Windward Alumni
There are many ways to stay connected as a Windward alumni, ranging from cultivating professional connections, to volunteering as a speaker at an event, to connecting with old friends and prior teachers at one of the School’s annual alumni events. Are you a Windward alum and want to share an update?
Staying connected
About Our Programs
Windward loves highlighting its incredible alumni, whether it’s inviting them to engage with the community, spotlighting them with updates and articles in our community magazine, The Compass, or welcoming them to inspire our middle school students through Dream Big. The Windward School provides value to alumni through various initiatives, groups, opportunities, and events throughout each school year. Windward alumni participate in networking opportunities, are invited to speak on panels and at lectures, mentor current students, and connect with peers at Homecoming, senior night, and the Windward Fund alumni fundraiser. Read on to learn more about programs designed specifically for alumni of The Windward School.
Your Dreams Are Your Future
Dream Big
Brought to you annually by the Windward Parents Association and Windward Alumni Office, Dream Big: Your Dreams Are Your Future program began in 2011. Each year Dream Big features prominent, inspirational speakers who share their stories about overcoming obstacles and going on to achieve their dreams. The goal of the program is to engage Windward middle school students and our extended community in an encouraging, interactive event as a reminder that having a language-based learning disability need not hold anyone back from a lifetime of achievement.
2025 Featured Speaker
Skylar Handler '14
Skylar is a Lead Creator at VaynerMedia, where she has spent the last four years working at the intersection of content creation, storytelling, brand strategy, and digital innovation. She works with today’s top brands to develop highly effective and culturally resonant social content, driving over 2M+ follower growth and creating hundreds of viral videos that surpass 1M views. Skylar leads social media campaigns with celebrity talent and pioneers platform-first strategies that help brands engage their audiences in today’s ever-evolving digital landscape.
If you are interested in becoming a Dream Big presenter, please email us at alumni@thewindwardschool.org
Questions? Reach out to alumni@thewindwardschool.org