“Commitment to inspiring and sustaining a culture of excellence,” “intellectual nimbleness,” and “long-term success as a strategic thinker” were some qualifications listed in the nine-page Upper School (US) Director job description. After a five-month-long search process, Head of School Jen Price announced Dana Hall School Director of the US Jessica Keimowitz as the next US Director and Science Teacher Michael Chapman as the first US Dean of Teaching and Learning on January 31.

Having served as a teacher, a college counselor, and now a sectional director, Ms. Keimowitz brings experience from a multitude of perspectives, Dr. Price said.

“Ms. Keimowitz brings a bevy of experience,” she said. “She brings a steady, thoughtful presence. She brings a strong commitment to Diversity, Equity, and Inclusion. She brings a strong track record of working well with faculty and staff and having strong relationships with students. She understands the complexity of running an upper school and both the small decisions and the big decisions that have to be made in order to do that effectively.”

The school created the new US Dean of Teaching and Learning position so that Mr. Chapman could further explore his passion for teaching and learning, Dr. Price said.

“Mr. Chapman has an incredibly bright future as an administrator and as a leader,” she said. “Throughout his interview process, he was amazing in talking about the teaching, the faculty experience, and the student experience around learning. I think this is a great match for his skill set, his passion, and where he is in his career.”

Dr. Price, after input from the US Director Search Committee, parents, students, and faculty, made this final decision. Before the announcement, Dr. Price had said she hoped her interactions with the next US Director would have a personal level and a professional level.

“I’m very much of a relational leader,” she said. “It is my hope that we’ll be able to build a caring and trusting relationship where whoever comes in will know that I am there to support them professionally as they navigate this really big job and the impact that’s having on them personally. But that will take some time.”

From the initial US Director job description, Dr. Price highlighted the qualification of “a sense of joy for this important, life-changing work.”

“It’s hard work. It’s important for our community,” she said. “We have to enjoy it because if we don’t, we’re going to burn out, and we have to have an opportunity to take some perspective and even laugh about some of the challenges that we face.”

Five months before this decision, Educator’s Ally, an administrator placement agency chosen to facilitate the hiring process, created the US Director job description with Director of Communications Joe Clifford and Human Resources Director Tamah Rosker. After its posting in October 2021, over 130 candidates internationally submitted a resume and a cover letter by the November 19 application deadline.

Educator’s Ally then moved forward around 20 candidates to the US Director Search Committee, composed of eight Senior Leadership Team members, four teachers, three students, and one parent.

Chief Learning Officer and Search Committee Member Jed Lippard said the Search Committee’s representation created a “kaleidoscope of perspectives” and their discussions excited him.

“We’re still living under the cloud of COVID, and this can take a toll on morale. Therefore being energized by the future and thinking of the possibilities of where we want to be during the search for a leader brings a sense of hope and excitement.”

Director of College Counseling Amy Selinger said the committee offered her a new perspective on her job.

“I was reminded about how interesting and dynamic the students are here, about the faculty and how committed these adults are, and how proud I am of the work that the students and the adults do together. It’s a cool lens through which to see an institution when you’re showing it off to somebody who might come join the community. It has reminded me that I enjoy being here.”

Prior to whittling down the candidates to 12 semifinalists, the search committee did an asynchronous anti-bias training organized by the Diversity, Equity, Inclusion, and Global Education (DEIG) Office to help inform their decision making. US Ceramics Teacher Christian Tonsgard valued the concrete experiences the candidates had in addressing racism at their respective schools, he said.

“We as a school talk about being antiracist; we talk about our DEIG mission. But what’s really important to me is that we stop talking and that we have a candidate who is going to do it, not just to talk to us about these things.” Alisa Ishii ’23, one of three student representatives on the committee, said she saw taking action and challenging norms as important goals for the new US Director.

“I want to see someone who’s really ready to change the status quo of high school education,” she said. “Whether that means something extreme like getting rid of grades and going to a competency-based grading system or no exams, I don’t know. But I just want someone who’s willing to look at those options, and maybe consider that what we’ve been doing up until now isn’t
necessarily the best system.”

Across three days, the search committee conducted four interviews over Zoom with each interview lasting 45 minutes, followed by 15 minutes to review the candidate during which the committee discussed how the candidates fit the school’s needs. Using anonymous ranking, the committee chose five finalists—Greenwich Academy Director of Enrollment and Financial Aid Nina Hanlon, St. Mark’s School Director of Community and Equity John Daves, Mr. Chapman, The Branson School Director of Studies Chance Sims, and Ms. Keimowitz.

Each of the five finalists visited the school for a day to interact with the community in a series of meetings. Their days began at 7:30 a.m. with a meeting with the search committee after which student tour guides showed the candidates around the school. Throughout the day, the candidates met with parents, student leaders, department heads and grade deans, teachers, and students in separate meetings.

The candidates also met with Lower School Director Anthony Reppucci, Middle School Director Mary Dolbear, US Assistant Director Katrina Fuller, and Dean of Students Rory Morton ’81, with whom the US Director works closely. Prior to their visits, the candidates received a school feedback survey of outgoing seniors to assess how they might interpret and act on the results as US Director. At the end of the day, the candidates met with Dr. Lippard and Head of School Jen Price.

Student Council Representative Daniel Wang ’22, who attended Ms. Hanlon’s and Mr. Chapman’s student forum and student leaders forum, said he hoped the US Director would connect with students in a direct manner.

“I have no doubts on the qualifications of all of these candidates,” he said on January 9. “I believe they’re incredibly capable and would learn very fast. However, I’m worried about how attuned they will actually be to students. I want my US Director to speak not in whatever lingo or language that is prevalent in professional development but to really talk in a language that’s straightforward and that students would understand.”

During her January 11 visit, Ms. Keimowitz addressed school innovation, mental health, and the schedule during the student forum. In the student forum, Ms. Keimowitz emphasized the importance of strong relationships between adults and students.

“We think of time as a valuable resource, and how schools use that time says a lot about the school’s priorities. In most schools, more time needs to be spent on creating authentic connections between the students and the adults.”

On Saturday, January 15, Mr. Chapman and Ms. Keimowitz met over Zoom to look toward their tenures together. Ms. Keimowitz said she is “eager, energized, and enthusiastic” for her new role and that she found Mr. Chapman’s dedication to his work and experience admirable.

“He’s a very thoughtful practitioner of teaching and learning. To have someone whose job will be dedicated to that work is incredibly exciting. It will give both of us the opportunity to think about different ways to innovate, different ways to engage the community, and ultimately figure out the best way to serve the students.”

Mr. Chapman, after hearing Dr. Price’s proposition of the role of US Dean of Teaching and Learning, felt a click between his passion and his new position, he said.

“Dr. Price knew my passion was in teaching and in learning: the idea of thinking about how we think about class curriculums; how we structure our classes’ assessments and feedback; how DEIG shows up across all different curriculums. She proposed the idea of this position. I thought, ‘This sounds about right.’”

Mr. Chapman said he is thinking about questions concerning pedagogy. “What do the practices of meaningful teaching look like in the classrooms? What is the process of deeper learning like in the classrooms? What themes and skills are we starting to see that we can build upon as a student goes through each grade within the Upper School, and how do we make those more visible?”

Ms. Keimowitz and Mr. Chapman will officially transition to their roles on July 1, 2022.