Head of Upper School Cindy Trask to leave Westminster


Courtesy Cindy Trask

After five years at Westminster, head of the Upper School Cindy Trask is moving on to be head of school at St. Catherine’s School in Richmond, Virginia. As Westminster’s head of Upper School, Trask oversees all aspects of the Upper School, including academics and student life. Trask plays a large leadership role and has accomplished many things in her career at Westminster.

“I’m grateful for the team that has developed in the Upper School, and I think that has really grown to do incredible things” said Trask. “We’ve started a student advisory council, we’ve talked a lot about student voice over the years, and we have made advisements coed. These accomplishments I am really happy about. But I always feel that nothing is ever finished, and every good question leads to another good question.”  

Before coming to Westminster, Trask graduated with honors from Dalhousie University with a BA in biology and mathematics and has a B.Ed. from St. Mary’s University and an MA in educational leadership from the University of Richmond. Trask taught AP biology and chemistry and served as the head of the science department at St. Johnsbury Academy in Vermont from 1996 to 2006. Then, in 2006, she taught biology and chemistry for two years at the Collegiate School in Richmond before going to St. Catherine’s School in 2008, where she also served as science department chair. She was named head of Upper School at Westminster in 2016, following the interim head of Upper School and current dean of academics and curriculum Jim Justice. 

“She led the Upper School well, especially during the construction of Hawkins Hall and Campbell, when students had classes in cottages” said Justice. “She has done great in expanding opportunities for students who are interested in innovation, technology, and STEM, which has always been really important to her.”

Westminster alumna Chanley Small, the current Upper School Dean of Academics, will serve as the interim head of Upper School for the 2021-2022 school year.. Small has been at Westminster for 14 years, starting off as in the Upper School science department, teaching biology, anatomy, physiology, scientific research, and statistical analysis. Before coming to Westminster, Small received her PhD from Emory and was a research assistant professor there, researching genetic, reproduction, and environmental epidemiology.  From 2010 to 2017, Small was the science department chair and served as JanTerm coordinator from 2015 to 2018. In 2017, Small was named the academic dean for the Upper School, a position that heads up academic strategic planning processes. 

“Right now, during the spring, Ms. Trask and I are working on the transition together. I am trying to meet with all the Upper School faculty individually to touch base on COVID-19,” said Small. “I’m excited to start.” 

Small plans on meeting with this year’s current eighth graders, who will be in the Upper School next year. 

“They’ll hopefully have a familiar face in the Upper School,” said Small. 

In Richmond, Trask will begin her new job on July 1, 2021, following the 11th head of school Terrie Hale Scheckelhoff. 

“It definitely is going to be different, being that it is an all-girls school, and instead of just being head of Upper School, I will be leading all K-12 divisions,” said Trask. “The students at St. Catherine’s and Westminster definitely voice the same concerns about equity, inclusion, and school safety regarding the coronavirus, and I hope to really make sure that they know that their voices are heard.” 

This desire to increase emphasis on student voices at St. Catherine’s was one of Trask’s original goals when starting in 2016 as head of Upper School at Westminster. 

“We always wanted to make sure that students got to be at the table and voice their thoughts and opinions, because that is what should be valued greatly,” said Trask. “My advice to the high schoolers going forward is to continue to have your voice heard, and to know that students are the most important reason as to why we are at school.”