Faculty and Staff Directory

Windward teachers are experts in their fields, driven to continuously hone their skills. More importantly, they are excited to teach and share their own love of learning with students. Faculty and students enjoy the discoveries of scholarship together in a positive, comfortable classroom environment. These strong relationships promote lasting bonds that are a hallmark of Windward’s learning community.

Please use the directory below to view faculty information, photos, biographies, and honors.
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Jocelyn Castillo

Jocelyn Castillo

Titles: Coordinator to the Collegiate Division
Candice Chiang

Candice Chiang

Titles: World Language Teacher
Sarah Clark

Sarah Clark

Titles: Director of the Center for Teaching and Learning
Tammy Clem

Tammy Clem

Titles: Director of Counseling Services: Middle School; Associate Director of DEIB: Faculty Recruitment and S, Associate Director of DEIB: Faculty Recruitment and Services
Julia Coley

Julia Coley

Titles: Assistant Head of School, Director of Prep Division
Carrie Creighton

Carrie Creighton

Titles: World Language Teacher, Coordinator of Global Trips & Activities
Jennifer Dao

Jennifer Dao

Titles: Assistant to the Head of School / Admissions Coordinator
Emily Dawe

Emily Dawe

Titles: Associate Director of Middle School, Math Teacher
Michael Day

Michael Day

Titles: Instrumental Music Lead
Tony de Los Reyes

Tony de Los Reyes

Titles: Visual & Media Arts Teacher
Paola DeCastro

Paola DeCastro

Titles: World Language Teacher, Chair
Christina Dempsey

Christina Dempsey

Titles: Performing Arts Teacher (Dance), Athletics Teacher, Cheer Program Lead
Bruce Eskovitz

Bruce Eskovitz

Titles: Performing Arts Teacher (Instrumental Music)