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Kyle Wilkie-Glass as Interim Head of School

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Photo credit: leadership announcement letter from Board of Trustees Chair Kimberly Smith Spacek ’91

In March 2021, former Head of School Jessica Bagby announced that she would be departing from the Fieldston community after the 2021-2022 school year and that during the upcoming school year she would serve as the Head of School Emeritus. A permanent Head of School will lead the community through the 2022-2023 school year, but in the meantime, Kyle Wilkie-Glass will be the Interim Head of School.

Before beginning his career at Fieldston, Wilkie-Glass held operational roles in higher education. Wilkie-Glass first started working in student life at the Catholic University of America in Washington, D.C. At Catholic University, Wilkie-Glass dealt with grant implementation, sensitive student conduct matters and managed the student center. Wilkie-Glass then went on to serve as the Assistant Vice President for Campus Operations and Planning at Sarah Lawrence College in Bronxville, New York. This role allowed Wilkie-Glass to get involved in many fun and interesting programs that helped steer the direction of the college. Aside from administrative roles, Wilkie-Glass also taught as the Adjunct Professor for Finance and Business at Manhattanville College.

As Wilkie-Glass looked back at his previous jobs, he said: “These positions gave me insight into school and university operations and I am very happy to have an impact on the operational aspects of Fieldston.”

Wilkie-Glass has been working at Fieldston since 2016, making this upcoming school year his sixth year as a member of the Fieldston community. During his time at Fieldston, Wilkie-Glass was the Chief Operating officer for two years, the Interim Chief Financial Officer for one year and was the Associate Head of School for two years. In addition to these roles, Wilkie-Glass has also overseen the COVID-19 Task Force, Tate Library renovation, creation of the Design Studios and Student Commons renovation. So far, Wilkie-Glass’s favorite responsibility was working with the faculty committee to plan the renovation of the library.

When asked about overseeing the renovation of the library, Wilkie-Glass replied: “I deeply enjoyed leading this project not only because it resulted in a beautiful and functional building, but also because I was able to understand how students use the library at Fieldston. The main floor is a real collaborative space, which you will not find in your typical library. Being able to understand the library gave me a nice taste of what committee work would be like at Fieldston. It was also a bonus that the renovation was ahead of schedule and under budget!”

Wilkie-Glass was interested in working at Fieldston because of the many opportunities that Fieldston provides its staff. Wilkie-Glass identifies himself as someone who can easily get bored and from right off the bat Wilkie-Glass knew that he would never be bored at Fieldston. This statement has remained true to this day, as Wilkie-Glass views Fieldston as a place that has many interesting and exciting things happening at once and plenty of work to be done each day. All around, Wilkie-Glass is happy at Fieldston because he thoroughly enjoys working with the various members of the Fieldston community on a daily basis.

Wilkie-Glass said: “Fieldston is a rewarding place to be involved in and a wonderful place to have the opportunity to lead. Fieldston is also a very complex place, so in my role I really need to be able to solve problems. I want to nurture a school environment where students are succeeding every day.”

Wilkie-Glass was selected for the Interim Head of School position because he previously had worked closely with Bagby. Before coming to Fieldston, Wilkie-Glass consistently engaged with presidents and vice presidents of many colleges as well. The Head of School interacts with all of the Fieldston constituencies including students, faculty, staff, alumni, parents, trustees and neighbors and friends of the school. Wilkie-Glass oversees all of the divisions of the school and is here to deal with problems relating to anything from scheduling issues to questions about bussing. Additionally, the Head of School manages the administrative council which is composed of the principals of all four schools, Head of School Emerita, Director of Finance, Director of Communications, Director of Technology, Director of Enrollment Management, Director of Human Resources, Director of Community and Inclusion, Director of Athletics and Chief Philanthropy Officer. The Head of School’s role is different from the Head of School Emerita’s role in the sense that the Head of School Emerita Jessica Bagby only works with the Board of Trustees to focus on long-term work and the search for a permanent Head of School. This split leadership ensures that the Fieldston community experiences a seamless transition to a new Head of School in the fall of 2022.

Wilkie-Glass has six pressing goals that he wants to achieve during the course of the 2021-2022 school year:

  1. “Safely open and operate the School during the global COVID-19 pandemic.
  2. Conduct assessment of enrollment and recruitment efforts and craft a five-year model with consideration for demand and market factors.
  3. Conduct assessment of the school-wide capital program for deferred maintenance and craft a strategy for the staged execution of the Ethical Culture renovation.
  4. Steward change management within the school community to transition to a new Head of School in July 2022 and organize administrative functions in an efficient, organizationally appropriate manner.
  5. Assess student support efforts and craft a two-year strategy to augment professionals in counselor/psychologist roles, learning center roles and other student support roles. 
  6. Conduct preliminary needs assessment and prepare for a strategic planning process.”

Wilkie-Glass is honored to serve as the Interim Head of School, however he did not apply to become the long-term Head of School. He made the decision to return to his previous position next year because he highly values time with his family and wants to begin doctoral work to learn more about education leadership, more specifically how he could be of use at Fieldston. Wilkie-Glass loves managing school operations and also has a great interest in teaching at Fieldston in the future. He will continue to prioritize his time around his family and current responsibilities at Fieldston, but in the future he would like to get some time teaching in the classroom.

As a final note to the school, Wilkie-Glass said: “This is a place that is very special to me and I know how special it is to all members of our community. I am really looking forward to being a good steward of the school this year. I welcome and invite people to reach out and I can’t wait to see people around campus.”

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