Director of Development

ABOUT WEST SIDE MONTESSORI SCHOOL

West Side Montessori School (WSMS) is a private, nonprofit school that has provided exemplary Montessori Early Childhood programming to children for over 60 years. Located on the Upper West Side, we serve a richly diverse community of families, faculty, and administrators. Enrolling nearly 250 children from three months through six years of age across two programs in multiple locations: the Early Childhood Program at 309 West 92nd Street and the Infant Toddler Program at 212 West 95th Street. WSMS extends its influence internationally through the WSMS Teacher Education Program, which prepares the next generation of Montessori educators. WSMS is accredited by the New York State Association of Independent Schools and the American Montessori Society.

WSMS seeks an accomplished fundraising professional to be our next Director of Development, who will serve as a strategic thought partner to the Head of School (HOS) and Board of Trustees, while advancing our multiyear Growth Campaign goals and leading the strategic evolution and execution of our Annual Giving initiatives. WSMS has an operating budget of approximately $15 million, an investment portfolio valued at $14M, and $22M in real estate assets. Beyond the current Growth Campaign, this role will be instrumental in building a lasting culture of philanthropy, expanding recurring and multiyear giving, and establishing a sustainable major gifts program that supports WSMS's long-term financial strength.

POSITION OVERVIEW

The Director of Development works closely with the HOS, Chief Financial Officer, and Board of Trustees to align fundraising strategy with WSMS's long-term financial goals. WSMS is in the third year of a $14 million fundraising effort, with $4.3 million raised to date, comprising a $10 million multiyear Growth Campaign goal and a $4 million Annual Giving goal. The ideal candidate has the professional skills and fundraising expertise to build a durable donor pipeline, lead major gift solicitation, and establish a sustainable giving program beyond the current campaign.

WSMS benefits from a highly engaged community, with 100% participation in the Growth Campaign from its Board of Trustees and 95% current parent participation in the Annual Fund. Annual Giving includes the Fall Festival street fair, the Annual Fund drive, and the themed Spring Gala.

KEY RESPONSIBILITIES

Major Gift Solicitation

• Develop and execute personalized donor cultivation strategies that deepen engagement and strengthen long-term relationships.
• Lead the cultivation, solicitation, and closing of significant five- and six-figure gifts, working directly with prospective donors and partnering with the Head of School and Board of Trustees to maximize fundraising opportunities.
• Manage the full gift cycle — identification, cultivation, solicitation, closure, and stewardship.
• Draft gift proposals and agreements tailored to individual donor capacity and giving history. 

Giving Leadership

• Develop and execute a comprehensive, multiyear fundraising strategy integrating the Growth Campaign, Annual Giving, major gifts, and fundraising events, with clear revenue targets, milestones, and performance metrics. Monitor progress against the $14 million goal and report regularly to the Head of School and Board of Trustees.
• Build and expand a sustainable pipeline of current and prospective donors through targeted cultivation, donor segmentation, giving history and capacity analysis, and alumni engagement. Develop personalized strategies to deepen relationships, expand giving opportunities, and secure long-term philanthropic support.
• Lead the Head of School, Board of Trustees, and Pitch Team in executing a structured donor solicitation strategy, including identifying appropriate solicitation leads, assigning prospects, and preparing trustees with comprehensive donor profiles and tailored briefing materials. Establish clear accountability, timely follow-up, and reporting to maintain momentum and drive results.
• Partner with school administrators and parent committees to ensure fundraising events and donor engagement initiatives are strategically aligned, effectively executed, and contribute to the school’s broader fundraising goals. Oversee the development of Annual Giving and Growth Campaign messaging, fundraising materials, and donor-facing communications.

Gift and Data Management

• Oversee accurate recording and tracking of gifts and pledges in Blackbaud Raiser’s Edge NXT, timely acknowledgments, and monthly reconciliation with the Business Office.

MINIMUM QUALIFICATIONS

• Bachelor's degree in a related field required. Experience fundraising in a nonprofit organization and/or independent school setting, with exposure to Montessori education pedagogy, strongly preferred.
• Seven to 10 years of fundraising expertise with a demonstrated track record of successfully soliciting five- to six-figure donor gifts independently or within an active capital campaign construct.
• Tangible experience leading and managing annual giving programs and major gifts initiatives from inception to completion is essential.
• Highly skilled in engaging high-net-worth donors and efficiently reporting measurable results to senior leadership and trustees.
• Proficiency with a donor CRM system (Raiser’s Edge NXT or comparable) and experience coordinating pledge and gift reconciliation with a finance office.
• Demonstrated leadership and team-management experience, with the ability to serve as a strategic partner to senior leadership and the Board of Trustees.
• Strong written, verbal, organizational, and interpersonal skills, with the capacity to work effectively among donor prospects and internal and external constituencies.
• Exceptional attention to detail, sound judgment, and a commitment to timely, high-quality execution.

How to Apply

Email View email address on click.appcast.io with the following:

• Resume
• Cover letter with evidence of successful fundraising, your interest in WSMS, and how your experience meets the qualifications
• Applications will be reviewed on a rolling basis, and we will give priority consideration to applications received by November 13, 2026. 

West Side Montessori School welcomes employees of any race, color, sexual orientation, or national or ethnic origin. We do not discriminate on the basis of race, color, sexual orientation, or national or ethnic origin in administration of our educational policies, hiring policies, scholarship and loan programs, and other school-administered programs.