Director of Finance & Operations

The Hill School, Middleburg, VA



The Hill School is an independent, co-educational JK-8 day school founded in 1926 and is located on a 137 acre campus overlooking the historic town of Middleburg, Virginia. The school emphasizes a strong academic program and universal participation in athletics, fine and performing arts, and a place-based education program. In addition to administrative and classroom buildings, the campus includes a performing arts center, an art building, a music and lunchroom building, a natural science center, five athletic fields, a one-mile jogging trail, an outdoor amphitheater, an arboretum, and an abundance of natural spaces. The Hill School is a non-profit organization (501c3) operated under the guidelines of the Commonwealth of Virginia and is accredited by the Virginia Association of Independent Schools.



The Hill School is a high-touch, service-rich environment that fosters openness and trust between administration, faculty, parents and students. Every staff member is deeply committed to the school’s mission and takes a hands-on approach to ensure that students have a rich and fulfilling academic experience. The culture prizes honesty, humility, empathy and compassion balanced with forthright communication and sensible expectations. Successful employment at The Hill School means exhibiting these qualities with everyone, every day.



This is an exciting opportunity for a mission-driven accounting/finance leader to build on the groundwork laid by The Hill School’s long-tenured business team. (Note: The reason for this opening is due to three upcoming staff transitions, including two retirements.) In the new staffing structure, the Director will be an integral partner with the Head of School, Assistant Head of School, and the development team to bolster financial operations in support of continual student recruitment and fundraising efforts.
This pivotal role will direct financial strategy, accounting, facilities and human resources. The school currently manages a $6M operating budget and $14M in endowments, and owns 15 homes on and off-campus for faculty and staff. The Director will supervise the Assistant Business Manager who will handle student contracts and billing, and provide support for facilities management and human resources.



This is a critical leadership role for the continued financial health of the school. Financial responsibilities will include financial analysis, budgeting, accounting oversight, examining tuition levels, financial aid application review, multi-year projects, scenario planning, revenue strategy, capital planning, risk management, debt management, financial reporting, audit oversight, internal controls, investment management and endowment tracking. Additionally, the new Director will liaise with the Finance and Endowment Committee and will deliver periodic presentations to the Board of Trustees.

Essential Duties and Responsibilities:

  • Lead all financial functions of the school, including accounting, audit, internal controls, banking and debt management, investments, budgeting (operating and capital), tracking budget vs. actuals, variance analysis, forecasting, reporting, and overall analytical support for the financial aspects of strategic planning.


  • Work closely with the Head of School, the Assistant Head of School, the Assistant Business Manager, the Finance and Endowment Committee, and the Board of Trustees in developing the annual budget, setting tuition levels, recasting the 3-year plan, monitoring investment performance, updating the investment policy, and in the analysis of all other financial initiatives of the school.


  • Assist Assistant Business Manager and Head of School in all areas of human resources including issuing employment contracts and managing the benefits program (health insurance, retirement, housing, professional development and other benefits provided to employees).


  • Coordinate work in advance of the annual audit to ensure all necessary working papers and supporting documentation are available throughout the audit cycle and during the preparation of the Form 990 and 990T tax returns.


  • Oversee or assist with risk management activities, such as insurance administration and annual renewals, crisis management plan updates and drills, transportation schedules, approved drivers, fire alarm and sprinkler system inspections, and other safety and security measures, as needed.


  • Coordinate with Development office to set goals, track progress, and reconcile pledges and gifts.


  • Negotiate contracts and manage relationships with outside vendors and contractors for services ranging from HVAC maintenance and janitorial services to equipment leasing and IT support.


  • Work with the Assistant Business Manager and other members of the Financial Aid Committee to review financial aid applications and determine appropriate awards for the upcoming school year.


  • Handle or supervise all other Business Office activities, including student billing, collections, purchasing, payables, cash receipts, payroll and financial reporting.


  • Other related duties and participation in school activities in keeping with what is expected of other Senior Administrators.


  • Work with the Assistant Head of School to create contracts and build revenue related to auxiliary income and facility use, as well as Summer Programming.



  • Bachelor’s degree or equivalent in Business Administration, Finance or Accounting
  • Professional knowledge of GAAP, compliance, and internal controls
  • Significant experience leading accounting and financial management.
  • Experience in private school or nonprofit accounting setting a plus



  • Proficient with Microsoft Office applications, Excel in particular
  • High level of skill utilizing accounting software; Blackbaud preferred
  • Ability to develop reports, spreadsheets, and other business correspondence and to present information to applicable constituencies effectively
  • Ability to read, analyze and interpret legal and other technical documents



  • Strategic, business mindset, yet skilled at diving into granular issues
  • Collaborative working style, and able to build rapport with diverse audiences
  • Able to set clear boundaries and build a cohesive, accountable business culture
  • Outstanding organizational and time management skills
  • Willingness to mentor other staff on accounting and budgeting as needed
  • Can-do attitude and flexibility to pivot from “the strategic” to “the mundane”
  • Sense of humor, patience, empathy, humility and integrity
  • Strong work ethic and availability to work several evenings/month and occasional weekends
  • Supportive of Hill School’s mission and enthusiastic to be part of the community
  • Commitment to professional growth, including networking with other like schools and participation in association activities



This is a retained search. All applicants must submit a well-crafted cover letter stating why this opportunity and organizational mission is aligned with their career goals; and a customized resume highlighting key competencies mentioned in this job announcement.  NOTE: for staff cohesion, this is an on-site position with occasional remote working. Send application to Shira Harrington, Purposeful Hire,