Director of Development

ABOUT WEST SIDE MONTESSORI SCHOOL

West Side Montessori School (WSMS) is a private, nonprofit school that has provided high-fidelity Montessori Early Childhood programming to children for over 60 years. WSMS currently operates two campuses serving over 230 children, ages 3 months to 6 years old.

In September 2025, WSMS reached a milestone after successfully opening a new building at 212 West 95th Street, expanding programming to include Infants and Toddlers serving its youngest learners, children ages 3 months to 2 years. WSMS is in its third year of a $14 million Campaign, $4 million from Annual Giving and $10 million from the Capital Campaign. The Board of Trustees has committed 100% participation in the Capital Campaign. To date, $4.3 million of the $14 million Campaign goal has been raised.

POSITION OVERVIEW

WSMS seeks an accomplished fundraising professional to serve as Director of Development, with primary responsibility for advancing the Capital Campaign and leadership of Annual Giving. Annual Giving includes the Annual Fund and two events, the Auction and the Fall Festival. This role focuses on building and sustaining meaningful relationships with current and prospective donors, and ensuring the fundraising pipeline is strong, organized, and mission-aligned. The Director will also pioneer innovative approaches to fundraising and scale new and creative opportunities to expand support and grow our donor network

This is a frontline solicitation role. The Director of Development will carefully curate a portfolio of major gift prospects, lead solicitation directly, and guide members of the Board of Trustees in soliciting gifts within their own networks.

The Director works closely with the Head of School and a fully committed Board, manages gift processing and donor records directly, and partners with administrative staff and parent committees on event planning and execution. Evening and weekend work is occasionally required, including the Auction, the Fall Festival, and donor events.

The ideal candidate is a seasoned nonprofit fundraising professional who knows how to move donors through the giving journey with authenticity, data, and purpose, and who is comfortable working independently. This is a rare opportunity to help shape the next phase of a campaign at a respected school at a pivotal moment, with real influence over strategy, messaging, and pacing.

KEY RESPONSIBILITIES

Major Gift Solicitation

• Develop and execute personalized donor cultivation strategies that deepen engagement and strengthen long-term relationships
• Cultivate, solicit, and close gifts from a personal portfolio of Campaign prospects, with a focus on gifts of $25,000 and above
• 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

• Direct Annual Giving and Campaign fundraising strategies, including pacing against the $14 million goal, timelines, and key performance metrics
• Report Annual Giving and Campaign progress regularly to the Head of School and Board of Trustees
• Recommend appropriate solicitation leads for Board members and prepare trustees for donor conversations, including briefing materials on donor history, capacity, and recommended ask amounts
• Support the creation of Annual Giving and Campaign messaging and donor-facing material

Gift and Data Management

• Process and record gifts and pledges in Blackbaud Raisers Edge NXT, including gift status, pledge terms and next steps
• Issue timely gift acknowledgments and maintain accurate donor records
• Reconcile pledge and gift records monthly with the Business Office

QUALIFICATIONS

Required

• At least seven years of frontline fundraising experience, including a demonstrated record of personally closing gifts of $25,000 and above
• Experience managing an annual giving program
• Direct experience soliciting gifts within an active capital campaign
• Demonstrated ability to engage high-net-worth donors and to brief board members effectively
• Proficiency with a donor CRM system (Raisers Edge NXT or comparable)

Preferred

• Experience in independent school or early childhood education fundraising
• Familiarity with Montessori education
• Experience coordinating pledge and gift reconciliation with a finance office

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.

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