Educators Collaborative is pleased to be assisting Near North Montessori School (NNM) in its search for a Director of Enrollment Management. This is a senior leadership role at a pivotal moment for the school, offering the opportunity to strengthen enrollment strategy, sharpen market positioning, and ensure long-term enrollment health in close partnership with the Head of School and senior leadership team. 

Shaping the Next Chapter of Enrollment at Near North Montessori 

Near North Montessori seeks an experienced, thoughtful, and data-informed enrollment leader to serve as its next Director of Enrollment Management. This is a compelling opportunity for an admissions professional who understands enrollment not only as recruitment and admissions, but as mission stewardship, community building, and institutional strategy. 

The successful candidate will bring the ability to balance relational excellence with analytical rigor—leading with warmth and clarity while grounding decisions in data, trends, and long-term planning. As the school continues to stabilize following leadership transitions and looks ahead to its next phase of growth, the Director of Enrollment Management will play a central role in shaping who joins—and remains part of—the Near North Montessori community. 

This role requires a leader with the presence and judgment to serve as the school’s enrollment expert: someone who can guide strategy, set expectations, collaborate across departments, and help the community understand how enrollment decisions advance the school's mission, financial sustainability, and diversity goals. 

Near North Montessori: A Community Rooted in Mission and Momentum 

Founded in 1963, Near North Montessori is one of the nation’s largest and most respected Montessori schools, serving more than 550 students from infancy through Grade 8. Deeply rooted in the Montessori philosophy and a commitment to whole-child development, the school is known for its inclusive community, academic rigor, and strong sense of purpose. 

Near North Montessori’s identity is shaped by its long-standing commitment to independence, curiosity, and responsibility, as well as by the deep engagement of its families, faculty, and staff. The school functions both as a citywide educational destination and as a close-knit community, united by shared values and a belief in the transformative power of Montessori education. 

Following leadership transitions in recent years, the school is entering a period of renewed stability and optimism. With a permanent Head of School in place and a Board committed to strengthening systems, leadership, and trust, Near North Montessori is well-positioned to evolve its enrollment work in ways that are more strategic, transparent, and sustainable. 

Mission 

Near North Montessori’s mission is to guide the development of each child to reach their fullest potential—academically, socially, emotionally, and ethically—by providing an authentic Montessori education rooted in independence, curiosity, and responsibility. 

Beliefs and Community Attributes 

• Our Students are active participants in their learning, developing independence, empathy, and critical thinking from the earliest years. They thrive in an environment that nurtures self-direction and creativity and are encouraged to make meaningful contributions to their classrooms, their communities, and the world around them. 
• Our Guides (Teachers) are highly trained Montessori educators who embrace the dual role of facilitator and mentor. Deeply committed to child development, they create respectful and responsive environments where students are empowered to explore, inquire, and grow. Our guides pursue ongoing professional development to remain at the forefront of Montessori practice and whole-child education. 
• Our Parents and Families are essential partners in the educational journey. They are active members of a vibrant, engaged school community and support NNM’s mission by reinforcing its values at home and contributing their time, talents, and insights to enrich the life of the school. 
• Our Learning Environment combines rigorous academic standards with intentional social and emotional development. In carefully prepared classrooms and dynamic co-curricular programs, students develop confidence, collaboration, and a lifelong love of learning. 
• Our Preparation for the Future begins with cultivating curiosity and agency. Students emerge from NNM with the ability to think critically, act with compassion, and advocate for themselves and others—ready to contribute meaningfully in high school, college, and beyond. 
• Our Community is inclusive, intentional, and deeply rooted in a shared commitment to Montessori values. We embrace diversity of thought, background, and experience, and we believe that every child has the right—and the ability—to learn, grow, and belong. We are guided by the principles of equity, justice, and peace, and strive to model those ideals in our daily actions and decisions. 

Grounded in this mission and these shared beliefs, Near North Montessori draws strength from a community that is deeply invested in the school’s success and future. These institutional strengths form the foundation upon which the school is building its next phase of enrollment stability and growth. 

The Campus and Surrounding Area 

Near North Montessori has invested significantly in its physical environment to support experiential learning, creativity, and community engagement. The school’s purpose-built campus includes: 

• A rooftop urban farm used for science and sustainability education
• A newly renovated gymnasium supporting physical education and schoolwide events 
• A dedicated Innovation and Design Lab for STEM exploration and hands-on learning
• A reimagined outdoor playground currently under development 
• Light-filled classrooms designed to foster independence and collaboration 
• A Montessori-curated library and music room 
• Flexible spaces for community meetings and performances 

The campus is located in Chicago’s Wicker Park neighborhood, approximately two miles from downtown. The area is known for its mix of historic character and modern energy, with a diverse blend of families, artists, entrepreneurs, and local businesses. Restaurants, cafés, art galleries, and shops are within walking distance of the school. 

Near North Montessori is well-connected to public transportation. The CTA Blue Line (Division stop) is a short walk away, offering direct access to downtown Chicago and O’Hare International Airport. Several major bus lines serve the area, and the Metra Clybourn Station—providing access to Chicago’s northern suburbs—is less than ten minutes away by car or bike. 

Nearby green spaces, including Eckhart Park and the 606 Trail, offer opportunities for outdoor play, athletics, and community events. Cultural institutions such as the Museum of Contemporary Art, Lincoln Park Zoo, and Navy Pier are easily accessible, reinforcing Near North Montessori’s commitment to connecting learning with the wider world. 

This urban setting enhances the school’s strong sense of community. Many students walk or bike to school, and faculty often live nearby—reinforcing Near North Montessori’s role as both a beloved educational institution and an integral part of the Wicker Park neighborhood. 

Enrollment Context and Opportunity 

Near North Montessori benefits from strong yield, high retention, and a deeply engaged school community. Even amid a decline in application volume over recent years—particularly at the youngest entry points—overall enrollment has remained steady, reflecting mission alignment and family loyalty. 

The recently completed Enrollment Management Audit and Recommendations offered a candid assessment of current challenges and opportunities, identifying application volume as the most pressing concern while affirming the school’s many strengths. The audit also outlined a clear, mission-aligned path forward, emphasizing the need for sharper messaging, more strategic use of data, and a multi-year enrollment plan. 

Key opportunities include: 

• Increasing application volume, especially in early childhood entry points
• Clarifying and simplifying enrollment messaging 
• Using data more strategically to inform recruitment, retention, and financial aid decisions 
•  Strengthening faculty and staff engagement in enrollment and retention
• Aligning enrollment strategy with long-term financial sustainability

The Opportunity Ahead 

The Director of Enrollment Management will join Near North Montessori at an important inflection point. With strong yield and retention as a foundation, the school is ready to focus on expanding its applicant pool, refining its market presence, and using enrollment data as a strategic tool across the institution. 

The next Director will be responsible for implementing the Enrollment Audit’s recommendations while strengthening systems, processes, and collaboration across departments. This is an opportunity to lead enrollment as an enterprise function, closely aligned with mission, finance, and advancement. 

Strengths of the School

Near North Montessori (NNM) benefits from a number of strengths that position the school well for long-term enrollment stability and growth. The school is consistently described by families, faculty, and staff as a place of belonging, shared purpose, and deep commitment to children—an essential foundation for effective recruitment and retention. 

Several strengths support Near North’s enrollment work at this moment:  

Strong retention and yield. Near North maintains high retention and yield rates relative to peer schools, reflecting strong mission alignment, family satisfaction, and confidence in the educational program.

A compelling Montessori value proposition. Families choose Near North Montessori intentionally for its authentic Montessori practice, whole-child approach, commitment to equity and diversity, and vibrant urban setting. These elements continue to resonate strongly with enrolled families and represent important assets for recruitment messaging. 

Engaged families and faculty. The school community is deeply invested in student success and school life. Faculty and staff are strong ambassadors for the school, and families often cite relationships and community as primary reasons for enrollment and retention. 

Clarity about enrollment challenges and opportunities. The Enrollment Management Audit provides a candid, data-informed assessment of current enrollment dynamics, identifying application volume—particularly at early entry points—as the most pressing challenge. This shared understanding creates alignment and readiness for focused, strategic enrollment leadership. 

Opportunity to strengthen systems and strategy. With intentional focus on messaging, data use, and multi-year planning, Near North Montessori is well-positioned to translate strong fundamentals into sustained enrollment health and long-term institutional stability. 

Taken together, these strengths reflect a school that is not starting from scratch, but rather one that is ready to move from strong outcomes to a more deliberate, proactive enrollment strategy. The next Director of Enrollment Management will have the opportunity to build on these assets and help shape a durable, mission-aligned enrollment program. 

Leadership Responsibilities and Opportunities 

Reporting to the Head of School and serving on the senior leadership team, the Director of Enrollment Management will be responsible for: 

Strategic Enrollment Leadership 

• Develop and execute short- and long-term enrollment and retention strategies aligned with mission and institutional goals 
• Lead a multi-year enrollment plan grounded in data, trends, and capacity 
• Set enrollment goals that support economic, racial, and ethnic diversity

Recruitment, Admissions, and Retention 

• Oversee recruitment, admissions, re-enrollment, and retention from inquiry through enrollment 
• Lead tours, yield activities, and family engagement 
• Partner with academic leadership on applicant assessment and admission decisions 

Data, Analysis, and Systems

• Maintain and analyze enrollment, retention, and financial aid data 
• Use tools such as DASL, EMA, and internal dashboards to inform decision-making 
• Support budget development through enrollment projections and modeling 

Collaboration and Community Engagement 

• Partner with Advancement on messaging, publications, and digital presence 
• Engage faculty and staff as partners in enrollment and retention 
• Support families through the financial aid process 

Team Leadership and Operations 

• Supervise the Registrar and manage admissions operations 
• Ensure enrollment practices reflect best practice, equity, and transparency 

Skills, Experience, and Leadership Attributes 

• Bachelor’s degree required 
• Prior admissions or independent school leadership experience 
• Montessori experience or demonstrated understanding preferred 
• Strong communication, relational, and organizational skills 
• Comfort with data, CRM systems, and enrollment technologies 
• Inclusive, collaborative leadership style grounded in DEI principles 

Above all, the successful candidate will be energized by Near North Montessori’s mission and motivated to help build a thriving, diverse, and sustainable school community. 

A complete, detailed job description is available to candidates upon their application for this position. 

How to Apply 

Applications will be reviewed as they are received. Candidates interested in this position are asked to submit the following materials in a single merged PDF document, in the order listed:   

• EC Candidate Summary Sheet (you’ll be asked to make a copy upon opening) 
• Letter of interest, addressed to the Head of School  
• Current résumé   
• A list of five or more references with contact information (including phone numbers and email addresses)   
• Disclosure Form (you’ll be asked to make a copy upon opening) 

Please send applications and address inquiries to:   

George Sanderson, Partner, Educators Collaborative, gsanderson@educatorscollaborative.com 

Carol Santos, Partner, Educators Collaborative, csantos@educatorscollaborative.com  

About Near North Montessori

Over 60 years old, NNM serves 556 students from toddlers to 8th Grade along with 140 employees. Located near Wicker Park in Chicago, NNM is one of the largest Montessori schools in the nation. Highly regarded for its Montessori pedagogy and innovation, NNM hosts a rooftop garden, an innovation studio, a swimming pool, a playground, a rooftop urban farm, and a Sandwich Shoppe which is managed by students. Learn more about us on our website: www.nnms.org

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