Director of Development and Communications

Search being conducted by DovetailED Talent Sourcing

Advancement, Communications & Alumni Relations Wilmington, DE Posted Mar 12, 2026

$80,000 - $100,000

The Pilot School

Job Description

The Director of Development and Communications is responsible for planning, leading, and executing all fundraising, advancement, marketing, and communications strategies for The Pilot School. Reporting directly to the Head of School, the Director serves on the Senior Leadership Team and works closely with the Board of Trustees, faculty, staff, families, and external partners to ensure the school’s long-term financial sustainability and the strength and clarity of its mission-driven messaging.

The Director oversees all development functions typical of an independent school, including annual giving, major gifts, donor stewardship, events, and advancement operations. In addition, the Director leads all communications and marketing efforts, serving as steward of the school’s brand, voice, and public presence. While some marketing functions—primarily digital marketing—are supported through an external firm, the Director maintains strategic oversight and accountability for all messaging, campaigns, and outcomes.

The Director of Development and Communications manages and supports a team of two and plays a central role in shaping how the Pilot community understands, supports, and champions the school’s mission of unlocking the potential of every student.

Application Instructions

The Pilot School has engaged DovetailED to lead this search. Interested candidates should email a cover letter (addressed to Head of School, Alli Williams), a resume, and a list of at least three professional references consolidated as a single PDF document to Lynda Hamilton-Kirk at lynda@doevtailedsourcing.com.

Job Details

Region Mid-Atlantic (DC, DE, MD, VA, WV)
Location
Wilmington , DE
Salary Range
$80,000 - $100,000
Category Advancement, Communications & Alumni Relations
Posted
Mar 12, 2026