Chief Advancement Officer
Job Details
Westchester Lower School - WHITE PLAINS, NY

Chief Advancement Officer

At The Windward School, we are committed to helping students with language-based learning disabilities achieve their full potential in preparation for a successful return to a mainstream educational environment.  Located in White Plains, NY, and Manhattan, NY, The Windward School educates more than 900 students on three campuses.



The Windward School is a coeducational, independent day school dedicated to providing a proven, research-based instructional program for children with language-based learning disabilities. The multisensory curriculum is designed for students of average to superior intelligence who can benefit from the unique educational experience provided.



The Windward School is nationally recognized for its development of instructional programs and best-in-class teacher professional development. In January 2020, the School will launch The Windward Institute, which is dedicated to increasing childhood literacy and disrupting the status quo in education through providing professional development for The Windward School, educators, clinicians, parents/guardians, and non-Windward students; advocating for the rights of students with language-based learning disabilities; building leading-edge education-research partnerships; and expanding the reach and impact of the proven methodology of The Windward School.


This is an exciting time for Windward as Head of School Jamie Williamson leads Windward into the next chapter of its nearly 100-year history. This includes not only the launch of The Windward Institute but also the construction of a new campus for the Westchester Lower School in White Plains. This new campus will impact more lives by creating 150 additional seats for students on both Westchester campuses, serve as the administrative hub for the School and The Windward Institute, and expand Windward’s impact and reach into the community.


The Windward School recently launched the quiet phase of the Next Chapter Campaign, which will significantly expand the impact of The Windward School. Due to the growth of Windward and the increasing complexity of communications and development needs, Windward’s leadership decided to shift to an Institutional Advancement model that will unify communications and development under the leadership of the new Chief Advancement Officer.


This is an excellent opportunity for a transformational leader to partner with a talented Head of School, a dedicated board of trustees, and a hard-working advancement team.



The Windward School seeks a talented Chief Advancement Officer to work closely with the Head of School, board of trustees, and executive leadership team to help lead Windward through a period of growth and development. 


The Chief Advancement Officer will be responsible for advancing Windward’s life-changing mission by developing a unified strategy to increase, diversify, and sustain support for the School.


The Chief Advancement Officer will build and maintain strong relationships both internally and externally, demonstrate a track record of fundraising success, and possess the leadership and managerial acumen necessary to galvanize the full advancement team, providing day-to-day oversight and leadership to the School’s advancement programs among both individual and organizational constituents (including trustees, alumni, parents/guardians, friends, corporations, foundations, community leaders, and others).


This leader will be expected to follow advancement best practices and to be an experienced manager.


Scope of the Role

The Chief Advancement Officer is responsible for leading all aspects of institutional advancement at Windward: communications, development, alumni relations, and special events. Reporting directly to the Head of School, the Chief Advancement Officer will be a member of the senior leadership team.


The Chief Advancement Officer will set the strategic direction for institutional advancement at Windward and serve as a strategic thought partner for the Head of School.



Management of Institutional Advancement

  • Provide clear vision, supervisory leadership and management, and strategic direction for all aspects of Windward’s institutional advancement work
  • Represent institutional advancement as a member of the senior leadership team and at meetings of the board of trustees
  • Develop an annual comprehensive advancement plan in support of the strategic plan
  • Communicate Windward’s mission, vision, and values both internally and externally
  • Work with each member of the institutional advancement team to set clear goals, provide the necessary supervision and resources for them to meet those goals, and foster a sense of ownership over outcomes
  • Build a culture of inclusiveness and teamwork





  • Together with the director of communications, plan and implement a long-term communications plan to include internal and external communications that is reviewed and updated annually
  • Oversee annual communications calendar
  • Ensure coordination between communications, development, and alumni relations staff
  • Serve as a public spokesperson and representative for the School
  • Build and maintain relationships with other independent schools, educational institutions, and community leaders



  • Together with the director of development, ensure that the resources are in place to support the School’s long-term vision and growth by designing and implementing fundraising strategies to support current and future operations
  • Oversee planning for all existing fundraising efforts including the gala and other special events, the Windward Fund, the Next Chapter Campaign, and alumni giving
  • Develop strategies for new funding streams including grants and planned giving
  • Evaluate fundraising performance and identify ways to increase fundraising totals and expand philanthropic revenue sources
  • Cultivate, solicit, and steward a small portfolio of major donors
  • Oversee data management for the institutional advancement office including reporting, gift acknowledgements, and accounting


Head of School Support

  • Provide comprehensive and effective support for the Head of School
  • Provide briefings, materials, and recommendations for interactions with specific constituents and donors
  • Collaborate with Head of School to identify, cultivate, and steward strategic outreach partnerships
  • As a member of the senior leadership team, collaborate in developing priorities and strategies for advancing the mission of the School



  • Alignment with Windward’s mission and vision
  • Bachelor’s degree required, master’s degree preferred
  • Proven track record of experience cultivating, soliciting, and stewarding donor relationships with a wide variety of donors
  • Leadership experience in institutional advancement at a nonprofit organization
  • Outstanding written and verbal communication skills
  • Demonstrated strength in internal and external communications
  • Strong interpersonal skills and collaborative working style
  • Ability to build a team and motivate and manage people while also acting as a professional mentor and coach to build the strengths of direct reports
  • Ability to effectively use a variety of computer programs and software; experience with Raiser’s Edge preferred



Exceptional candidates with the skills and experience required to serve as a transformational leader at The Windward School should apply by completing the online application including a cover letter and resume to the attention of, Mr. Jamie Williamson, Head of School. No phone calls please.