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Director of Engagement and Philanthropy

Fairfield Country Day School is seeking a strategic and relationship-driven Director of Engagement and Philanthropy to lead our school's philanthropic and community engagement efforts.
Reporting to the Head of School and working in close partnership with the Board of Trustees, this leader will design and execute a comprehensive advancement strategy that spans annual giving, major and planned gifts, capital campaigns, and endowment growth. The ideal candidate combines proven fundraising expertise with strong leadership skills, building a culture of philanthropy among faculty, families, alumni, and trustees while closely collaborating with the Enrollment and Marketing and Communications Offices. This is a unique opportunity for an accomplished development professional to shape the future of our School through meaningful donor relationships, sound strategy, and community-wide engagement. 

Advancement Strategy & Leadership

  • Partner with the Head of School and Board of Trustees to develop and implement a comprehensive advancement plan aligned with institutional priorities.
  • Assess current advancement programs and recommend improvements in fundraising, communications, and community engagement.
  • Provide leadership and support to advancement staff, consultants, and volunteers.
  • Collaborate closely with faculty, administration, and the Board to advance a culture of philanthropy.
  • Collaborate closely with Marketing, Communications, and Enrollment

Development & Fundraising

  • Philanthropy & Fundraising: Design and execute multi-year fundraising strategies including annual giving, capital campaigns, major and planned gifts, and endowment growth.
  • Donor Cultivation: Directly manage a portfolio of major donor prospects (alumni, parents, grandparents, and trustees), 
  • Lead the solicitation, stewardship, and recognition processes.
  • Maintain and strengthen relationships with current donors while identifying new prospects.
  • Partner with the Head of School and Board members on donor strategy and solicitations.
  • Ensure accurate gift processing, acknowledgment, and donor stewardship practices.
  • Monitor and report on fundraising progress, metrics, and goals.
Core Responsibilities
  • Constituent Engagement: Supervise efforts to deepen relationships with all community stakeholders, fostering a culture of sustained involvement and giving.
  • Team Leadership: Recruit, mentor, and evaluate advancement and communications staff.
  • Data-Driven Strategy: Ensure the integrity of donor databases and utilize performance metrics to measure success and identify new donor pipelines
  • Provide regular reports to Head of School, Board of Trustees, and Administration
  • Collaborate on the development and execution of an integrated marketing and communications plan
  • Strengthen engagement among parents, alumni, grandparents, and the broader community.
  • Oversee planning and execution of school events that support both community-building and fundraising goals.
  • Partner with parent associations and volunteer groups.

Board Relations

  • Support the Advancement Committee of the Board of Trustees.
  • Provide regular updates on advancement activities, goals, and outcomes.
  • Assist in engaging trustees in fundraising and ambassador roles.

Operations & Systems

  • Oversee advancement systems, including donor databases.
  • Ensure data integrity, reporting accuracy, and compliance with best practices.
  • Manage the advancement budget and track expenses and ROI.
  • Document processes and provide recommendations for long-term sustainability.
Qualifications: 
  • Bachelor’s degree required; advanced degree preferred.
  • 5–10+ years of experience in advancement, development, marketing, or related fields.
  • Demonstrated success in fundraising, particularly annual giving and major gifts.
  • Strong writing, editing, and storytelling skills.
  • Experience managing multiple communication platforms and campaigns.
  • Ability to think strategically while executing tactically.
  • Excellent interpersonal skills with the ability to engage diverse stakeholders.
  • Experience in independent schools or nonprofit organizations is preferred.
Key Compentencies
  • Strategic thinking and adaptability
  • Strong project management and organizational skills
  • Relationship-building and emotional intelligence
  • Initiative and problem-solving in a fast-paced environment
  • Discretion and professionalism
  • Ability to manage a team
  • Enthusiasm about being part of a Kindergarten-Grade 9 boys school community
To Apply
 Interested and qualified candidates are invited to contact FCDS.  Please provide:
  • A cover letter and current résumé
  • A list of three professional references with name, relationship, phone number, and email address of each (references will not be contacted without the candidate’s permission) to:
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Fairfield Country Day School

2970 Bronson Road, Fairfield, CT 06824
Fairfield Country Day School (FCDS) is a private, all-boys day school in Fairfield, Connecticut.

FCDS admits students of any race, color, national and ethnic origin to all the rights, privileges, programs, and activities generally accorded or made available to students at the school. It does not discriminate on the basis of race, color, national and ethnic origin in administration of its educational policies, admissions policies, scholarship programs, and athletic and other school-administered programs.

FCDS is an equal opportunity/affirmative action employer with a strong commitment to diversity and inclusion. We prohibit discrimination on the basis of race, color, religion, sex, age, national origin, sexual orientation, gender identity or expression, disability, veteran status, marital status, or any other legally protected status.