Derek Pierce has been the principal of Casco Bay High School in Portland since it opened in 2005. Pierce announced this week that he is leaving at the end of the school year. Gregory Rec/Staff Photographer

Casco Bay High School’s beloved principal is leaving the campus he shaped during 19 years at the helm. He announced his departure to teachers last week, and to the community via email on Monday.

Derek Pierce and Casco Bay are somewhat indistinguishable – he is its first and only principal, and the community-focused school was born of a vision he shared with an adventurous crew of founding educators.

Pierce, 57, said his choice to leave did not come easily.

“It’s a wrenching decision because I love it here,” he said Friday. “I could not feel more fortunate to have been part of this community as long as I have and see it evolve. But it felt like the time was right for me and the school.”

Pierce plans to leave at the end of this school year. Until then, he will do what he can to support the school’s transition to a new principal, he said in a letter to the community. He said he does not know precisely what is next for him, but he plans to keep working and be a booster for education.

“I’m trying to be open to lots of possibilities,” he said.


The district has been fortunate to have Pierce for 19 years, Superintendent Ryan Scallon said.

“Derek has done a phenomenal job working with the staff, the families and the district as a whole to build a great school that people love to have in the district,” Scallon said.

Scallon does not yet have a timeline for the search process. The first step is to take time to celebrate Pierce and then begin searching for the school’s next leader, he said.


It was almost two decades ago that Pierce and the school’s other founders opened Casco Bay’s doors to 75 ninth grade students. Since then, the school has expanded to serve 100 students per grade and has educated almost 2,000 students.

The school uses an expeditionary learning model, which centers on curiosity, autonomy and service. Students learn core subjects, but they also can direct their own education and dive into topics they find most interesting. One of expeditionary learning’s main goals is for students to discover what they can achieve.


Watching students grow and realize their goals is one of the elements Pierce loves most about being an educator.

“What’s so exciting about working with kids in schools is to see them transform in real time,” he said. “To over four years see them expand their sense of what is possible for themselves and gain clarity about what they care about and act on that, that is a real privilege to witness.”

Maggie Ruff, who graduated in 2016, definitely wasn’t expecting to get an email from Pierce seven years after she graduated congratulating her on her successful, young career as a teacher. But she wasn’t surprised, either.

Ruff, now a second grade teacher at Hollis elementary school, was featured in a Portland Press Herald article last fall about young educators who are passionate about the field despite its challenges.

Pierce read the article, emailed Ruff and shared it with Casco Bay’s teachers. She said the effort Pierce made to reach out meant a lot to her.

“It made me feel really valued and even more appreciative of Casco Bay,” she said. “I feel like he really cares so much about the kids who have been part of that school.”


Ruff has nothing but good things to say about Casco Bay and her high school experience. 

The school helped her to grow as a person, think about the positive and be grateful for what she has, think critically, learn independently, create strong relationships with people and make people feel valued, she said.

“It helped me become a good person,” she said.


Pierce was integral in creating that positive environment, said Susan McCray, an English teacher at Casco Bay who, like Pierce, has been there since the start.

“The greatest gift of Derek Pierce is that he believes in the possibility and potential of every human to be great, to do tremendous things and to transform,” she said.


“He created the atmosphere, the environment, the structures and the human connections for that to happen.”

McCray said she cried when she heard he was going to leave the school because she’s so grateful for what he’s done – the school he created and the doors he’s opened for students and staff.

“I wouldn’t have this reaction if he was just a supreme leader,” she said. “It’s because we all made it together and it’s an opportunity to step back and look at how far we’ve come.”

Pierce said he doesn’t exactly want to leave Casco Bay; he loves working with the students and teachers and being in Portland. But said he feels like he’s run his course and that it’s time for him to create space for new leaders and new perspectives that will ensure the school continues to evolve and innovate.

“It’s super hard to leave something you love. I may never have a job that is as fulfilling, as important, as meaningful as what I have now,” Pierce said.

“But I knew it had to happen and the school is in an excellent place right now and it feels like the timing is right. It’s ready for new leadership.”

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