Leadership Profiles

Chris Raymaakers

Profile

Chris was appointed as The Winstedt School Principal in 2022 following nearly 25 years of working in education. Prior to joining Winstedt, he was Deputy Principal at the Singapore American School (SAS).

Chris brings to Winstedt a forward-thinking and innovative approach as an instructional leader in education. He has extensive pedagogical knowledge and strategic insights including 15 years at SAS where he assumed numerous leadership roles and spearheaded key school-wide strategic initiatives. Committed to ongoing school improvement, Chris has served as both a Visiting Committee Member as well as a Visiting Committee Chair with the Western Association of Schools and Colleges (WASC) where he continues to help schools focus on advancing high-quality education. Recently, he has also become a co-researcher with the University of Melbourne on an international scoping study that focuses on the impact of Innovative Learning Environments on student learning, well-being, and inclusion. He has presented and led workshops around Asia on topics such as developing structures to personalise the learning experience for students, positive school discipline practices, and designing innovative learning environments.

Chris began his career in Calgary, Alberta Canada as a middle school math and science teacher, and was the Math Department Head at the Taipei American School in Taiwan.

In addition to his proven track record in educational leadership, Chris has a deep connection to Winstedt. He was a member of Winstedt’s Academic Board from 2019 to 2022 and has been a longstanding member of the Winstedt parent community — his son Ellis has been a Winstedt student since 2014.

Education