Read The Compass Winter 2022 Issue

Windward teachers' commitment to their students is the heartbeat that makes The Windward School the special place that it is. Every Windward teacher makes an impact, because they not only help their students learn the academic skills and strategies necessary to reach their academic potential, but also guide their students in developing confidence in their abilities.

The Compass Winter 2022 features the stories of five alumni—Matt Bloom ’13, Bianca Rizzo ’10, Derek Kirk ’01, Lexa Krawchick ’14, and Lizza Chapey ’13—who have come full circle and are now teachers at The Windward School. Each alum shares reflections about their time as students and what their experience has been like returning to their former school. Read more as these alumni share how their journey at The Windward School has continued on, first as students and now as teachers. 

This issue also shares Windward's first-ever Diversity, Equity, Inclusion, and Belonging (DEIB) mission and vision statement. As part of the Three-Year Plan for DEIB initiatives, the DivE In Committee, composed of faculty, staff, parents, guardians, and trustees, was tasked with crafting a DEIB mission-vision statement for Windward, which was approved by the board of trustees this fall. 

The faculty/staff spotlight showcases a deeper look at the incredible work that Maintenance Supervisor Juan Jimenez oversees on a daily basis. Find out the five most common requests that Mr. Jimenez hears from his colleagues at the Westchester Lower School. 

Two alumni returned to campus to deliver inspirational speeches to the Windward community. Will Dooley '18 was invited to give the 2021 Commencement address to the graduating eighth-grade students. Reed Switzer '19 was the 2022 Dream Big speaker, and he discussed his post-Windward career as a budding entrepreneur. 

We invite you to browse the entire issue of The Compass Winter 2022 magazine online at You can read the latest magazine issue plus access our archives of letters from the head of schoolfeature stories, faculty and staff spotlights, alumni success stories, and more!