partner with Marketing and Communications to ensure messaging aligns with GSB’s brand and value proposition. 

• Champion a personalized, relationship-centered approach to family engagement. 

• Ensure communications are compelling, consistent, and reflective of GSB’s culture. 

Collaboration, Team Leadership & Presence 

• Maintain an active, visible, and relational presence on campus and in the surrounding communities. 

• Foster collaboration and shared ownership of enrollment across divisions and departments. 

• Support professional growth, clarity of roles, and effective workflows within the enrollment team. 

• Cultivate a culture of innovation, entrepreneurial thinking, and continuous improvement. 

Technology & Process Optimization 

• Evaluate and implement tools and systems to enhance enrollment operations, reporting, and communication. 

• Strengthen processes to improve efficiency while elevating the family experience. 

The Director of Enrollment Strategy will work in close partnership with admissions, marketing, finance, and academic leadership to support excellence in recruitment, retention, and family experience, informed by data, research, and market insight. 

WHO ARE YOU? 

You are a strategic, enterprising enrollment leader with a relational, visible, and collaborative approach. You understand that sustainable enrollment success requires both rigor and imagination. 

You bring: 

• Deep experience in enrollment management or strategy within independent schools or mission-driven organizations. 

• Strong command of data, research, and market analysis, paired with the ability to tell a compelling institutional story. 

• A systems-level perspective connecting enrollment to academics, student life, financial sustainability, and community trust. 

• Confidence at the senior leadership level, offering counsel, asking the hard questions, and helping institutions think beyond short-term cycles. 

You are known for being: 

• Enterprising and innovative, willing to test ideas, refine systems, and challenge assumptions. 

• Collaborative and steady, able to build alignment across divisions, departments, and offices. 

• Thoughtful and measured, especially in moments that require discretion, timing, and trust. 

You lead a team, lead through others, and foster unity and excellence throughout the school. You are comfortable shaping direction and holding the long view. 

WHO ARE WE? 

Gill St. Bernard’s School is a PS–12 independent school grounded in mission, values, and excellence. 

Guided by a clear, forward-looking strategic framework, GSB is strengthening its enrollment strategy, expanding its reach, and deepening engagement with families. 

We believe: 

• Enrollment success builds on the authentic educational quality and distinctive student experience that define Gill St. Bernard’s.  

• Families value clear communication and a cohesive, caring community. 

• Enrollment strategies thrive when grounded in data, research, and relationships, and aligned with institutional vision. 

HOW DO YOU APPLY? 

Gill St. Bernard’s has engaged DovetailED to lead the search for a Director of Enrollment Strategy to start in July 2026.  Interested candidates should review the Opportunity Statement and submit a cover, letter, resume, and list of references as a consolidated PDF to Lynda Hamilton-Kirk, Managing Partner at DovetailED Talent Sourcing at lynda@dovetailedsourcing.com.  Please do not contact the school directly. 

Gill St. Bernard’s School Opportunity Statement Link: htttps://bit.ly/gsbdes. 

Salary:  $140,000 minimum.  Compensation is competitive and commensurate with experience and includes a comprehensive benefits package. 

Gill St. Bernard’s School is committed to building a diverse and inclusive community and is an equal opportunity employer. 

About Gill St. Bernard's School

Gill St. Bernard’s School (GSB) is one of only a handful of New Jersey independent schools to offer preschool through grade 12 on a single campus. Founded in 1900, and home to approximately 600 students, the school is situated on a 208-acre campus with collegiate-like facilities including more than 20 buildings, a performing arts center, a turf field, tennis courts, a working farm, and a two-acre garden and orchard. The campus is conveniently located just north of I-287 and Route 206 in Gladstone, NJ. It is easily accessible from Morristown, Summit, and Bridgewater. The school is a diverse community rooted in the values of courage, integrity, respect, compassion, and excellence, committed to the belief that education takes place not only in the classroom, but on the stage, in the studios, on the fields, and wherever faculty, staff, and students interact. The school firmly believes in lifelong learning and supports the development of individual and collective talents. GSB is committed to recruiting, retaining, and supporting an exceptional faculty and staff of dynamic educators seeking to foster a love of learning, bring out the best in all students, and be guided by the school’s mission with an understanding that a sense of balance permeates all that the school does.

Connections working at Gill St. Bernard's School