Educators Collaborative is pleased to be assisting Near North Montessori School (NNM) in its search for a Director of Institutional Advancement. This is a senior leadership role at a pivotal moment for the school, offering an opportunity to strengthen advancement strategy, build trust, and advance Near North Montessori’s long-term sustainability in close partnership with the Head of School and Board of Directors.

A Strategic Moment for Advancement Leadership

Near North Montessori seeks an experienced, relational, and strategic advancement leader to serve as its next Director of Institutional Advancement. This is a compelling opportunity for a fundraising professional who understands advancement not only as revenue generation, but as mission stewardship, relationship-building, and enterprise leadership.

The successful candidate will bring the ability to lead with clarity and empathy, build strong systems and teams, and serve as a trusted thought partner to the Head of School and Board. As the school continues to strengthen leadership, operations, and community trust, the Director of Institutional Advancement will play a central role in shaping the next chapter of Near North Montessori’s story—ensuring that philanthropy supports access, excellence, and long-term sustainability.

This role requires a leader with the presence and judgment to confidently steward sophisticated donors, cultivate a high-performing Advancement team, and maintain clear, disciplined boundaries around governance, decision-making, and advancement best practices. The Head of School is seeking a Director who brings credibility, calm authority, and the ability to lead advancement work as the expert—someone who can guide strategy, set expectations, and hold the line on what effective, ethical fundraising requires.

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 highly-regarded Head of School in place and a Board committed to strengthening systems, leadership, and trust, Near North Montessori is well-positioned to evolve its advancement 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 growth and sustainability.

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.

Advancement and Financial Context

Near North Montessori currently raises just over $1 million annually through its Annual Fund and key fundraising events. While philanthropic results are trending upward, school leadership and the Board recognize that, based on institutional capacity, community engagement, and peer benchmarks, Near North should aim to raise $1.5–$2 million annually over time.

A $2.1 million capital campaign is currently in its final stages and should be completed by the time the new Director of Institutional Advancement is appointed. There are no plans for additional capital campaigns currently in place.

The school maintains a Board-designated fund of approximately $7.5 million and has a healthy overall financial foundation. Advancement efforts are supported by a small professional team, with some annual fund work currently supplemented by consulting support. A priority for the next Director of Institutional Advancement will be to strengthen internal capacity, reduce reliance on consultants, and build a stable, data-informed advancement operation.

The school’s Advancement Strategic Plan has been drafted, and as the new Director arrives, it will serve as a foundational roadmap for the role.

It is within this context that Near North Montessori seeks its next Director of Institutional Advancement, a leader prepared to translate community goodwill and institutional momentum into sustained philanthropic impact.

The Opportunity Ahead

The Director of Institutional Advancement will join Near North Montessori at an important inflection point. While the school has a strong tradition of giving and an engaged parent community, recent years of transition have affected donor confidence, consistency, and systems. The next Director will be responsible for bringing the Advancement Strategic Plan to life while also strengthening the operational foundation necessary for long-term success.

Key priorities include:

• Cultivating a strong and dynamic advancement team
• Building and deepening relationships with families and donors
• Strengthening Near North’s case for support, centered on students and mission
• Achieving annual philanthropic goals with greater consistency
• Improving donor retention, participation, and stewardship
• Building and utilizing best-in-class data-driven advancement systems and practices
• Strengthening integration between Advancement, Finance, and School leadership

This is an opportunity to lead advancement as an enterprise function, aligned closely with the school’s educational mission, financial model, and long-term aspirations.

Strengths of the School

Near North Montessori (NNM) is justifiably proud of its strong sense of community, educational legacy, and deep commitment to Montessori values. Across conversations with faculty, staff, trustees, parents, and Advancement Committee members, the school is consistently described as a place of belonging, shared purpose, and genuine care for children and families. This relational foundation is one of Near North’s greatest assets and a powerful base upon which to build a stronger culture of philanthropy.

Several strengths position the school well for advancement growth at this moment:

• A values-aligned, deeply committed community. Families choose Near North Montessori intentionally—for its child-centered philosophy, commitment to diversity, and urban Montessori experience. There is a longstanding precedent of giving beyond tuition, and the community broadly understands that philanthropy plays a critical role in keeping tuition accessible, supporting financial aid, and sustaining program quality.
• Renewed leadership stability and optimism. With a permanent Head of School in place, the community has experienced a renewed sense of clarity, transparency, and trust. This stability creates an important opportunity to tell a refreshed, forward-looking story about Near North’s impact and future—one that re-engages families who may have stepped back during recent transitions and invites them into the school’s next chapter.
• An engaged and motivated Board and Advancement Committee. Trustees and Advancement Committee members bring a strong sense of fiduciary responsibility and genuine commitment to the school’s long-term health. They are eager to partner with an experienced advancement leader who can provide strategic direction, clarify expectations, and help channel their energy effectively—both in governance and in fundraising leadership.
• Strong participation and event success to build upon. Near North performs well in areas such as parent participation in giving and the net profitability of its major event, Big Night, which is both a beloved community tradition and a meaningful revenue generator. These successes demonstrate the community’s willingness to engage and give when efforts are well-organized, purposeful, and aligned with mission.
• A clear-eyed understanding of what must improve. The school has invested in a comprehensive Advancement Strategic Plan that candidly identifies challenges—including inconsistent attainment of fundraising goals, donor retention, data integrity, and system fragmentation—and outlines a “back to basics” roadmap for progress. This shared understanding creates alignment around priorities and a readiness for disciplined, expert-led advancement work.
• Significant opportunity to strengthen systems, relationships, and impact. With intentional focus on rebuilding trust, strengthening the case for support, improving data and operations, and personalizing donor engagement, Near North Montessori is well-positioned to grow philanthropic results over time—from just over $1 million annually toward its fuller potential of $1.5–$2 million. The school’s mission, community loyalty, and transparency about needs provide a strong platform for this growth.

Taken together, these strengths reflect a school that is not starting from scratch, but rather one that is ready to move from goodwill and effort toward greater consistency, clarity, and sustainability in advancement. To fully realize its potential and sustain its mission for the long term, Near North Montessori is intentionally strengthening its advancement strategy, systems, and leadership. The next Director of Institutional Advancement will have the opportunity to harness these assets, guide the community with confidence, and help build a durable, mission-aligned culture of philanthropy.

Leadership Responsibilities and Opportunities

Reporting directly to the Head of School and working closely with the Board of Directors and Advancement Committee, the Director of Institutional Advancement will hold responsibility for the following areas of leadership:

Strategic Advancement Leadership

• Develop, refine, and execute a multi-year advancement strategy aligned with the school’s mission, values, and strategic priorities.
• Lead annual, major, capital, planned, and legacy giving efforts, ensuring clarity of goals, messaging, and timelines.
• Guide the school toward a focused, achievable fundraising portfolio—currently centered on the Annual Fund, Big Night, and a nearly completed playground capital campaign—while laying groundwork for future initiatives such as endowment.
• Translate strategy into actionable plans with clear benchmarks and accountability.

Donor Cultivation, Solicitation, and Stewardship

• Personally cultivate, solicit, and steward major donors while expanding and diversifying the donor base.
• Strengthen relationships across families, alumni, grandparents, staff, and community partners through thoughtful, personalized engagement.
• Partner closely with the Head of School and Board in donor strategy, preparation, and visits.

Team Leadership and Development

• Lead, mentor, and support a small professional advancement team, fostering a collaborative, mission-driven, and high-performing culture. The team will include the Director of the Near North Fund, Director of Donor and Alumni Relationships, Data Manager, and Communications Manager.
• Clarify roles, expectations, and goals, and support ongoing professional growth and retention.
• Assess team strengths and gaps and make adjustments as needed to ensure sufficient internal capacity.

Operational Excellence and Systems Building

• Build and manage a coherent, data-informed advancement operation, including donor analytics, reporting, and pipeline management.
• Ensure the advancement function is fluent in data—or builds that fluency quickly through hiring, training, or systems improvement.
• Oversee an advancement operating budget (approximately $150,000+), aligning staffing, systems, and fundraising investments with realistic return and capacity.
• Partner closely with Finance to ensure strong integration, transparency, and accountability.

Community Engagement and Storytelling

• Strengthen Near North’s case for support by clearly articulating the school’s impact, values, and aspirations.
• Shape messaging that fosters belonging, gratitude, and shared responsibility.
• Lead advancement communications with clarity and purpose, helping families and donors understand why philanthropy is essential to the school’s mission, access, and sustainability.

Skills, Experience, and Leadership Attributes

Near North Montessori seeks a Director of Institutional Advancement who brings both technical expertise and relational leadership. The ideal candidate will demonstrate many of the following:

• Bachelor’s degree required; advanced degree preferred
• At least five years of successful nonprofit fundraising experience, with a demonstrated record of personally soliciting and closing major gifts
• Experience working in independent schools or mission-driven organizations with sophisticated donors
• Demonstrated ability to establish productive boundaries with boards and volunteers while maintaining strong relationships
• Experience supervising and developing professional staff
• Strategic and analytical thinking, with the ability to use data to inform decisions
• Exceptional interpersonal, written, and verbal communication skills
• High emotional intelligence, discretion, and integrity
• A collaborative, inclusive leadership style and comfort partnering across departments
• Familiarity with fundraising CRMs (Blackbaud preferred) and related tools, or the ability to learn quickly
• Flexibility to work evenings and weekends as required in school advancement work

Above all, the successful candidate will be energized by Near North Montessori’s mission and community, and motivated by the opportunity to help the school thrive for generations to come.

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

How to Apply

Applications will be reviewed when 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 [email protected]

Carol Santos, Partner, Educators Collaborative [email protected]

Near North Montessori believes that each individual is entitled to equal employment opportunity without regard to race, color, religion, gender, national origin, age, disability, genetic information, sexual orientation, ancestry, veteran status, or any other characteristic protected under federal, state, or local anti-discrimination laws. The School’s equal employment opportunity practices extend to recruitment, hiring, selection, compensation, benefits, transfer, conditions, and privileges of employment.