Director of Marketing And Development

The Pilot School , Wilmington, DE

How to Apply

The Pilot School has engaged DovetailED to lead a search for a Director of Development and Communications. Interested candidates should review the and submit a cover letter, resume, and list of references as a consolidated PDF to Lynda Hamilton-Kirk at View email address on click.appcast.io .

The Pilot School is a K-8 independent school for bright students who learn differently. We are situated on a state-of-the art 50- acre campus in Northern Wilmington, and our property abuts Brandywine Creek State Park. Every classroom features floor-to-ceiling windows that look out on green space, so your daily view is a 2,000-acre expanse of forested nature! We believe in a high standard of excellence for our programming, and our faculty rises to the occasion every day.

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.

ESSENTIAL DUTIES AND RESPONSIBILITIES

• Support and carry out the school’s mission and culture
• Design, implement, and oversee a comprehensive fundraising program, including the Annual Fund, major gifts, leadership giving, special initiatives, and advancement events
• Cultivate, solicit, and steward relationships with current and prospective donors, foundations, and community partners
• Partner closely with the Head of School and Board of Trustees to support trustee engagement in fundraising and donor outreach
• Oversee donor stewardship, recognition, and reporting to ensure a strong culture of gratitude and long-term relationship building
• Manage all advancement operations, including gift processing, prospect tracking, reporting, and data integrity, in collaboration with the Business Office
• Develop and oversee the school’s communications and marketing strategy to ensure clear, consistent, and mission-aligned messaging
• Serve as steward of the school’s brand, voice, and visual identity across all platforms
• Oversee internal and external communications, including community letters, newsletters, campaign materials, annual reports, press communications, and major announcements
• Provide strategic direction and project management for the school’s external marketing firm, with particular focus on digital marketing and enrollment-related campaigns
• Collaborate with admissions, faculty, and administrative leaders to communicate the school’s programmatic strengths and successes
• Analyze fundraising and communications data and report progress and outcomes to the Head of School and Board of Trustees
• Supervise, mentor, and evaluate the development and communications team, fostering a collaborative and mission-driven work culture
• Develop and manage departmental budgets and timelines
• Demonstrate professionalism in attitude, attendance, behavior, and work habits

How to Apply

The Pilot School has engaged DovetailED to lead a search for a Director of Development and Communications. Interested candidates should review the and submit a cover letter, resume, and list of references as a consolidated PDF to Lynda Hamilton-Kirk at View email address on click.appcast.io .