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Director of Leadership Annual Giving

The Hill School

Pottstown, Pennsylvania

The Director of Leadership Annual Giving (DLAG) is responsible for designing, implementing, managing and coordinating a comprehensive annual giving program that supports the School’s operating budget with unrestricted gifts within The Strength of All Campaign and the overall OIG fundraising operation for the School.

The annual giving program will be a combination of external donor visits with significant Hill Fund donors, an appeal program (digital and direct mail) that reaches our Hill constituency far and wide as well as an annual giving stewardship program that explains and demonstrates gift impact while encouraging donor retention. DLAG partners heavily with our Director of Reunion Giving to secure Hill Fund gifts during the reunion giving cycle as well as partnership with our Capital Giving team to pair major Hill Fund gifts with capital and endowment campaign support.

The Hill Fund annual giving program comprises gifts from alumni, parents and other constituencies. DLAG will lead annual giving strategy and program for all donors to The Hill Fund. He/she will also re-invigorate and assess The 1851 Society, the School’s 11-year old leadership giving society for donors who support The Hill annually with a gift of $1,851 or greater each fiscal year. The 1851 Society is The Hill’s signature giving society with resonance and recognition widely within our Hill community. But, it is in need of assessment.

DLAG must bring a “major gifts” approach to annual giving, realizing that increased Hill Fund gifts result most from personal outreach and deep, meaningful relationships. Explaining the impact of annual Hill Fund gifts and how they will be spent at the School is an essential skill for DLAG. The successful candidate will not only be a lead internal Director of OIG but also a “major gift officer” for The Hill Fund and is expected to make many, significant Hill Fund asks and travel heavily for The Hill Fund from July 1 through June 30 annually.

Hill Fund/Parent Fund appeal design and messaging is managed by the Office of Strategy Management (OSM) and is handled outside of OIG. DLAG will work very close with relevant OSM staff to execute the appeals annually.

In addition, DLAG must collaborate with OIG Directors to determine the best strategies for effective annual giving from alumni and current/past parents; maintain ongoing and active networking with internal and external constituencies; and advise on the facilitation of recognition events and coordinate various activities for donor societies. The position is a key leader in the Campaign and will have significant impact on its success, management and direction along with OIG overall.

DLAG reports to the Assistant Headmaster for Institutional Giving and has a close working relationship with the Directors of Capital Giving, Stewardship and Operations and Reunion Giving as well, given the position’s importance to the Campaign.

DLAG must work closely with all OIG staff and will interact with other prominent and important Hill School leaders, trustees, and our faculty as well as current students.

Specific Responsibilities

  • Work closely with OIG staff who have Hill Fund donors assigned to them to secure larger gifts on a recurring basis.
  • Serve in the top leadership capacity to inspire annual giving for the School and the OIG staff – the “go to” annual giving leader.
  • Manage Hill Fund/Parent Fund mailings/appeals with Office of Strategy Management – mail files, segmentation, data, retention studies and reports on results.
  • Work closely with the Business Office and the Director of Institutional Giving Operations and Stewardship to reconcile and report on Hill Fund giving on a monthly basis.
  • Assess, then design, manage and execute our annual Blue Gray Day giving challenge with OSM staff.
  • Provide reporting and data to IG Committee of the Board on The Hill Fund three times annually at Board meetings.
  • Consider strategies to grow gift minimum from $1,851 to $2,000 or $2,500 in The 1851 Society.
  • Oversee leadership parent giving of current parents within 200 miles of campus.
  • Increase Hill Fund and Parent Fund donors who give at $500-1,850 to $2-2,500+.
  • Manage a personal donor pool of 50-75 donors (alumni and parents) while also managing day to day annual giving operations; heavy travel to visit with donor pool expected.
  • Address giving levels within The 1851 Society and the benefits one gets in the Society.
  • Experiment with digital and hard copy annual appeals as well as staff phonathons to bolster The Hill Fund/Parent Fund.
  • Partner with the Director of Reunion Giving to get the most from our class secretaries and agents in terms of Hill Fund outreach to their classmates and reunion committees.
  • Bring strategies and new ideas on Hill Fund asks as events and within our Alumni Chapter programs.
  • Bring strategies and new ideas for an internal staff Hill Fund campaign as well as our True Blue Faculty Campaign for The Hill Fund.
  • Bring strategies and new ideas on the 6th form (12th grade) class gift campaign annually.


  • Minimum of three to five years’ experience, preferably in independent schools or higher education (or a comparably complex organization), in annual giving, major giving, stewardship, or related fields. Previous experience interacting with donors is mandatory and pivotal.
  • Extremely important are the knowledge and ability to create, execute and/or support, and oversee a comprehensive School-wide annual giving plan, including advising on complex and carefully orchestrated appeals and external outreach for the School’s Hill Fund and Parent Fund donors.
  • Excellent organizational, interpersonal, verbal and written communication skills are essential.
  • Must be able to generate creative solutions for soliciting annual giving donors in order to advance the School’s efforts to grow unrestricted annual giving to meet operating budget needs.
  • Ability to think strategically about donor engagement, giving trends and gift impact that resonates within an annual giving program.
  • Excellent social skills, with large groups as well as with individuals, are required.
  • Proven skills and ability to manage multi-phase projects from inception to completion, including the ability to build consensus among team members and balance multiple concurrent priorities.
  • Ability to work independently and as part of a team.
  • Detail oriented, well organized, focused and goal-oriented, with a high level of initiative and energy, as well as adept at problem solving and using judgment in situations requiring independent initiative and tact.
  • Working knowledge of Raiser’s Edge, InDesign, and Excel – or similar programs – is highly preferred and will be required for DLAG to be successful. Prior use of data analytics to establish and/or evaluate donor retention and giving trends is also highly preferred, if not essential to be successful.
  • Must have a high level of independence in accomplishing the responsibilities of the position. Goals, priorities, and major projects are reviewed and discussed on an on-going basis.
  • Ability to interact comfortably, tactfully, and effectively with varied internal and external constituencies.
  • Must display a high level of maturity and personal integrity and ability to understand, develop, and sustain resilient and dynamic relationships with donors, colleagues, and senior management.
  • Must be able to effectively communicate both verbally and in writing.
  • A bachelor’s degree is required.

The Institution

Founded in 1851 as The Family Boarding School, The Hill School prepares young men and women from across the country and around the world for college, careers, and life. Within a family school environment and a rigorous liberal arts curriculum, young people are challenged to work hard, think and reason, be fulfilled, serve the common good, and be prepared to lead as citizens of the world, uniquely guided by our motto: “Whatsoever things are true.” The student enrollment is 525 students, third form (ninth grade) through post-graduate with 52% boys and 48% girls. There is a 76% to 24% boarding-to-day student ratio; all students must board for one year. Hill students are drawn from 28 states and 28 foreign countries.

The Office of Institutional Giving
The Hill School’s Office of Institutional Giving (OIG) is located in The Class of 1960 Alumni House at 715 East High Street in Pottstown. OIG is comprised of 17 full-time staff. This office is responsible for fostering relationships with alumni, parents, foundations and friends to encourage their support of The Hill’s mission and secure the School’s future. Specific areas addressed by OIG, led by the Assistant Headmaster for Institutional Giving, include capital giving (major and estate charitable giving) from alumni, parents, foundations and friends and The Hill Fund (annual giving to support the operating budget); and advancement services (gift processing, database management, stewardship, donor research and gift reporting). Objectives include encouraging volunteer service to the School and raising funds to support capital projects, programs, operating support, student aid, and the School’s endowment; encouraging a culture of philanthropy among all constituencies; and creating opportunities for alumni/parents to stay connected with the School and network with peers.

The OIG is also leading the largest, most ambitious and comprehensive fundraising campaign in The Hill’s history – started on July 1, 2014 – The Strength of All Campaign. Seeking to raise at least $100 million, the campaign is expected to last until July 2024 and bolster the endowment, Hill Fund, campus, and the greater Pottstown community.

The Hill Fund runs from July 1 through June 30 annually and seeks mainly unrestricted gifts to support our School’s operating budget. The FY18 Hill Fund secured $3.71 million in unrestricted and restricted gifts, with $3.51 million unrestricted and $200,000 restricted. 22% of our solicitable alumni made and 38% of current parents made a gift to The Hill Fund/Parent Fund. The Parent Fund is a subset of The Hill Fund. For FY19, the goal is $3.65 million in unrestricted gifts from alumni and parents combined, but $1 million from non-alumni parents inclusive of the total goal. The 1851 Society, The Hill’s leadership giving society that drives 95% of The Hill Fund goal, has 800 members and is eleven years old.

OIG believes The Hill Fund should be at the $5 million range annually as the Campaign gains momentum and large-scale capital and endowment gifts slow in the coming years as priorities are met for The Strength of All Campaign, with gift support flowing back into and increasing to The Hill Fund overall. The new Director of Leadership Annual Giving (DLAG) will lead this initiative and unprecedented growth in annual giving at The Hill.

For additional information about The Hill School, please visit

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