Many members of the Fieldston community have been surprised to learn the school has a Chief Executive Officer (CEO). Some might have been made aware of this fact after reading the title of this article. Even so, Kyle Wilkie-Glass has taken on the role with a level of expertise and gusto so immense that he has made the new position a seamless addition to the Fieldston administration.
However, CEO is far from Wilkie-Glass’s first experience as a member of an admin team. At Sarah Lawrence College, he oversaw a host of non-academic sectors of the school before doing the same as a new faculty member at ECFS in 2016. Since then, he has worked to guide the COVID-19 task force, Tate Library renovation and the School Financial Office. When Wilkie-Glass undertook the role of Interim Head of School for the 2021-2022 school year, he centered his leadership around strategy and organization. After all, with a storied list of executive and administrative experiences, it is within Wilkie-Glass’s nature to embrace each new role from a systems-based, intentional perspective.
Recently, I sat down with Wilkie-Glass in his office perched at the top of the 200’s building. As underclassmen lunch commenced, so did a rather intriguing conversation about Wilkie-Glass’s past, present and future at Fieldston, as well as his goals for the institution as Chief Executive Officer.
Our discussion is detailed below.
Saskia Sommer: Chief Executive Officer is a role you’ve taken on relatively recently; can you explain a little bit about what it entails and what your day looks like as Fieldston’s Chief Executive Officer?
Kyle Wilkie-Glass: “Totally. Let me even back up a little bit further. I came to ECFS in 2016, and I came here from Sarah Lawrence College which is not far from here. At Sarah Lawerence, I managed kind of like the kitchen sink of non-academic operations. When I came to ECFS it was a very similar portfolio of services. I started at ECFS as the Chief Operating Officer. A couple of years later, I was the interim Chief Financial Officer for a year and then I was the COO and Assistant Head for Strategic Initiatives. Then, I was the Interim Head of School, and then the Associate Head of School and now I’m the Chief Executive Officer. So, my role has really morphed a lot over time.
There are a lot of different ways that my time at ECFS has been really rewarding and really fulfilling, and that’s [helping where it is needed] one of them. Whenever there has been a need identified at the school or I’ve needed to go in and organize something a little bit differently or think about something a little bit differently, I’ve been given the license to do that. The creative part of my brain loves that, the problem-solving part of my brain loves that and that’s kind of where I’ve spent a lot of my time at the school historically. So, the rule right now as Chief Executive Officer or what I do, again, is that I broadly manage operations at the school.
Some of the things that are reported to me that I work with most closely are things like the school’s finance and investments, human resources and legal affairs. I work with our advancement office –our development office- which does our fundraising; our communications office; alumni relations and events; facilities; campus services, which is dining, transportation and third-party merchants: the bookstores and things like that; campus safety; technology; athletics; admissions and financial aid. It’s a big portfolio of a lot of different things, and I always joke with people and say that ever since I came to Fieldston there has never been a day that goes by that I’m bored. I’m never flipping through a magazine or scrolling on Instagram or stuff like that because there’s always something to be working on and something to make meaningful and fun progress on.”
Saskia Sommer: “I have sort of an overarching question:- in anticipation of this interview many of my peers wondered what being Fieldston’s CEO entails. I believe many to be very intrigued by the idea and though you have begun to describe this, how might the average ninth-grade student think of your role in the context of their Fieldston experience?”
Kyle Wilkie-Glass “I remember walking around my high school and seeing teachers or administrators that I didn’t necessarily know or interact with and wondering what they do. At the most basic level, a lot of what I do on a daily basis is problem-solving. Even things like budget-building are problem-solving. What I like to do is listen and learn and understand what the landscape is that we’re working on, and think about what solutions we can put in place for whatever the problem is. A lot of the students, faculty and staff that work with me will tell you that something I say a lot is ‘in the spirit of brainstorming…’ because I am a big believer in putting every possible option we think we have on the table when trying to problem-solve. In reality, when you’re surrounded by a team that has strength, you’ll be able to really critically look at all these ideas that people put on the table and take a piece of ‘this’ from ‘this one’ and a piece from ‘this’ of ‘this one’ and build it together. Because you’ll have that multidimensional view of things, you’ll problem-solve in an even more profound way. Again, not that I want every problem at this school all the time ending up on my door-step, but that is what I do a lot of. Problem-solving and trying to understand what some of our options are and how we may need to re-deploy resources or deploy resources to help with different problems that we have.”
Saskia Sommer: “I would love to hear about your priorities for the year. I know that in the past you’ve been in similar roles that require the adaptability you describe like the COVID-19 task force, working with school finances or being the Interim Head of School. From those collective jobs, now putting a little bit of everything into one with this position, how do you intend to use your past experiences both at Fieldston and Sarah Lawrence to guide your current role?”
Kyle Wilkie-Glass “I’ll say this. I wish I had been an ECFS student when I was younger because I think I would have really loved it here. I think a lot of the things that students learn at this school in terms of broader thinking – thinking about systems and policies – are the things that I spend a lot of time thinking about on my own. I really define myself more as a generalist of sorts than a specialist in different ways. What I mean by that is that I like to understand the broader big picture behind everything.
While there are plenty of times I have to dive a little deeper into a tactical level and really understand ‘what are we doing that will support a strategy,’ I rely on a team of really phenomenal people at this school who manage those functions that I mentioned before with ease and with a lot of talent.
Some of the things that I most look forward to in my role are working with students, faculty, staff, parents, guardians and the P+T association. I’ve worked a lot over my time here with the FSG Co-Presidents to understand where each constituency is and also help make great things happen for those constituencies. Over time, it’s always different and that’s just part of the flavor of what comes with dealing with constituencies and leadership of constituencies.
One of the things that I am really passionate about that is part of my role here now is resource allocation: thinking about how we make sure the school’s resources migrate to the buckets they need to migrate to whether it’s financial aid, program expenses, field trips, personnel to support great teaching and things like that.”
Saskia Sommer: “That’s so interesting; thank you so much for sharing. Can you walk me through what that resource allocation looks like as well as the wins for specific constituencies that you discussed and have been involved in?”
Kyle Wilkie-Glass: “Yes. So, we are in the midst, right now, of some of the most consequential processes of the year because every fall, with the Finance Office, I begin to put together a sort of operating budget for the next year. Then, every January, we present a proposed budget to the Board of Trustees that votes and approves the budget, and then we begin our re-enrollment process based on the new tuition level. Then, we very quickly go into the enrollment process and enrollment season to bring new students and new families in. So that process of resource allocation really begins at a constituency level with budget managers. For instance, ‘The Fieldston News’ is part of student activities which is part of the upper school budget. So, Dr. Bobo works with ‘Fieldston News’ advisor Bob Montera who works with the Co-Deans of Student Engagement to understand what the expenses are and how they’ve changed from this year to last year. That translates into Dr. Bobo’s budget which translates into the whole school budget.
So, what we effectively do at the highest level is take a tuition rate, multiply it by a number of students that we anticipate being enrolled, net out financial aid and then we also net in things like annual contributions from our Orange Fund, revenue from our investments, program fees from things like the summer camp and after school activities that we run and any other kind of revenue that we might generate over the course of the year including some smaller state grants that we might get here and there. If you think of that small example of ‘The Fieldston News’ and the printing costs and different costs you have there, you can only kind of imagine how it expands over time. We go into that process very intentionally because we want to pay faculty and staff as competitively as we possibly can. We also try to control the cost of tuition which is one of my bigger concerns about independent schools nationally is the rising cost of tuition and affordability for families.”
Saskia Sommer: “For sure. That makes a lot of sense, and I think it’s intriguing to hear you talk about the intricate systems behind these budgets and allocations because it can seem more direct than the reality. It’s also interesting to hear about factors that seem indirect but actually directly impact the student body. What are some of the ways that being in a role with less student interaction you try to connect with the student body?”
Kyle Wilkie-Glass: “Ms. Solano who is the Upper and Middle School Learning Center Department Chair and I share an advisory. It has been a really fun experience because it has kind of let me on the ground to walk through a student’s day, walk through a student’s month and walk through a student’s year. I can’t believe that in a few weeks [my advisees] are going to be registering for their junior year classes. It shows me, really, how quickly everything moves. One of the things I’ve always enjoyed is having a relationship with the community.
This is a new office for me, I used to be located in the 600s, and one of the things that I actually love is having baskets of snacks because kids are coming up to the 200s for different classes and whatnot and will sometimes pop in and grab something to eat, and it will give me an opportunity to introduce myself and say hello. Even though the upper school, at around 600 kids, can feel like a big community, it’s actually a pretty small community. It’s nice to make meaningful connections with people. It’s nice to know that this one student really loves Taylor Swift or that this one student is having a difficult time because they just lost a pet. It’s also nice for me because I’m able to share moments of myself and my life with members of the community.
One of the things that makes me most proud is that this year I had a seismic change in my life when my daughter, who is in Pre-K, started going to ECFS. So, I get to see things a little differently. Most mornings, we park up near Tate and walk over to Fieldston Lower and I get to see a different side of things. I get emails as a parent. Sometimes, I get an email from myself as a school administrator to me as a parent. For me, what it really underscores is how intentional of a community this is. It has opened up a different door to things because I’m spending more time in closer proximity to other parents and they’re, of course, Pre-K parents and not high school parents and whatnot. It just gives me a much different appreciation for the ECFS community which I loved before, and I love even more now.”
Saskia Sommer: “It’s nice to hear about the many ways your role in the community has adapted and changed not only professionally but through being a parent and having that experience. First of all, congratulations on being Fieldston’s first Chief Executive Officer. Being the first, what is not only the precedent you want to send, but the message you want to communicate being in this role?”
Kyle Wilkie-Glass: “First of all, I think the biggest message I want to send is as CEO, I work very closely in partnership with Mr. Algrant as Head of School. Really what this allows us to do is each have a discrete portfolio of responsibilities to advance the school’s educational mission in different, but meaningful ways. Mr. Algrant’s work on the Academic Program, the DEI Program and Student Support and Wellness is extraordinarily worthy and extraordinarily meaningful, and there’s a lot of strategic energy that’s being invested on that side of the house. In order to allow that to happen, what I’m able to do is kind of take that other portfolio of services and manage that in a parallel way so that we can really start to move the school forward in ways that will have a positive impact on students and families.”
Saskia Sommer: “How do you believe schools might benefit from having the position of Chief Executive Officer, especially one that works in parallel with the Head of School?”
Kyle Wilkie-Glass: “Just like I said before, the upper school can feel like a really big place, but really it’s in fact a small place. It’s the same with the school as a whole. There are a lot of moving parts with any organization. There are even more moving parts with a not-for-profit organization operating in New York City across two campuses which are, in fact, four different divisions or four different schools. There are more than 600 employees, and it really allows the school to allocate the things that any not-for-profit organization, school, college or university would rely on one person to do to really then rely on two. I’m fortunate to have a really strong partnership with Mr. Algrant, and I was Interim Head as he was selected as Head. I really was able to see, understand and meet him and know all the skills and talents he brings. That’s a really fortunate thing for both of us to be in these roles where we can lean on each other but also work independently.”
Saskia Sommer: “That’s also great to know that you have the perspective of not only now being CEO but also being Head of School yourself. I would imagine that’s a very valuable position and experience to draw lessons from. What are some of the lessons you’ve learned in this role, throughout your time at Fieldston or whoever you choose to interpret the question? The lessons are likely ever-evolving as your role continues to evolve with parenthood and whatnot, but what are the things you have learned and the things that motivate you to continue contributing positively to the Fieldston community?”
Kyle Wilkie-Glass: “The first thing, and this has been a throughline of my career for the last three years, is that we have to be constantly innovating. We have to constantly understand that the world is changing, the contemporary student is changing, the contemporary teacher is changing and the contemporary classroom is changing. Look no further than before and after the pandemic for some really kind of stark examples of what worked and what didn’t work and how we met students then and how we meet students now. I always say to people that you can never take a snapshot of success and continue it decade after decade after decade after decade.
One of the most important things in leading a school is driving innovation and helping to elevate some of the phenomenal ideas that we have on the ground here for students, faculty and staff. We have an incredibly devoted, incredibly talented and incredibly creative faculty and student body. Every student and parent that I talk to says that to me. I see that as a parent, too. Just like all of us challenge ourselves creatively, one of my initiatives and goals is taking the ideas of our faculty, staff and students and elevating them and giving creative license to folks so they can see their ideas come to fruition.”
Saskia Sommer: “You mentioned earlier that you’re a creative person; for the more creative student who is also a problem solver, how would you say that creativity factors into certain executive skills?”
Kyle Wilkie-Glass: “I joke with people every once in a while because I say, ‘I hated math in high school. I hated it! A lot of what I do now is addition, subtraction, division, multiplication and percentages in pivotal data here and there. And I do a lot of different things with formulas and whatnot.’ At my heart, I really am much more focused on the arts than the sciences. That’s just kind of where I gravitate to and where I feel most comfortable. The creative thinking element of that really has to do the most with my personality in ways.
I love to organize; I absolutely love to organize. I can’t tell you how many times I’ll put different bins, clips, tags and all these different things in the junk drawer in my kitchen. In a funny way, I think managing and leading a school is similar to that. It’s really thinking about where we put things, how much space they occupy and how much importance are we assigning to those items by them being in the ‘kitchen drawer’ and not in the ‘basement,’ ‘bathroom’ or whatnot. At kind of a thematic level, I do enjoy that. I do enjoy sorting. I enjoy understanding taking things apart and putting them back together. It’s one of those things where I find myself lost in the work the most or in those points of time where I can really just get into it, and feel it and be able to understand it and almost see from the insider’s perspective. Every day your perspective changes on things. …That was probably a lot of gobbly language.”
Saskia Sommer: “No, that makes a lot of sense!”
Kyle Wilkie-Glass: [Laughing] “It does? I’m glad you think so!”
Saskia Sommer: “I love it. I’m very big on the metaphors and the comparisons, so that does make a lot of sense. Thinking about you as a high school student and your recollection of walking past administrators and not quite knowing who everyone was- I think we’re lucky at Fieldston in that many administrators’ roles are transparent and defined- what do you think you as a student would want from you as the Chief Executive Officer? This might be a cliché question, but did you envision yourself taking on this sort of role? What might you say to that high school version of yourself?”
Kyle Wilkie-Glass: “Ooh, that’s a good question. I’m a gay man, and I was not out in high school. High school for me was more of a discovery of myself. It was a discovery of who I wanted to be and where I thought I could go in life. I have to tell you, I’m living a life of happiness that I never thought that I might have when I was in high school. Things were a lot different when I was growing up, and I’m not that old either. To be married, to have our daughter, to have our daughter [at Fieldston], to leave this campus every day and feel fulfilled, to have relationships with people within the community who share that LGBTQIA+ identity, to feel supported and affirmed and to march in the Pride March with the school: all those things really help me feel like this is the right place for so many people, and everybody, for the most part, benefits from finding their people and finding people that aren’t like them either and forging lifelong friendships and relationships. I have one high school friend who is my best friend to this day, and there are many people here who will be in the same boat. I don’t know if that answers your question.”
Saskia Sommer: “Well that’s an amazing answer. Do you think that as Chief Executive Officer you have the capacity to affect change within Fieldston itself in terms of making it a more inclusive space? High school, no matter the place or time and even if you’re attending an incredible school like Fieldston, will have shortcomings, trials and tribulations. This is an inevitability of growing up and the reality of any high school. In spite of this, how do you want to use your platform and your role to continue to make Fieldston more inclusive?”
Kyle Wilkie-Glass: “That is a great question! I work a lot with Keeniun Brumskill, our Executive Director of Community and Social Impact, and I think the thing that we keep returning to so frequently is ‘how do we continue to shape ECFS to be a place where people want to be every day, where they discover joy, where they are able to deal with the challenge of the academic life and where they feel supported socially and emotionally?’ That is going to be a day-to-day challenge, goal and objective of nearly all administrators, faculty and staff here too. I’m a big believer that nothing is set in stone, so we reinvent ourselves every year and have the opportunity to reinvent ourselves every year as an institution. I’m really excited by the way students have led a lot of those efforts, I’m excited by the ways Mr. Brumskill has led a lot of those efforts and gotten other administrators involved in those efforts and I’m always happy and excited to be part of those.
Saskia Sommer: “You mentioned any school is annually presented with the opportunity to reinvent itself, what are the intentions you’ve set for this year and those to follow? What would you like to see or make happen?”
Kyle Wilkie-Glass: “I’ll tell you that in the short term, we have our New York State Association of Independent Schools Decennial Accreditation coming up, and that’s something that I’ve been chairing for the last year and a half. I’ve been working really closely with all of the committee chairs to produce what is our self-study first. Then, in April, we’ll have a visiting committee come in. It’s an important consequential moment for the school because it not only checks the box on the accreditation but what the self-study does is give us an opportunity to look in the mirror and evaluate how we are doing in different areas. It’s also the perfect set-up for our strategic planning processes that will follow. That’s something we’ve been working on for about eighteen months and we’ll be working on for the next few months and then come April, we’ll be able to celebrate because that’ll be complete, and then we’ll start to plan for the 2034 Decennial Accreditation which is a long ways away.
The second piece is that annually, our enrollment season is an important moment for us. The average ECFS student spends about 9.9 years with ECFS. I mention that because 9.9 years in the life of any student is a long time, and I’ve even known parents who have been involved in the school community for around 24 years. When I’m reminded of that, it first puts into perspective that my time with the school, even starting in 2016, is short in comparison.
We also have a long and rich history, and what we have accomplished as an institution over time is nothing short of remarkable. To go back to my earlier point, the enrollment season is really when we’re understanding the students who have expressed interest in Fieldston and applied to come to the school. In many cases, particularly in sixth and ninth grade, we have so few opportunities to bring in new students. It’s extraordinarily competitive, and we make a lot of very difficult decisions throughout the admissions season. Come September, we have a lot of new faces and a lot of new people being introduced to the ECFS community- all of whom have some connection in some different way. They know some current student, or a faculty member that they used to have in another school is here now, or their parents or grandparents went here or some people just stumble across the school and said ‘this is the place that I want to be, and this is the place that I’m in love with.’
I love that period of welcoming immediately following the enrollment season through September because it’s really our opportunity to bring people into the school. There’s something so incredibly special about knowing that we’ve got four-year-olds through nineteen-year-olds and everybody is at a different point in their journey, but everybody is here for the same thing.”
Saskia Sommer: “I’ve had a wonderful time talking to you. To conclude, are there any broad sentiments you want to express or anything you want readers to know about you or your position?”
Kyle Wilkie-Glass: “My door’s always open. I know that sounds so trite, but my door is always open. Feel free to stop by. Grab a snack- I’ve got a bunch of leftover holiday candy! Really, I think during COVID one of the things that was always front of mind for me was that I never wanted anybody to have a question that wasn’t answered. Sometimes I might encourage you to find an answer to a question, but if students have questions about things, you know where to find me, and I want to meet more members of the community. I want them to meet me, and I want to know them. I want to hear about how they’re doing, and I want to hear about their experience at ECFS. This is a place I look forward to coming to every day, and this is a place that is really very special to me.”
Thank you Mr. Wilkie-Glass for your time and thoughtful commentary.
