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Chief Advancement Officer

Chief Advancement Officer

The Windward SchoolCity of White Plains, NY, United States
2 days ago
Job type
  • Full-time
Job description

Institution Overview

The Windward School offers children with language-based learning disabilities and their families a proven path forward when they need it most.

Windward’s goal is to remediate language-based learning disabilities. This goal is achieved through proven, evidence-based, multisensory academic programs, combined with the dedication of expertly trained teachers. For decades, the School has helped children achieve reading and writing proficiency so they can transition seamlessly back into mainstream schools. The level of support and specialized education provided at The Windward School is unparalleled, offering families opportunities and guidance that they simply won’t find anywhere else.

The Windward School focuses on more than just literacy, giving students the foundation they need to become well-rounded, confident individuals. The strong academic program is complemented by music, visual arts, drama, field trips, social events, and a broad range of extracurricular activities that provide opportunities for exploration, community building, personal growth, and emotional intelligence. Windward’s successful alumni are a testament to how the School makes a lasting impact on the lives of students and their families.

Windward believes in forming true partnerships between administration, families, and teachers to create the best possible outcome for its students.

Windward benefits from the support and expertise of The Windward Institute, which helps sustain a strong research focus and ensures access to high-quality professional learning opportunities across the community.

A Window Into Windward :

  • 4 Divisions – 3 campuses – 1 School
  • Grades 1-9
  • 98% of students successfully return to mainstream schools
  • 95 school districts served by the Windward School
  • 1-in-5 Windward students receive financial aid
  • 11k professional development hours given to teachers per year

Position Summary

The Windward School seeks a talented Chief Advancement Officer (CAO) to work closely with the Head of School (HoS), Board of Trustees, and executive leadership team to help lead Windward through a period of growth and development. The CAO is responsible for advancing Windward’s life-changing mission by securing diversified, sustained support for the School and The Windward Institute. They will build and maintain strong relationships both internally and externally, identifying and seizing upon new opportunities, and ensuring effective communication with donors, trustees, and the wider community.

The CAO is responsible for all development, alumni relations, marketing, and communications initiatives while serving as Windward’s lead fundraiser and advancement strategist, overseeing an approximately 20-person staff (including the Director of Development, Director of Marketing and Communications, and Advancement Chief of Staff, each of whom is a direct report). The CAO reports to the HoS, serving as an important thought partner thereof as well as a member of Windward’s Executive Cabinet and the Senior Leadership Team. This leader will be an active part of the Windward community and prioritize meeting with families, strategically building long‑term relationships and investment (prioritizing genuine connections versus short‑term transactions) while instilling an institution‑wide culture of philanthropy. Increased philanthropic support to

Windward is critical to fueling financial aid distributions that will be key to achieving sustainable enrollment levels.

The successful candidate will have a strong history of fundraising success, particularly with major and principal gifts, and deep knowledge of advancement best practices. They must possess a gravitas and style compatible with the New York metropolitan area’s philanthropic circles as well as the ability to engage these networks with aplomb. They will be an experienced manager and mentor capable of inspiring and motivating Advancement Department staff, Windward leadership, and volunteers to achieve revenue growth and diversification.

Excellent interpersonal skills and emotional intelligence are a must, and the CAO should have outstanding oral and written communication skills.

Candidate Profile

While The Windward School will consider a broad range of backgrounds, the ideal candidate will have the following qualifications / experience :

  • Alignment with and passion for Windward’s mission and vision.
  • Leadership experience in institutional advancement at a nonprofit organization, with a preference for experience that includes service to an independent school. Broad knowledge of all functional areas comprising a comprehensive advancement program, inclusive of development, alumni relations, and enterprise‑wide marketing and communications.
  • Knowledge of and fundamental adherence to the principles, ethics, and best practices of modern advancement, including the appropriate integration of corresponding programs to enhance knowledge of and engagement with Windward, diversify the funding base, and cultivate greater donor commitments.
  • Demonstrated success in developing the case for support and executing strategic, innovative fundraising plans. Experience in collaborating with executives, senior staff, and board or other volunteer leaders on advancement‑related activities, providing them with quality support and intelligence and increasing their comfort with and success in fundraising. Proven track record cultivating, soliciting, and stewarding donor relationships and evidence of routinely securing six to seven‑figure gifts.
  • Ability to build a team and motivate and manage staff while also acting as a professional mentor and coach to build the strengths of direct reports. Track record of maintaining best practices, clear goals and associated metrics, and shared accountability as well as working cross‑departmentally when necessary to achieve results. Experience managing budgets and revenue forecasts.
  • Demonstrated ability to integrate data into decision‑making and strategy development.
  • Sophisticated knowledge of the players, strategies, and trends in giving within the New York metropolitan area as well as demonstrated fundraising success therein.
  • Outstanding written and verbal communication skills. Demonstrated strength in internal and external communications.
  • Strong interpersonal skills and collaborative working style.
  • Ability to effectively use a variety of computer programs and software, with a preference for experience with Raiser’s Edge.

    • Diversity, Equity, Inclusion & Belonging | Equal Opportunity Employer

    The Windward School is committed to creating and fostering a community that is inclusive for all its members, with an overarching goal for every person to feel a powerful sense of belonging at the School.

    The Windward School provides equal employment opportunities without regard to race, color, national origin, age, sex, religion, disability, marital status, sexual orientation, military service, genetic information, or other categories protected by law.

    Download the full position description via the following link :

    https : / / dsgco.com / search / 22512-windward

    The Windward School has retained the DSG Fundraising & Advancement Practice of DSG Global to assist in this confidential search process. Inquiries, nominations, and applications (current resumes and cover letters) may be submitted via the following link or directed to the leaders of the search team :

    https : / / talent-profile.dsgco.com / search / v2 / 22512

    Gerard F. Cattie, Jr.

    Global Managing Partner and Practice Founder, DSG Fundraising & Advancement

    gcattie@divsearch.com | 212.542.2587

    Ian McCray

    Managing Director, DSG Fundraising & Advancement

    ian.mccray@divsearch.com | 802.989.3764

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    Chief Advancement Officer • City of White Plains, NY, United States