Dr. Gleason announces he will step down at the end of the 2022-2023 school year


After four years at KO, Head of the Upper School Dan Gleason announced that he will be stepping down from his role at the end of the 2022-23 school year. Dr. Gleason has held the role of Head of the Upper School since 2019 when he arrived at KO, and in his time here he has also taught English classes and been an advisor to freshmen and sophomores.

In his role, Dr. Gleason oversees all changes to the curriculum and the Upper School teachers. Interim Dean of Students Kata Baker has had the pleasure of working with Dr. Gleason very closely this year. Mrs. Baker, who manages student life, says her work often intersects with Dr. Gleason and the two collaborate closely on planning any upcoming programs, such as field trips and special events. In their work together, Mrs. Baker has noticed Dr. Gleason’s incredible thoughtfulness when approaching any issue. “He has this amazing ability to look at an issue from every single angle,” she said. “He’s very aware of the people in the community.”

One of Mrs. Baker’s favorite memories with Dr. Gleason is from this summer when they both attended a professional development conference. They shared a five-hour car ride home from Philadelphia, and Mrs. Baker admitted that there was never a quiet moment in the car. She enjoyed getting to know Dr. Gleason better and learning more about his passions. 

Head of School Tom Dillow is thankful for Dr. Gleason’s contributions to making KO a better place for students and faculty. “He is a genuine scholar and thoughtful about innovation in curriculum,” he said. “He has been a wonderful leader to bring about initiatives in the Upper School that align us a little more with our strategic plan.” 

Some students on campus have had the opportunity to know Dr. Gleason as an English teacher as well. Dr. Gleason has taught two English electives: Know Yourself (a senior thesis elective combining literature and psychology) and a fall elective focused on climate change and literature. Senior Emily Evans is taking the climate change elective this fall and has appreciated Dr. Gleason’s passion for his students and the subject matter. “He is very passionate about what he teaches and ensures that his students are comfortable in what they are studying and in the class environment,” she said. 

Dr. Gleason has also served as an advisor for freshman and sophomore students, helping them adjust to the Upper School. Sophomore Lily Temkin who has had Dr. Gleason as her advisor for the past two years is grateful for his constant encouragement and support. “He would always encourage us to pursue passions of ours whether it be in school or out of school, and no matter what, he always wants us to succeed,” she said. 

Lily appreciates the fun environment Dr. Gleason creates in advisee group. “A few weeks ago he realized that he never took pictures of us last year, so now at the most random time he’ll pull out his camera and have us pose,” she said.

Like many others, the Covid-19 pandemic allowed Dr. Gleason to step back and think more about his work-life balance. He came to the conclusion that he wanted to find a job that would work better for his family. “My kids are turning nine this year, and I think they really want to be around me right now, and they’re not gonna want to be around me that much longer,” he joked. 

Dr. Gleason shared that the hardest part about leaving is the relationships he has formed. “What makes leaving so bittersweet is the people here are just wonderful,” he said. Some of Dr. Gleason’s favorite times at KO have been spent at sports games, concerts, musicals, and other special events. One of his favorite memories was the class of 2021’s senior prank in which all of Dr. Gleason’s office was put out on the senior green. 

Although Dr. Gleason is unsure of what he will do next, he is looking forward to spending more time with his family. “I’ll be using a lot of the skills and experiences that I’ve learned here at my next job,” he said.

The KO community will certainly miss Dr. Gleason and we wish him the best of luck in his future endeavors!