Activities director Cunningham takes on new administrative role

Cunningham dancing in the Teacher Quad Day during Homecoming Week in 2022.

Though Cunningham was originally going to move north with her family and leave the school, she stayed after being hired as the fourth assistant principal in addition to her prior role as activities director and leadership teacher.

When Kristen Cunningham went home for summer break on June 8, she was prepared to never return to Saratoga High. Having worked as the activities director and leadership class teacher for the past two years, she planned to sign on as an assistant principal at a middle school in Loomis, Calif., a city north of Sacramento where her family was planning on moving over summer to support her aging father-in-law. They had already bought a home and were prepared to leave Saratoga.

However, in an unexpected turn of events, she found herself interviewing for a newly opened part-time assistant principal position at the school later that month. Former assistant principal Brian Thompson, who was a full-time administrator, left the district at the end of the school year.

When Cunningham’s family had decided not to move for a multitude of reasons, she found herself slightly relieved.

“I love my job here, and I love what I do,” she said. “I love the students, I love the community. If anything, it was making me so sad to leave my job here. I was kind of actually a little bit excited, honestly, about being able to stay. It was hard for me to tell the other school, but at the end of the day, maybe that opened up a spot up there for somebody that really needed a job, so I feel like things happen for a reason.”

Cunningham’s family decided to keep their home in Loomis, allowing them the flexibility to visit as frequently as they want.

Long before her family had begun considering their move, Cunningham always knew she wanted to eventually move into administration. In August 2022, she earned an administrative credential from San Diego State University.

“I knew at some point, I was going to want to pursue an administrator position, but I was just waiting for the right opportunity to come up,” Cunningham said.

Cunningham began working at the school in 2021 as the activities director and leadership class teacher. This role was a 0.8 FTE (full time equivalent) job, meaning roughly 80% of her work time was spent in these roles. She spent the remaining 20% teaching students in the Edgenuity program who were still learning from home in the 2021-22 school year. In the 2022-23 school year, she maintained her activities director and leadership teacher positions while teaching two strategic learning classes at Los Gatos High School.

When Cunningham heard about the opening as an assistant principal, she said that she found the role quite appealing. The school was offering her a 0.6 FTE activities director and leadership teacher and a 0.4 FTE administrator position, requiring that she interview for the role alongside other outside candidates.

“I was really excited because I love Activities and Leadership and the fact that I didn’t have to leave those was really a draw for me, but it would also allow me to get my feet wet in administration,” Cunningham said.

Cunningham previously worked at Valley Christian Junior High School for eight years as the Student Support Services Director. Though not an official administrative position, she found herself gaining invaluable experience which has already helped in her official role.

Despite this unofficial experience working in administration, Cunningham recognizes the steep learning curve she will have to overcome during her first year as assistant principal. The district is supporting her in pursuing a 2-year “Call Clear Program,” in which an administrator can earn a credential after working with a one-on-one coach twice each month.

By holding two simultaneous roles, Cunningham foresees time management as being her biggest challenge. For example, she spent 70 hours total on campus during Homecoming week last year. Now, in addition to taxing weeks like that, she is occupied with administrative tasks such as overseeing the Visual Performing Arts and World Language departments. While she gets acquainted with her new role, she is relying on her fellow administrators — principal Greg Louie and full-time assistant principals Abra Evanoff and Matt Torrens — to help her ease the load as needed.

As she finds her footing balancing a new role with her ongoing commitment to the leadership program, Cunningham looks forward to how she can learn and grow in her first year.

“I want the staff, the community and our administrative team to feel like I am putting in the work and learning and growing as an administrator because I am so new to it,” she said. “On the activities side, I just want to continue to be a light in the class. For my leadership students, bringing community and fun to the school is so incredibly important. My goal is to create that environment here and balance the roles the best that I can.”