Celebrating Barb Drayer’s Legacy to The Windward School After 12 Years of Service

Stephanie Huie

Director of Development

Ms. Drayer is pictured on the left with alumni parent and former Windward Parents Association President Leslie Breck. 

It wouldn’t be surprising to those who know her to hear that most of the contacts in Barb Drayer’s personal phone are Windward-connected in some way. As director of development, Barb forged strong, long-term bonds with donors, trustees, and parents, many of whom still count her as a friend. “Building relationships is my favorite part of the job,” she shared. “[While at Windward,] I also oversaw the Windward Parents Association (WPA), so that was really fun. The relationships I made have been truly special. There are former trustees and alumni parents who I still go out with.”  

One close friend, Ellen Bowman, President of the Board of the Trustees, shared many praises for Barb’s natural skill at relationship-building. She said, “Barb’s devotion and passion for The Windward School will be eternally missed. She has this ability to make everyone she meets feel comfortable and at ease because she connects us as one Windward family. Her care for all Windward families is evident, and Barb has always ensured that every family really enjoys our incredible program at Windward.” 

Ms. Drayer’s impact during her 12-year tenure at Windward has been far reaching, extending as far as the name itself. When she joined the team in 2007, the name of the school was Windward School. She explained, “There was a Windward School in Los Angeles, and the two schools often got confused. Plus, the LA school has a completely different mission.” Barb suggested the name The Windward School to help differentiate the two, and it stuck. That example highlights the leadership style that not only grew the annual fund by 120%, but also successfully managed a $25 million capital campaign for the NYC campus, among other initiatives. 

In fact, some of these initiatives have now become an integral part of Windward, with others growing into annual traditions. During her second year at Windward, along with former Head of School Dr. John J. Russell, Barb envisioned a magazine, The Compass, to inform constituents about community happenings. It has become hugely popular and is now a biannual publication. She also introduced the Platinum Circle, which recognizes faculty and staff with 20+ years of service. Each May, both current and former long-term employees gather for a dinner to celebrate each other. “It’s so fun to have what I call the ‘founding mothers’ there as well as current employees, some of whom have been here for two decades, four decades,” Barb noted. “It’s such a hoot – you hear the old stories and all the laughter. It’s one of my favorite nights each year.”  

Ms. Drayer has been a frequent presenter at both the NYSAIS and NAIS conferences, covering topics such as supporting advancement goals throughout a leadership transition and guidance for development professionals after receiving a major gift. Post-Windward, Barb intends to fundraise for small- and mid-sized organizations through her firm Drayer Scott Consulting. 

Moving forward, the director of development for The Windward School will be Angel Francis, who brings over 14 years of development experience, most recently as Director of Major Philanthropy at St. Francis College in Brooklyn.