Director of Advancement and Community Engagement

Cold Spring School; New Haven, CT

About Cold Spring School

Cold Spring School (CSS) is a progressive, independent school in the heart of New Haven, serving children from preschool through sixth grade. Guided by the belief that education is the movement from darkness to light, we see each child as a “person in progress” and nurture curiosity, creativity, and community. With strong partnerships among families, faculty, staff, and trustees, CSS is dedicated to preparing children to be compassionate, capable, and thoughtful citizens.

Position Overview

The Director of Advancement and Community Engagement is a senior leader at Cold Spring School, responsible for strengthening the school’s culture of philanthropy, elevating its visibility, and deepening connections across its vibrant community.

This role brings together fundraising, communications, and relationship-building to support the school’s long-term sustainability and community vitality. The Director of Advancement works in close partnership with the Director, Board of Trustees, and administrative team to align advancement efforts with the school’s mission and strategic priorities.

In the first year, priority will be placed on strengthening the Annual Fund, building a sustainable major donor pipeline, and aligning communications to support both community engagement and enrollment.

Key Responsibilities

Philanthropy & Fundraising

• Design, execute, and evaluate a comprehensive fundraising program, including annual giving, major gifts, campaigns, events, and planned giving

• Manage a portfolio of donors, cultivating, soliciting, and stewarding relationships to support current and future needs

• Partner with the Director and Board of Trustees to identify, cultivate, and engage donors

• Support and guide trustees in their role as ambassadors and partners in philanthropy

• Oversee donor recognition and stewardship to ensure meaningful, lasting connections

• Pursue grant opportunities aligned with the school’s mission

• Use data and metrics to track fundraising performance and inform strategy

Institutional Advancement & Strategic Leadership

• Partner with the Director and Board of Trustees to advance strategic initiatives and financial sustainability goals

• Lead the planning and execution of long-term advancement strategies, including capital and endowment initiatives

• Serve as a member of the Administrative Team, contributing to school-wide leadership and decision-making

• Provide regular, clear updates to the Board of Trustees on advancement progress

Community Relations & Engagement

• Strengthen relationships with parents, alumni, grandparents, neighbors, and community partners

• Cultivate a culture of belonging and generosity across the Cold Spring community

• Represent Cold Spring School at events and in the broader community

• Design and support events that both build community and advance fundraising goals

• Partner with faculty and staff to connect school experiences with community engagement

Communications & Storytelling

• Partner with the Director of Enrollment Management to align messaging across advancement and admissions, with clear roles and shared priorities

• Lead advancement-focused communications, including Annual Fund messaging, donor materials, and community storytelling

• Identify and elevate compelling stories of student learning and community impact to support philanthropy, enrollment, and engagement

• Support the Director with key messages and strategic communications

Alumni & Legacy Engagement

• Build and sustain meaningful relationships with alumni and legacy families

• Develop opportunities for alumni connection, mentorship, and giving

• Foster a sense of lifelong connection to Cold Spring School

Diversity, Belonging, & Inclusion

• Ensure that advancement and communications efforts reflect CSS’s commitment to diversity, equity, inclusion, and belonging

• Engage all community members as valued partners in philanthropy and school life

Operations & Management

• Manage advancement and communications budgets

• Oversee donor databases and advancement systems

• Build and maintain clear, reliable processes to support consistency, accountability, and a strong donor experience

• Coordinate volunteers and support community-based initiatives

Qualifications

• Bachelor’s degree required; advanced degree and/or CFRE credential preferred

• Demonstrated success in advancement, development, or fundraising (independent school or nonprofit experience strongly preferred)

• Experience cultivating and securing major gifts and leading fundraising initiatives

• Strong organizational and project management skills

• Proficiency with donor databases, fundraising tools, and Google Workspace

• Experience working collaboratively with senior leadership and boards

• Passion for progressive education and Cold Spring School’s mission

• Strong relationship-building and storytelling skills

Personal Characteristics

• Relational: Builds trust and connection across a wide range of stakeholders

• Strategic: Sees the big picture while attending to important details

• Creative: Generates ideas and connects them to mission-driven outcomes

• Flexible: Thrives in a dynamic, multifaceted environment

• Clear Communicator: Writes and speaks with clarity, confidence, and warmth

• Collaborative: Works in alignment with the Director and school priorities

• Growth-Oriented: Reflective, curious, and eager to learn

Reporting & Relationships

• Reports to the Director

• Serves as a member of the Administrative Team

• Works closely with the Board of Trustees, faculty, staff, parents, alumni, and community partners

Application Process

Please submit a cover letter, résumé, and list of references directly to Director Jennifer Le Varge [jlevarge@coldspringschool.org]. Applications will be reviewed on a rolling basis until the position is filled.