The Student Site of Castilleja School


The Student Site of Castilleja School


The Student Site of Castilleja School


‘I’m devastated’: Faculty respond to Head of Upper School stepping down

Sara Flexer
Head of Upper School Anne Rubin stepped down Wednesday

Castilleja Acting Head of School Kathy Layendecker announced on March 26 that Anne Rubin, Head of Upper School, would be stepping down the following day. Rubin’s swift departure comes after Layendecker announced last January that Rubin would leave Castilleja at the end of this school year.

“I am grateful for the school’s support in my request to make this change a little earlier than they had planned,” Rubin wrote in a message to employees. “I believe in the good work of our colleagues and in the potential of our students, and I know that will continue in my absence.”

In July, Rubin will assume her role as Associate Head of the Blake School in Minneapolis, where she previously served as a dean and teacher. She shared that she is stepping down earlier than expected to “shift [her] focus and responsibilities to preparing [her] family to move back to Minneapolis.”

Although Rubin has only been at Castilleja for a little under three years, her impact on the student body, faculty and institution has been undeniable. “I just wish that everybody could have seen all these things that I have grown to know and appreciate about her. I loved every part of who she was,” Colin Quinton, 10th grade chemistry teacher, said.

Rubin first joined Castilleja in July 2021, after serving as Upper School Dean at the Blake School for five years. “She really spent the first semester or two listening. Every space that I observed her, she didn’t put herself at the center of what was going on. She wanted to understand how people thought and how she could support the goals of the school and the students in the best way possible,” Quinton said.

“One thing that I admired as I got to know her presence on campus was that she was the same, no matter who was in the room, whether you were a board member, the Head of School, or a new sixth grader,” Hailey Valdez, fitness teacher and social justice lead, said. “She was going to engage with you in the same way because you were an equally important part of our community. It’s not easy to make everybody feel that way, and I think she did it so effortlessly, which is just phenomenal.”

Throughout Rubin’s time at Castilleja, she has sought to find ways to celebrate students, from journeying across the world with the junior class for Global Investigator Trips to greeting them at the Kellogg entrance during morning drop-off.

Quinton often joins Rubin for these drop-offs in the morning, witnessing her warm and joyful demeanor as she welcomes students to school. “She and I share this love of just watching students be students. She greets people in the best way and brings so much energy,” he said.

Valdez joined Rubin on a GIT trip to Indonesia this past year. “Seeing how she was in Indonesia, how she is on campus, at conferences and in all these different spaces, the biggest lesson [from her] was allowing your students to see you as humans first and teachers second,” Valdez said. “That has really allowed me to develop friendships with my students that I don’t think I would otherwise have had. She gave me that permission to be a little bit more myself with the kids.”

Angelica Ortiz Anguiano ’11, art teacher and former 6th grade dean, stressed how grateful she was for Rubin’s leadership. “When I think about my whole Castilleja experience, she was one of the first people to really see me, what I’m capable of and what I deserve, and I will forever be grateful,” Ortiz Anguiano said. “She was rooting for me—continues to root for me—in any ways that I want to grow.”

Quinton shared Ortiz Anguiano’s sentiment of how Rubin’s leadership has the power to bring out new sides of individuals. “She is the first person who helped me see that I might have something different to give. She’s helped me grow even at this late stage in my career,” Quinton said. “As a leader, her goal was to elevate those around her. I felt really supported by her in a way that was authentic.”

As Castilleja has a relatively small student body and faculty in comparison to other institutions, administrators not only have to navigate professional lives but also personal lives. Ortiz Anguiano emphasized her appreciation for how Rubin approaches these conversations, thoughtfully balancing both the professional and personal aspects.

“With navigating conversations, you need to observe who’s in the room, who’s not in the room, who’s talking, who’s not talking,” Ortiz Anguiano said. “She’s a brilliant observer and can bring that to folks’ attention.”

Ortiz Anguiano further explained that Rubin engages with everything through a lens of equity and access. Both on the Circle and beyond, Rubin has shown that DEI work needs to be done every day, not just with students but amongst faculty as well.

“Not only at Castilleja but across the board in independent schools, I feel like a lot of DEI work is done performatively. [Rubin] was really trying to make that a part of the [school’s] culture, which is not easy to do,” Valdez said. “If you have done DEI work before, you know it is super selfless and exhausting work to do. That just speaks volumes—the fact that she was truly in the trenches, showing up every single day, living and breathing this work.”

Valdez added, “I’m hoping that this DEI work truly continues in a productive and meaningful way and that it doesn’t become performative again in the future. It’s really important to make sure that whoever comes in and replaces her is able to put the same level of care and thoughtfulness into conversation surrounding anti-racist competencies and all the other work that we are doing within the DEIJ realm.”

Although the faculty didn’t know the exact reason why Rubin decided to leave Castilleja a few months before she had initially planned, they shared in the belief that she is taking the time to spend with family and prepare for her move across the country.

In response to Rubin’s departure, Quinton said, “I’m devastated. She’s a close friend of mine, and over the past three years, we’ve grown to trust, appreciate and help each other in all the ways that friends do. The end of that will be missed.”

Valdez expressed, “Minnesota is home to her, and I know that she’s excited for this opportunity, so I’m over the moon for her. But she will be missed very, very greatly, both as a boss but also as a friend.”

In an email to Upper School students, Interim Head of School Julia Russell Eells announced that Peter Hatala will join Castilleja as the new Head of Upper School in July. Hatala previously served as Director of Studies at The Webb Schools as well as Director of Curriculum and Innovation at the Emma Willard School in New York.

In the meantime, Rubin’s prior duties will rest on Gabi McColgan (Director of Academic Policy), Karen Strobel (Director of Teacher Support), Eve Kulbieda (Dean of Upper School Students) and Rich Mazzola (Director of Upper School Athletics).

“It’s a big hit. I think that people will chip in the best that they can, but [Rubin] brought a perspective and a set of strengths that are really valuable to the school,” Quinton said. “She is somebody with a deep sense of understanding about what’s best for the school and the students.”

“It’s been a very challenging year. The students, the classes, and the traditions bring us a sort of consistency that we’ll always have. But I am very mindful that [Rubin] was very integrated into students’ lives,” Ortiz Anguiano said. “[Her departure] leaves a lot more up in the air, but it’s going to be difficult.”

Rubin has fostered a sense of warmth and joy within the Castilleja community, through her presence at Upper School meetings and the handwritten birthday cards that she sends to every student. “She is very much somebody who does what she does because of the kids. I hope that whoever replaces her will be able to foster that same sort of environment, but I think we are going to feel the absence of her warmth and kindness,” Valdez said.

When asked what he thought Rubin’s lasting legacy would be, Quinton responded, “The way that she helped so many teachers feel seen on this campus. That to me is the power that continues.”

“Whoever has interacted with her on campus and had the opportunity to receive a smile from her, enjoy a moment of laughter or get a tarot card reading from her will say that she’s just somebody who makes your day get better,” Valdez concluded. “Above all the things that she has implemented from an academic standpoint, that is the big legacy: just making people feel like they belong.”

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About the Contributor
Sara Flexer
Sara Flexer, Editor of Features
Sara Flexer '26 is the Editor of Features for Counterpoint. This is her second year in journalism, and she enjoys playing tennis, forcing people to read her favorite books and making Pinterest boards instead of doing homework. She is obsessed with all things green: matcha, frogs, avocados, tiny cacti, you name it.

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