Dr. Fay’s weekly newsletters are an iconic Upper School institution within themselves, an anticipated window intoWT student life, a constant reminder of how we make each other proud each week, a celebration of growth and learning, and confirmation that the community we chose to become a part of remains a connected, inspired, and kind one. We are after all, “where smart meets heart,” and in talking to peers and faculty about Dr. Fay, it became evident that this maxim aptly describes the Upper School Director herself. 

Those of us who entered the upper school during pandemic learning initially knew her best by these messages of hope, encouragement, and constant progress. “As a parent, I’ve always appreciated the thorough, detailed, and consistent communications,” says Bonnie Thomas, mother of sophomore Ella. The consistency and reassuring nature that mark these reliable reports mirror the expertise and poise with which their author leads. Dr. Fay has born witness to and helped us thrive in tandem with and in spite of the various ebbs and flows the Upper School community and the wider world in which we exist has faced. So it was with great sadness that last month, while finishing their scan of her spirited account of the various performances and student endeavors, Upper School students and families came upon her thoughtfully penned resignation. 

A dedicated faculty member since 2014, and a WT alumnae parent herself, Dr. Fay has watched 6 classes graduate from the upper school in her time here. A Ph.D. in psychology, Has been an administrator at some of Pittsburgh’s finest meccas of higher education including Pitt and CMU.

For all of the education, influence, and high regard in which she is held, Dr. Fay is a refreshingly friendly and approachable figure to even the greenest members of the Upper School (this includes underclassmen chasing her down for an interview). The first time I met her was in the middle school Finkel library, during a question & answer session on freshman year course registration. She handled our never-ending string of redundant, sloppily-posed, irrelevant and droning questions with grace, patience, and compassion. High school can feel intimidating, but Dr. Fay never was; in fact, she made it less so, and her obvious love for her job and the community she works with was infectious.

Always a friendly force, the common denominator in all descriptions of the upper school director is kindness and radiant warmth. It was just a few weeks ago that Dr. Fay found time to join Voices’ very own Nur Turner in a discussion about Halloween for a seasonal article she was writing. 

“As this data collection came to a close I decided to peek through Mrs. Skiba’s office as I saw Dr. Fay and her chatting. I asked them what they were going to dress up as, and they said they will not be participating in Halloween as it’s a Sunday. They told me to ask Mr. Miller, as he always dresses up for Halloween.”

And this September, a very new freshman felt compelled to write about the warmth she was met with the first time she found herself in the upper school office, suffering a migraine.

“So, I sat in the dark of Dr. Fay’s office for what seemed like an hour. This was an unbearable experience, but I was treated with such kindness by people whom I didn’t know. I felt like I was part of a community. I felt like I belonged.”

To Dr. Fay, directing the upper school often means being a student media Halloween costume pundit, defacto school nurse, and champion of scholasticism. 

An indelible part of Dr. Fay’s legacy is her fearless way in which she guided her colleagues, upper schoolers, and their families, through what we can only hope was the toughest epoch of pandemic schooling we will see for a long time. In fact, as fate would have it, Dr, Fay actually served as Director of eLearning at Winchester Thurston for 4 years prior to the pandemic. Her extensive experience and preparedness in this department coupled with courageous adaptability, helped WT retain its hallmark excellence and a strong sense of community, even online, and cemented us as a leading example not only in resilience but in all of the ways that remote learning can go right.

Dr. Andy, who has worked with Dr. Fay for eight of the eleven years, at Winchester Thurston and has worked “Dr. Fay is a scholar and academic whose intellectual mind is unmatched at WT.  In my career as a university professor in the UK and US, and here at WT, I have not met an intellectual match that rivals Dr. Fay. As a leader, she has always put students and student learning first and foremost. WT is losing a leader whose academic background in student learning and assessment will sorely be missed.  Personally, I am going to miss our talks from everything from soccer and all things WT to our discussions on philosophy, international affairs, and the state of truth and the fight over facts today. If you have yet to sit down with her, do so before the end of the school year.”

Dr. Fay concluded her statement by saying “It has been a joy and an honor to lead the Upper School, and I thank you all for your support.” But the unanimous opinion that pervades is that the “honor” has been all ours. Thank you Dr. Fay for many great years and for this one, that isn’t over yet.