She didn’t know it at the time, but when Courtney Rowley was a senior at Wayland High School her work with Claypit Elementary students would be her calling in life.
Now, after two short years in Wayland schools, she is taking over as interim principal at Wayland Middle School.
In a recent memo, Dr. David Fleishman announced that Rowley will transition from her role as assistant principal to the role of interim principal during the upcoming 2026-27 academic year because Principal Deborah Romeo stepped down due to medical reasons.
Rowley, a native of Wayland and a Claypit alum, originally set out to be an attorney. But, as she pursued her studies at NYU, she quickly discovered that she was drawn to helping out in schools the same way she had as a WHS senior. During her freshman and sophomore years in college she volunteered to help in schools in NYC. By her junior year, she knew that she was hooked so she started a minor in education.
“I was inspired to go into education when I was in high school,” said Rowley. “My family became a foster family. I witnessed first-hand the immense impact that early literacy and educational opportunities had on my foster siblings and their families. This experience inspired me to become passionate about all kids having access to a high quality education.”
Rowley will collaborate with former Claypit and Happy Hollow Assistant Principal Rachel Scott and Special Education Administrator. Rebecca Speicher. Dr. Fleishman feels that this will be a highly successful administrative team.
“We feel confident that Courtney, Rachel, and Becca will be a strong and cohesive team that will support students, families and staff. They will be available throughout the summer working to ensure that the transition is seamless,” Fleishman said in his correspondence to the community.
Before returning to Wayland two years ago, Rowley’s educational career in New York included an array of accomplishments. She taught social studies for over 13 years; was part of the founding staff at two schools, where she also served as a teacher-leader; created a Civics curriculum and taught college-like classes where students researched a subject they were passionate about and then traveled to Washington, D.C., to lobby for these issues.
Rowley is excited to step into her new role this year and build on the strengths and promising practices in place to support the school community. She fondly remembers her own teachers in the district, specifically the ones who shaped her love for history and law, such as Erin Lehmann and her enthusiasm for U.S. history, David Schmirer and his incredible knowledge of politics, Joseph McCoy who brought history to life, and Kevin Delaney, whose mock trial is what inspired her to consider going into law. Rowley hopes to add her own flair to the school’s community.
“I see the role of a leader as uplifting your team by elevating and empowering others to take on new challenges and champion the success of my colleagues,” she said. “For example, I am looking forward to bringing Student Government back and exploring additional ways in which student, family and teachers voices and ideas can be heard and actualized for the greater good of our community.”
When she’s not in school Rowley enjoys spending time in the kitchen with her husband creating new dishes, swimming, playing board games and dolls with her daughters, and hanging out and taking walks with their rescue dog Jenny.



