Kimberly Cawkwell, M.Ed.

Kimberly Tsai Cawkwell, M.Ed. has served over thirteen years in the education ecosystem. As the Director of Programs at Challenge Success, Kimberly is honored to be in community with others to advocate for equitable systems and practices that nurture wellbeing, belonging and engagement for all. In addition to her work at Challenge Success, Kimberly currently serves as an Educational Advisor at the High Tech High (HTH) Graduate School of Education; supporting M.Ed students in developing culturally sustaining/responsive pedagogy in their school spaces. Growing up as a multilingual learner in a semi-isolated motel next to a busy New Orleans expressway, living through the duality of American and Taiwanese cultures, and experiencing teaching and learning in variety of settings around the globe, Kimberly has developed a unique lens for culturally responsive environments and an insatiable desire to center student voices in classrooms. Through the opportunities to learn from students in her own classrooms to students from diverse corners of our globe, Kimberly believes deeply in student-driven transformative learning that sparks a common love and joy to seek knowledge. As she continues to support systemic change that lifts up student voices and honors the passions and identities of all students, Kim is grateful for the invaluable knowledge gained from others, holds humility as a practitioner and mentor for Deeper Learning practices, and is continuously inspired by the beautiful humans who are called to serve youth.
Prior to joining CS, Kim was a founder of two High Tech Elementary (HTe) project-based learning schools, a former coach and design specialist at the University of San Diego, New Tech Network, and Center for Love & Justice.. She holds a B.A. from the University of California, Riverside and M.Ed and multiple-subjects credential from the University of California, San Diego. When she’s not designing and facilitating learning, Kim might be found spending quality time with her two daughters, loving spouse, and family in Oceanside, San Gabriel, and Taichung. Her core values are family, joy, and equity.