Director of Annual Giving

Founded in 1886, The Winsor School is an independent girls’ school for academically promising and motivated students in grades five through twelve. Located in the heart of Boston’s Longwood Medical and Academic Research area, our students benefit from the school's longstanding commitment to providing a superior education for girls, inspirational and dedicated faculty, and diverse and talented community. Winsor strives to consciously create an environment of respect and inclusion and to support ethnic, racial, religious and socio-economic diversity among all the constituencies of the school. Winsor supports this commitment through its inclusive curriculum, success addressing a range of learning styles, availability of a wide array of diversity efforts and programs, and participating in the greater Boston community.

Job Description: Director of Annual Giving
Position: Director of Annual Giving
Reports to: Chief Advancement Officer
Department: Advancement
Classification: Exempt, 12-month

Position Summary
The Director of Annual Giving leads the strategic planning and execution of the Winsor Fund to meet revenue and participation goals. Through a multi-channel annual campaign — including direct marketing, volunteer recruitment and management, and direct solicitation — the Director drives annual giving success. This role oversees all aspects of the annual giving program as well as the annual giving team, managing the Associate Director of Advancement Operations and the Assistant Director of Annual Giving. There is also opportunity to elevate reunion giving and weave annual giving messaging into the entirety of the school programming and events.

This is a 12-month position reporting to the Chief Advancement Officer.

Essential Functions
Annual Fund Program and Team Management (35%)
● Plan and execute strategies to set and achieve ambitious annual giving goals.
● Establish, track, and meet specific metrics for donor retention, acquisition, leadership-level upgrades, and dollars raised. Create and track against Winsor Fund gift pyramid.
● Collaborate with colleagues to integrate annual giving, reunion giving, and major gift solicitation strategies.
● Serve as a resource for fundraising staff and volunteers.
● In collaboration with the CAO, prepare reports and presentations for the Board of Trustees, Advancement Committee, Finance Committee, Campaign co-chairs, and other key stakeholders.
● Hire, onboard, lead, coach, and motivate annual giving team, including the Assistant Director of Annual Giving and the Associate Director of Advancement Operations (who is responsible for the gift processing, database, and reporting needs of the office).
● Track and lead the annual giving budget.
● In partnership with the Associate Director of Advancement Operations, leverage data analytics, predictive modeling, and donor database segmentations to identify giving trends, evaluate appeal ROI, and drive data-informed fundraising strategies.
● Collaborate on the creation and execution of a comprehensive stewardship and loyalty program (e.g., consecutive years giving societies) to recognize and retain Winsor Fund donors.

Direct Marketing (10%)
● Drive the development of a communications plan, including timeline, work with mailhouses, appeal signers, etc., for effectively marketing, messaging, segmenting, and executing appeals in collaboration with the Communications department.
● Oversee the Assistant Director of Annual Giving’s work with Communications and the Associate Director’s work as the project manager and lead for annual appeals, appeals communications calendar, managing internal and external deadlines, and organizing input from key stakeholders.
● Oversee the direct marketing strategy behind Giving Day; keep up on modern giving technologies to implement where appropriate.

Portfolio and Prospect Management (15%)
● Manage a small portfolio of lead annual giving prospects, actively identifying, cultivating, soliciting, and stewarding donors to secure leadership-level annual gifts.
● Establish strategic cultivation and solicitation plans for individual prospects within the portfolio, coordinating with major gift officers to align prospect pipelines.
● Prepare timely, constructive, and complete contact reports, proposals, and deliverables for internal stakeholders; deliver timely and effective follow-up to prospects and donors.
● Personally thank donors within the pool for their Winsor Fund gifts. Work collaboratively to maintain a strong stewardship strategy for portfolio donors to encourage donor retention.
● In consultation with the CAO, set a target for number of solicitations per year and a dollar goal for the pool overall.

Volunteer Management (30%)
● In collaboration with the CAO, lead the Annual Giving Committee and other high-level volunteers; strategize and prepare for Committee meetings.
● Lead volunteer recruitment and engagement strategy for annual giving alumnae and parent volunteers; recruit, train, and manage volunteer committees or cohorts to scale peer-to-peer fundraising efforts.
● Serve as liaison with GiveCampus for crowdfunding and volunteer platforms.
● Create meaningful and educational materials (talking points, templates, etc.) to aid volunteers in successful relationship-building and peer solicitations.
● Provide high-level volunteer support to the President of the Winsor Board of Trustees, Annual Giving chair, and other key volunteers, including managing their assignments and staffing meetings.
● In collaboration with the CAO, provide critical support and staffing for the Head of School, Board of Trustees, and annual giving volunteers.

Other Responsibilities (10%)
● Work with the Operations team to ensure timely gift processing and reporting and appropriate planning and implementation of systems and strategies as related to the annual giving program, campaign, and other needs.
● Assist in the operations and logistics for Advancement events and ensure staffing needs are met.
● Participate in appropriate team working groups to accomplish shared goals.
● Provide exceptional collaboration strategy and customer service to all key stakeholders.
● Perform other duties as assigned by the head of school or supervisor.
● Attend mandatory meetings, including, but not limited to, opening and closing meetings, faculty/staff meetings, division meetings, and department meetings.

Required Qualifications
● A Bachelor’s degree.
● At least five years of development/fundraising experience; experience with annual giving and frontline fundraising preferred.
● Demonstrated success managing professional staff and volunteers.

Preferred Qualifications and Skills
● Talent for developing meaningful, genuine relationships.
● Proven track record of soliciting and closing lead annual fund gifts.
● Strong public speaking, presentation, and communication skills.
● A thorough knowledge of Word, Excel, PowerPoint, and preferably Raiser’s Edge or equivalent CRM database.
● Excellent attention to detail as well as organizational, analytical, time management, and problem-solving skills.
● Ability to manage multiple projects successfully in a fast-paced environment.
● Ability to work independently and as a member of a team.
● Proven ability to manage diverse teams, supporting both front-line fundraising/communications staff and technical database/operations staff. Strong commitment to professional development and coaching for team members.
● A passion for Winsor’s mission and for the development profession. Keen understanding of Winsor’s mission and goals and the ability to articulate the school’s uniqueness and relevance.

Work Environment and Physical Demands
● Frequent talking, listening, walking, sitting and standing.
● Ability to perform multiple concurrent tasks and function in a fast-paced working environment.
● Occasional evening and weekend work is required to support key advancement events, committee meetings, and donor engagement opportunities.

The salary range is $120,000–$165,000.

Nothing in this Job Description restricts Winsor’s right to assign or reassign duties and responsibilities to this position at any time.