Associate Director of Annual Giving

Greenwich Country Day School • Greenwich, CT

1d

About The Position

Greenwich Country Day School is an independent, co-educational day school with a current enrollment of over 1400 students in grades N-12, and a faculty and staff of over 350. The original Old Church Road campus is home to grades N-8. The High School, established in 2019, is located less than two miles away on Stanwich Road. Founded in 1926, Greenwich Country Day School is a family school where innovative teaching is encouraged as teachers model and foster a love of learning, challenge and inspire children toward academic excellence, and cultivate students’ interests and talents outside of the classroom. We value purposeful and personal learning in a joyful environment, with emphasis on the development of character, creativity, and a sense of personal value along with strong academic skills. GCDS is committed to graduating ethical, confident leaders who possess a strong sense of purpose. GCDS is fortunate to have built a large endowment which helps to fund competitive salaries and benefits, a robust professional development program, and reimbursement for graduate school tuition. GCDS offers a substantial need-based financial aid program to support students from a range of socio-economic backgrounds. Greenwich Country Day School (GCDS) seeks to hire a strategic and data-driven Associate Director of Annual Giving to join our Advancement Team on April 1, 2026 , to oversee the annual giving program, the Tiger Fund. The Associate Director plays a key role in advancing GCDS’s philanthropic goals by developing and executing strategies to increase Annual Fund support from parents, alumni, parents of alumni, grandparents, and friends. Reporting to the Director of Advancement, the Associate Director leverages a range of digital channels—including video, email, text, social media, phone, and virtual meetings—to cultivate relationships, solicit gifts, and steward donors through personalized outreach. The primary focus of this role is to manage and grow a portfolio of Annual Fund donors and prospects, with a strong emphasis on upgrading giving levels and identifying individuals with major gift potential. Additionally, this position supports key reunion fundraising efforts in conjunction with the Alumni Relations team, directs segmented outreach, and leads digital fundraising campaigns. As GCDS enters its second century, the school is preparing to launch a comprehensive capital campaign. The Associate Director of Annual Fund will work closely with the Director of Campaigns to coordinate Tiger Fund solicitations as part of larger gift conversations.

Requirements

• Bachelor’s degree
• 5-10 years of fundraising or related experience, preferably in independent school education or non-profit sectors
• Demonstrated success in annual giving, donor engagement, and/or digital fundraising
• Proven ability to develop and execute fundraising and/or marketing campaigns with measurable success
• Experience with CRM databases (e.g., Raiser’s Edge) and digital fundraising platforms

Nice To Haves

• Excellent communication skills (oral and written) and the ability to engage varied audiences
• Strong interpersonal, relationship-building, and creative problem-solving skills
• Ability to analyze and summarize data, recognize patterns and significant data points, and make recommendations based on the information
• Collaborative team player with a positive outlook, strong sense of initiative and creativity, and a commitment to the School’s mission and values
• Highly organized with attention to detail and the ability to manage multiple projects
• Technologically adept; proficient in Google platforms and able to learn new systems quickly
• Occasional travel and evening/weekend work required

Responsibilities

• Lead all annual giving strategies to grow revenue through the Tiger Fund.
• Manage portfolio of donors who have the capacity to make leadership annual gifts of $7,500
• Manage and staff the Tiger Fund Committee, composed of volunteer solicitors across all constituencies - current parents, current grandparents, alumni, parents of alumni.
• Solicit Tiger Fund gifts using multi-channel strategies, including digital (email, text, video, social), phone, and in-person visits.
• Design and implement communication and marketing strategies for direct mail and digital programs, including solicitation, social media, giving challenges, and other programs as determined
• Direct segmentation strategy to deliver well-timed appeals.
• Collaborate with Advancement Gift Manager, Advancement Operations, and Communications team to manage mailing lists and ensure timely execution of solicitations.
• Work with the Gift Manager to ensure that gifts are accurately and completely recorded in a timely manner
• Oversee the functionality and performance of online giving platforms, such as Give Campus, as needed.
• Maintain detailed and timely records of all fundraising activity using the School’s CRM - Raiser’s Edge/Blackbaud.
• Collaborate with the Stewardship Associate Director in key annual fund cultivation and stewardship events.
• Represent the Advancement Team at key events, including donor events, Homecoming/Alumni Reunion Weekend, and other advancement-related events

Benefits

• GCDS is fortunate to have built a large endowment which helps to fund competitive salaries and benefits, a robust professional development program, and reimbursement for graduate school tuition.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level