Director of Annual Giving

Posted on 08/24/2023

Bennington College

Bennington, VT

Bennington College invites applications for a dynamic and highly engaged Director of Annual Giving position that will align fundraising programs during an opportune time of growth, reimagination, and reinvigoration.

The Director of Annual Giving is a key member of the advancement team at Bennington College, reporting to the Associate Vice President for Development and overseeing all aspects of the Annual Giving program. The Director will lead the strategic direction and operations of the Annual Giving team. This includes creating and managing a detailed annual fundraising plan; developing forward-looking strategies and compelling messages to leverage alumni, parent and student support for the Bennington Fund to ensure its continued growth; reimaging and expanding our volunteer fundraising program for leadership donors; and managing a modest prospect portfolio of leadership donors who make annual gifts between $1,000 and $10,000 and/or are alumni leaders. As part of this work, the Director will initiate and drive, in collaboration with Communications, the message and design of all Bennington Fund materials and appeals.

The Director of Annual Giving serves in a critical leadership role within Institutional Advancement, providing strategic oversight of the annual fund program, partnering with multiple stakeholders to find new ways to inspire support for the Bennington Fund, while building systems internally to effectively interface with departments on campus to develop meaningful giving opportunities. They will oversee a growing staff that works collaboratively across all departments within advancement as well as the Communications Office, the Business Office, and other units on and off campus. Representing Bennington to various constituencies, they have overall responsibility for program growth that aligns with Bennington’s ambitious goals. Some travel required.

General Responsibilities

  • Design, implement and strategically execute a comprehensive annual solicitation program to achieve annual fundraising goals and expectations.
  • Provides strategic direction and long-range/short-range planning for all constituents in the context of growing the annual giving program while supporting the greater development and campaign goals of the college.
  • Manage a small portfolio of leadership donors and prospects ($1,000+). Engage prospects through personal meetings, strategic events, meetings with senior administrators and/or senior members of the Bennington Community.
  • Management of the Annual Giving team, consisting of up to two direct reports.
  • In partnership with the Director of Stewardship and Donor Relations, develop and execute a plan to strengthen the Bennington Fund’s giving societies, including branding, marketing materials, establishing leadership giving levels, and recognition.
  • In collaboration with the Director of Alumni and Constituent Engagement and the Communications department, develop and execute new ways of engaging alumni, parents, and students through social media, electronic communications, events, videos, etc.
  • Partner with the President, Provost and other members of the College’s leadership team to align the goals of the College to the goals of the Bennington Fund; and, develop fundraising campaigns that support these goals.
  • Collaborate with major, planned and principal giving officers regarding high-level annual fund cultivation, solicitation, and stewardship strategies
  • Communicate effectively the programs and needs of the College to alumni, parents and friends in a manner that increases the public awareness of the College’s priorities.
  • Manage vendor relationships and contracts.

Bennington serves a diverse student population inclusive of members of ethnically/racially minoritized, international, LGBTQIA+, and disability communities as well as diverse gender identities, socioeconomic backgrounds, religions, and political beliefs. Our staff and faculty also reflect diverse and intersecting backgrounds and identities. All employees are expected to be respectful and responsive to these differences in the service of building community that promotes student and employee success and community cohesiveness. Each individual (faculty, staff and students) will be accountable for upholding these values. The College’s approach to pluralism and inclusivity—both as fields of inquiry and practice—is to prioritize flexible thought, and to invite the examination of access, value, power, and privilege through its institutional policies and areas of study. We encourage applicants from diverse realms of interest, backgrounds, experience, and accomplishment to apply.


  • Candidates should possess a bachelor’s degree with a minimum of 4-6 years in development with increasing programmatic responsibilities in Annual Giving. Preference for candidates with a background in higher education and experience with direct mail and strategic planning.
  • Demonstrated exceptional organizational skills with ability to manage multiple assignments at once, prioritize opportunities, create and implement a strategic plan, and accomplish major programs and projects.
  • Orientation as a team player and leader with strong management skills, including a metrics-driven, entrepreneurial mindset that informs strategy and work.
  • The ability to succeed in a distinct and dynamic culture.
  • Knowledge of and commitment to the principles of fundraising and donor cultivation.
  • Volunteer engagement and prospect management experience, preferably in an educational setting.
  • Ability to easily network and establish rapport and connections with individuals and groups, including vendors.
  • Excellent communication skills with the ability to engage, motivate, and inspire (in person and in writing).
  • Ability to maintain a high level of diplomacy, and to work independently as well as part of a team.
  • Demonstrates self-awareness, cultural competency and inclusivity, with the ability to work with colleagues and stakeholders across diverse cultures and backgrounds with a commitment to the mission and values of​ Bennington College.
  • Demonstrates self-awareness, cultural competency and inclusivity, with the ability to work with colleagues and stakeholders across diverse cultures and backgrounds with a commitment to the mission and values of Bennington College.
  • An advocate for diversity.
  • Flexibility and the ability to work well within a team of diverse individuals
  • Proficiency with databases, spreadsheets and ability to analyze data, Microsoft Office Suites, and creative design applications, preferably with Google Suite and Blackbaud’s Raiser’s Edge.
  • Travel, evening and weekend responsibilities are required.
  • A hybrid remote work schedule is possible with significant on-campus presence during constituent events.
  • The position requires successful completion and acceptable results of a background check.

The College

Bennington College offers a comprehensive benefits program (to eligible employees) that includes medical, dental, vision, life and long-term disability insurance, retirement, and tuition benefits including Tuition Exchange scholarships. The College also offers an on-site fitness center as well as generous time off benefits (4 weeks of vacation, 10 sick days and 17 paid holidays).

Bennington College is a laboratory for innovation in higher education. At Bennington, learning and making—on campus and in the field—are inseparable, and its graduates are noted for their outsized impact on the world’s stage. This campus celebrates the ongoing making of work—shared on walls, in shows and performances, in lectures and readings, and in conversations—and believes that equity, diversity, and inclusivity are vital to a collaborative community. This position captures, contributes to, and reflects the ethos of this creative community.

Nestled at the foot of the Green Mountains in Vermont, the campus consists of approximately 370 acres. The College was named one of ten with the best architecture by Architectural Digest. From campus, it is a short drive to the cultural offerings of the northern Berkshires in Massachusetts, Albany, New York, and many of Vermont’s top recreational centers. New York City, Boston, and Burlington, Vermont are all within three and a half hours by car.

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