Westover School (Westover), an independent, college-preparatory boarding and day school for girls in Middlebury, Connecticut, seeks a dynamic fundraiser and team leader with a proven track record to serve as its next Director of Advancement (DOA).
Reporting to the Head of School, the Director of Advancement will oversee all aspects of Westover’s fundraising, alumnae and parent engagement programs, and further strengthen a growing culture of philanthropy. With a deep belief in Westover’s mission and the transformative power of girls’ education, the Director of Advancement will help shape the strategic direction of the advancement office and position the School for its next phase of growth.
This work will be accomplished through the development and execution of a comprehensive, goal-driven advancement strategy, along with the cultivation and stewardship of meaningful, enduring relationships across the Westover community.
About Westover School
Westover School is a girls-centered boarding and day school for grades 9-12. At Westover, students are truly seen for who they are and who they aspire to be, and are celebrated for their intellect, curiosity, and unique passions. This is a community where innovative academics foster intellectual empowerment, collaboration thrives, and faculty inspire bold exploration. Rooted in sisterhood, friendships here are lifelong and unbreakable.
Since its founding in 1909, Westover has been committed to providing a transformational college preparatory education that celebrates and empowers every individual through small classes (the average class size is just 12 students) and rigorous academics (offering 21 AP and Honors Courses) within a small, close-knit community. Westover students are at the heart of their learning journeys. Creative problem-solving connected with deep intellectual curiosity is central to the school’s educational philosophy and academic vision. Today, 200 students enroll, hailing from 20 states and 24 countries. Approximately 67 percent of students identify as students of color, and 68 percent of students are boarding.
Advancement at Westover
Philanthropy is the cornerstone that sustains Westover beyond tuition, fueling the dreams and futures of generations to come. The generous support of Westover’s community empowers students and teachers to reach new heights of creativity, innovation, and excellence, having a profound impact that unlocks opportunities that inspire and transform. The Office of Advancement further supports the mission and strategic goals of the school by keeping alums, parents, the community, and friends connected to Westover. The most recent comprehensive campaign at Westover, the Inspiring Women Campaign, yielded $51.5M for the school, providing exceptional stability for operations and aid in building the endowment. Today, Westover benefits from 100 percent board participation, 100 percent faculty and staff participation, and a steady annual fund, which yields over $2.3M each year.
Director of Advancement
Reporting to and partnering closely with the Head of School, the Director of Advancement will serve as the strategic and tactical leader for all philanthropy and donor relations activities at Westover. In addition to the DOA, the Advancement Office at Westover currently includes a staff of five: Advancement Services Manager, Advancement Projects and Events Manager, Director of the Westover Fund, Families Liaison, and Marketing Coordinator. The DOA will have the opportunity to hire additional staff once on board. The DOA will also serve as the staff liaison to the advancement committee and related subcommittees of the board of trustees and work closely with parent and alumni volunteers, in addition to serving as a key member of the Head of School’s Senior Team.
Candidate Profile
The ideal candidate will have a strong desire to work towards Westover’s mission of empowering young women to lead lives of consequence. While primarily an externally facing role, the next DOA will understand the essentialness of having connections with the daily life of the school, and will seek to embed themselves to both aid in supporting Westover’s students and then share their stories with the broader community. Candidates should hold a bachelor’s degree, with a master’s degree preferred. In addition, the ideal candidate will demonstrate many of the following professional and personal qualities, skills, and characteristics:
- Extensive and successful record of front-line fundraising at a leadership level;
- History of developing, leading, and delegating to a talented team;
- Confidence around and enthusiasm for ambitious campaign planning and execution;
- Dedication to partnering seamlessly with the Head of School and ensuring she is positioned for successful donor and prospect engagement;
- Passion and talent for operating as an inspirational storyteller;
- Desire to be embedded in the campus community;
- Innovative and strategic approach to long-term planning;
- Experience leading or playing a significant role in the planning and implementation of a substantial, comprehensive campaign, including establishing metrics and processes to monitor and evaluate operational performance outcomes, and a commitment to see through the next campaign at Westover;
- Strategic understanding of data management practices and systems, CRM tools (including Raisers Edge), and innovations that can optimize advancement processes and contribute to maintaining high standards of data integrity;
- Unimpeachable personal integrity, including upholding a culture of confidentiality
- Exquisite interpersonal and communication skills; and,
- Is trustworthy and a self-starter.
Compensation and Benefits
This is a full-time position that will be performed on site in Connecticut. Salary is competitive and commensurate with experience. The salary range for this role is $200,000 to $215,000 with a generous benefits package, including housing and potential tuition remission. To learn more about Westover’s offerings, please see their employment page.
DSG | Storbeck has been exclusively retained for this engagement, led by Matthew Marsallo and Anne Koellhoffer. Express interest in this role by filling out our Talent Profile or emailing the search team directly at [email protected]. All inquiries and discussions are strictly confidential.