Director of Annual Giving & Communications

Job Summary

The Director of Annual Giving & Communications serves as the primary architect of the school's philanthropic voice and the driver of the $2,000,000 OES Annual Fund. Beyond meeting financial targets, this role is a strategic thought partner to the CAO and the Major Gift team.

This position serves as the hub and coordinator for department communication, ensuring that every piece of communication—from alumni newsletters to campaign proposals—is cohesive, brand-aligned, and strategically designed to support "comprehensive" giving. This role is essential in preparing the groundwork for double and triple asks, ensuring that donors are moved seamlessly through the pipeline from annual support to major and planned gifts.

The director of annual giving and communications holds a key role on the Advancement Team and the OES school community through leading a highly organized and effective OES annual fund program. A skilled, enthusiastic, and collaborative team player, the director is responsible for the planning and execution of a comprehensive annual giving program, including leadership for events designed to build and grow operating support.

The director collaborates with colleagues across the department to build alignment across multiple programs to support shared goals and a shared voice in communicating the work of OES to a variety of donor constituencies.

The successful director excels at meeting with and soliciting individual donors, strategizing with colleagues, volunteer committees, and coordinating complex projects. Discretion and sound judgement are particularly important attributes due to the high degree of access to confidential information and valued relationships. In addition to the qualifications detailed below, the director must possess exemplary people skills, demonstrate curiosity and communication skills to articulate the School’s mission to its constituents.

• Manage a personal portfolio of prospects between $1,000 and $50,000 with a focus on increasing annual giving, special gifts, and connecting OES supporters to major gift opportunities that align with their philanthropic goals.
• Manage a Special Events Coordinator.
• Oversee and continue to grow the OES Annual Fund and leadership giving program (1869 Society), including directing all marketing efforts, stewardship activities, and monitoring of membership.
• Oversee and integrate the annual OES Auction into a comprehensive annual giving program. Develop communications, strategies and goals to underscore the vital impact of annual giving (comprised of both the Auction and the OES Annual Fund, and other current use gift opportunities).
• Work directly with the chief advancement officer, director of development, director of alumni relations, and head of school in cultivation, stewardship and solicitation of major gifts for annual, endowed, and capital campaign programs.
• Oversee all annual giving fundraising activities with a particular focus on individual giving; coordinate annual giving solicitations for all constituencies to maximize giving, participation, and renewal rates; manage and support volunteers in their efforts to solicit peers for both OES Fund donations and Auction donations.

• Comprehensive Proposal Design: Collaborate with the Director of Development and MGO to create "Comprehensive Gift" proposals to ensure that when a donor is asked for a $250k Capital Gift, the proposal includes a clearly defined annual fund participation opportunity and an invitation for a legacy/planned gift.
• Pipeline Intelligence: Act as the "internal scout," identifying donors within the $2M annual fund pool who show markers for major gift capacity and alerting the Major Gift team.
• The…