Dr. Jonathan King joins the podcast to discuss Riverdale Country School's unique approach to technology leadership. He explains the benefits of an engineering-focused mindset, the strategic inclusion of data teams within IT, and a long-term commitment to building talent pipelines that prepare the next generation of technology directors for the community.

1. Riverdale Country School
2. Toddle LMS
3. Flint AI for Schools
4. Veracross
5. Asana Project Management
6. GitHub

Matt, welcome to Talking technology with ATLIS,

the show that plugs you into the important topics and trends for

technology leaders all through a unique Independent School lens.

We'll hear stories from technology directors and other

special guests from the Independent School community,

and provide you with focused learning and deep dive topics.

And now please welcome your host, Christina Lewellen,

Hello everyone, and welcome back to

talking technology with ATLIS. I'm Christina Lewellen, the

President and CEO of the Association of technology

leaders in independent schools.

And I'm Bill Stites, the Director of

Technology at Montclair Kimberly Academy in Montclair, New

Jersey, and

I'm Hiram Cuevas, the Director of Information

Systems and Academic Technology at St Christopher school in

Richmond, Virginia.

Hello, gentlemen. How are you this

morning? Doing well, got a little bit of spring in the air

here, yes, and the spring travel schedule in the Independent

School Association community is in full force. Indeed, Hiram, I

don't know if you heard about this, but last week, I was in

New Jersey at the NJ AIS advancement Summit, and I got

picked up and taken for drinks by none other than Mr. And Mrs.

Stites.

Nice. He got to meet Brooke. Yeah, I actually

think I've met

Brooke when we were in New Jersey doing the

item writing for the exam. So I hadn't met Brooke before. I did

know she existed. I've hugged her before, but I got to hug her

again. It was great to hang out with her, and it was so

adorable, because she apparently has quite a reputation for

falling asleep at public events, and that poor woman, Bill and I

are having adult beverages at this pub, and she's like, I'll

have a hot tea. It was the cutest.

It was quite the evening. I will tell you, I'll

set it up, though, because we were on an ATLIS call Christina

comes on the thing. And I'm like, wait a minute. I recognize

that that background. And then I see one of my colleagues walking

by, and then I see her name tag, and I'm like, why didn't you let

me know you were here? I'm like, you were right down the block.

I'm like, we could make this work, and then we made it all

work, and it all came together. Came together beautifully. But I

will share something with you, and Christina doesn't know this.

Oh, the next day, Brooke and I were talking, and I was like,

said, You have a good time last night. And she's like, Oh my

god, yeah, it was so much fun. She seems like somebody who gets

stuff done. Oh, there you go. Because Brooke now has like,

this laundry list of things that she's now, like, checking off

her list that she now needs to do based on one conversation

with Miss Lewellen here. So just know that she inspires people to

get stuff

done, women, helping women. That's all I have

for a while, Bill, believe it or not, Bill was just sitting there

observing this whole conversation go down, because I

was like, sir, you just hush a minute. My friend Brooke and I

have something to talk about, indeed, but we missed you,

Hiram. We thought about you. And really, I mean, I'm so close to

you, I really need to just come down to Richmond, and I have

great friends in Richmond. So here we go. I'm going to go on

public record before I leave ATLIS, I am driving down to

Richmond to hang out with Hiram. It'd be great if all of us could

get together in person, which doesn't happen very often. But

in the meantime, I'll take you each separately. Maybe that's a

better approach.

Anyhow. Usually is, trust me, I think it is.

Well today, you guys, we have another

wonderful guest. I'm super excited about this one, and I

know that you guys are just drooling to get these questions

answered, because today we are talking to Dr Jonathan king, and

he serves as the Chief Information and Technology

Officer at Riverdale Country School, which is a large pre K

through 12 Independent School in the Bronx. Dr King, hello

friend. How are you today? And welcome to the podcast. Hi,

thank you for having me. I'm doing great, good Jonathan. I am

from New York, but I'm not from the cool part of New York where

you are. I am from the snowy part of New York where we're

crazy about a certain football team. Oh, you're from the North.

Yeah, I'm from Buffalo,

Rochester area. I'm actually originally from

Boston, so we were crazy about a certain football team, also as a

child. I also used to live in Seattle, so the Super Bowl is a

little tricky for me this year.

Oh, interesting. So did you have a

favorite? Or were you going to be happy no matter what?

I like to make nachos, let's be honest, that

was my focus. We made a lot of good food, and then sometimes we

watch TV.

You are already my friend, okay, so let

me give you a second, Jonathan, to introduce yourself. You come

from a large school, but we would love to learn a little bit

about you and about the school you serve. So let us turn the

mic over to you for a minute.

I have been at Riverdale for 22 years and never

expected to be here more than a handful. And I'm here because I

love this place. We are very fortunate to be this Leafy,

grassy oasis in New York City. I remember the first day I walked

on this campus. I was like, Wait a minute. You. I don't

understand where I've gone. Like, I took the subway, I went

all this way north. I thought I was going to be like, in a

concrete jungle, and we're on 20 something acres of green grass

and beauty, and we have great faculty and great students, and

we're trying to do good in the world. That's not a very

exciting answer, but that is why I'm here.

So did you start 22 years ago in tech, or

were you a teacher, I have a weird history. We kind of all do

in this space, to be honest, so we're open to that.

I actually started working in schools as a

kid, and absolutely loved working with kids. I have a

family of educators, and I tried really hard to not be an

educator, and I knew that that was going to be my future as

like my destiny, was working in a school, but I tried not to for

a while. So I was a technology consultant, independent. I

worked in a lot of different places. I worked in Italy, I

worked in Seattle, I worked in New York, and then kind of

randomly decided that it was time to settle down, quote,

unquote, settle down back when I was around 30 years old, and I

was like, you know, I want to work in a school. I took eight

years to not do it. I have a PhD in fuzzy logic, which most

people say, What the heck is that? And I realized I didn't

want to do that thing for the rest of my life. It's a lot of

math and computer science, which I like but didn't want to do, is

like my future. And ended up in New York on a job, and while I

was here living in my brother's apartment, I was like, I kind of

like it here. Maybe I'll see what happens if I stick around.

I actually tried to get a job as a public school math teacher,

and I have a PhD in math, and the public schools rejected me

and said I did not have the appropriate credentials to

become a teacher in the public school system. And I was like,

Well, I guess if I can't do that, I will look at something

else. My family has been private school teachers and

administrators and heads of school for a long time. I was a

public school kid, and I was like, I don't know if I really

want to do this. This is a big change. I looked at a few

schools. I got a job offer very quickly from Riverdale, and as I

said, before I walked on campus, was like, why would I not come

here? This is incredible. Figured I'd be there for a few

years. I was a computer science teacher and network and systems

administrator when I first started, and have stuck around

for a very long time.

So for people who are not familiar with

Riverdale, can you help us understand the size and scope of

the school and what kind of families tend to be attracted to

put their kids there?

We are a two campus School in the Bronx.

We're in Riverdale. I have three children who all go to

Riverdale, and one of them is like, we're not in the Bronx.

We're in Riverdale. I was like, well, Riverdale is actually in

the Bronx, but it feels very different. So if you have

preconceptions about what the Bronx is, I think, come have a

look. The Bronx is more interesting than maybe people

realize. Anyway, we have two campuses. The Lower School is a

about a mile away from the middle of our school. We call

them the river and the hill based on being near the river

and on top of a hill kind of makes sense. And it's hard to

say who we attract exactly my sense, and I'll just say, in

full disclosure, my wife also works here. She is the Associate

Head of School for admission and enrollment, so she actually is

the one who is responsible for helping families choose to come

to Riverdale. And so I talk about this a lot. We have a

really clear mission. We want to change the world for good. We

want to do good in the world. We want to turn out kids who

understand how to interact with society and the world and leave

it better than they found it. We're not a school where you're

going to come and just do Math and Math and Math and Math.

We're not just going to drill and kill. We're here to, like,

expand your mind, expand your soul, and help you be a better

person and contribute to the world. And that's actually what

attracted me in the very first place. Like I walked on campus

and thought it was physically beautiful, and then I talked to

the people I was going to work with, and I learned about the

mission that we have, and I was pretty sold,

Jonathan, I actually grew up in the Bronx.

Oh, nice. It was actually born in Hell's Kitchen in Manhattan.

Yeah, shout out to Daredevil. You know, grew up near Fordham

Road, and then we actually lived in Co Op City until I was 12. My

father was in New York City, Fireman on story Avenue, so I

chuckled when you said between the river and the hill, because

not many people know that you are really a stone's throw from

Van Cortlandt Park. That's right, which is the cross

country MKA. I think of the United States as a former runner

spent a lot of time at Van Cortlandt Park. It's a beautiful

part of the Bronx.

Dub Bronx, my wife, Jenna king, was a very

accomplished runner, and she ran event Cortland park all the

time. We eventually actually moved on to campus. There are a

handful of houses here, and so we live on campus. And so I go

to Van Cortland park all the time. I walk the dog in Van

Cortlandt Park. It's beautiful. We feel incredibly fortunate. We

have this massive Park, and I think people don't realize that

it even exists. You kind of think of the Bronx as Arthur

Avenue and some other things that might feel dangerous. And

it is a really varied kind of beautiful borough.

And I love the fact that there's a hill there

called Cemetery Hill. That's right.

Can you give us a little bit more detail in terms

of the size of it? How many students, how many faculty?

Faculty, staff, and then the size of your staff, because,

again, given the size of the school, the size of the people

serving the school, and the roles that they hold and what

they do, is always of interest.

So we have about 1300 students, as most schools,

do we add students at sixth grade and ninth grade, so the

class sizes get larger as you go throughout the school, it's hard

to say the number of staff, because there's the FTE versus

the actual individual human beings, but they're around 350

FTE, I think, in total. But that includes coaches who are part

time. It includes a lot of other positions. I think we have

around 250 teachers. One of the things that I think is really

special about Riverdale is that the majority of our

administrators also teach. I don't, which makes me very sad.

About 10 years ago, I stopped teaching because I felt like I

was not doing a very good job at it, frankly, and that I would be

better for the students if I wasn't their teacher, which was

a really awful thing to go through, and I still miss it

feel like I'm gonna get teary. So when it comes to the staff of

my department. We are very large. We have 16 people in the

technology department. But the technology department is not a

traditional one. So as you all know, some schools have a tech

department, which is basically operations only. Some have

academics rolled into it. We have operations, we have

academic technology. We also have data so our data team is

three people strong. We have an associate director of

administrative systems, Jennifer Davenport, who some of you know,

and she's great as Bill just gave the thumbs up, and she runs

a team that has the registrar. Actually, there are four people

on her team. So there's a registrar. We have a data person

who handles medical data, and we have our person in charge of

student and adult attendance, that's a team of four people,

and that would not normally be in a tech department, and it

took us a pretty long time to come up with that configuration.

There aren't a lot of structures at Riverdale that cross both

campuses. And so you know, when you're a multi campus school,

you have slightly different set of conditions, like our Lower

School is on its own campus, but the middle upper school is on a

separate campus, and as a result, we have slightly

different structures at each of those places. My operations team

has people at both campuses. My academic team has people at both

campuses. But the reporting structures can be a little bit

weird looking based on local conditions, but we have a very

big team, and everyone is busy, there are times I think to

myself, like, Are we too large? And I'm actually right now in a

moment where I actually want to expand. I'm considering what it

looks like to hire a full time programmer right now. My

background is computer science. I am a programmer. I write lots

of software for the school, but I'm also running a team of 16

people, and it is not always easy to be the person on call to

fix a software error or a problem when you're also

managing such a large group of people. So you know, we actually

might get larger in ways that make a lot of sense to me. So

I'm

curious about that potential expansion. What are

the areas that you're seeing would necessitate someone in

your role to absorb into your department.

There are two places we might be expanding.

One is, as I mentioned you guys before we started, we have a

byud program at the upper school, and we're considering

what it looks like to move that to a one to one program that

includes support, right? If we no longer own the machines, if

we no longer service the machines, or if we now have to

service the machines, we need to have personnel to do it, and we

might be okay with the people we have now. We have two level one

support folks at the Hill campus, but we're not certain.

So we're trying to, like, run some numbers, figure out what

breakage rates look like, what does return rates look like, and

all of that. So we're trying to figure out what that might look

like. Also, there's, you know, financial component to do, we

start buying all these machines that we give to the kids, so

we're trying to work through all of that, and then part of it

becomes staffing. The other piece is what I mentioned

before, which is programming. And I'm sure we'll talk about AI

in depth at some point, but I'll just say AI is incredible at

creating programs, but you still need a human being who

understands what's going on. And right now, I'm that person. I

have a few people on my staff who are actually pretty good at

this, but it's not their focus, like they have other

responsibilities. I can't have them writing software. And for a

long time, the thing that I prided myself on was creating

the glue that brought all of our systems together, that moved

data from place A to place B. Many of you are school Cal

customers that lets you bring your Veracross calendar into

Google. And I think now Microsoft and I actually built a

version of that and worked with Aaron and gave him all of my

code and said, Please make this product so I can buy it from

you, because I can't be the one who does this anymore for the

school. It just takes up too much time. And so I'm pretty

good at these things, but can't do them all myself. And so I see

a long list of places that AI can actually help a person on

staff make really useful tools. One of my people, I met with him

this morning. We're moving from one LMS to another. I don't

think I want to name it right now in this way, but part of

that is we want to give people a way to view their data. From the

current LMS. And he this is kind of an incredible story, I think,

on a plane last weekend, on only his phone, he built, using AI

and GitHub, a program, a web service that will allow you to

upload a common cartridge format from your LMS, and you have a

full viewer that shows you all of your content from your class

that would allow you to copy and paste it into another system to

aid in migration. You know, five years ago, that just wouldn't

have happened, right? And if I needed that thing, I would have

been like, sorry, guys, we're just not going to do that. Or I

would have put an incredible amount of my own time into

building it. He did it on like, a three hour plane ride. It's

pretty incredible. Yeah, I was kind of blown away. And he's

also a programmer in his background, he's one of our

Academic Technology Specialist technology specialists, and he's

amazing, and if he spent all this time making tools, he

wouldn't do the rest of his job, because there are a million

tools we all needed exactly.

I do want to come back to the AI topic, but I

am interested, given the size of your team and especially your

background, how do you find these people, and do you look

for kind of the best in class, technology people, or is it just

depends on the role? Like, how do you think about hiring?

Hiring is the most important thing we do as a

school. There are two things. My wife would probably say,

bringing the students in admissions might be the most

important thing. I think that both of those have equal

importance. The thing to me is that if you don't hire good

people, then you're stuck with mediocre people. And that can be

fine, and you can be stuck trying to hire, and you can get

someone who feels mediocre in some way, who turns out to be

spectacular, or who grows into a role that is, like, really

impressive. I try really hard to hire great from the very

beginning, and it's the hardest thing that I do. And every year

I don't have to hire, I breathe a sigh of relief. Finding good

candidates can be really challenging. Working the various

networks that we all have sometimes bears amazing fruit,

sometimes not. And I'll tell you that my position on this is that

I won't hire if I'm not comfortable hiring. And so we

have run sometimes a whole year without filling a position

because I want to hire the right person. I have a very high

personal capacity, so when we can't hire someone, I do their

job and I do their job until we hire someone. That's great, the

academic technology person I mentioned who made this program

on an airplane. I hired him in like, November, because I

couldn't get the person I wanted. I couldn't get the

alternate person I wanted. And then I was like, I'm just going

to wait. And our team understands that waiting for the

right person is better than hiring the wrong person, and so

no one is, at least to me in my face, begrudging the fact that

sometimes we go a long while between hires. Another example

of that, I think I waited almost an entire year to hire our

database administrator, and that was because I never found

someone I thought could really come in and understand the

complexity of what we are and what we do, and do it really

well. I waited and waited and waited and waited and waited,

and then the person said, You know what? Okay, I'm ready to

come work at Riverdale. And then we made a deal, and I'm

incredibly thrilled that she's here, because she's doing all

the things that I wanted her to do that I was doing myself for

years, it freed me up. So hiring couldn't be more important, is

the way I view it.

I think it speaks a lot to the school to be able to

hold on to a position without having it filled and knowing

that this is something that we need. Because I think a lot of

times when schools see somebody else stepping in being able to

do that job, they're like, All right, well, then maybe we don't

need to hire this person. You know? Maybe we can handle this

with what we have. And often that's not the case. They don't

see what goes into it. They don't necessarily see what's

missing. So I think that speaks very highly of what Riverdale

values, not only what you value, but the school values, in terms

of bringing that right person on I do want to ask a question

about the programmer that you mentioned hiring one of the

things that we continue to spend a lot of time on, I know I've

talked to Jen about this, is around data and moving data. You

talked about it and mentioned it earlier, is what you see that

position being one that is kind of extending that ability to

connect systems and their data. Or are you looking for somebody

to actually build an application you use the school Cal example,

and thank you very much, proud school Cal user here in terms of

what we do. But are you looking to start developing at that

level, or is it more programming to let your systems play in the

sandbox more nicely than they might do at this point. And is

that what you're looking for?

I want to do both. So a good example is that

I recently made the very terrible decision to produce a

system within App sheet, Google's appsheet, which turns

out, is not available to students under 18. But I did not

know that until I found the very, very buried tech note in

their help documentation. So I built a thing that took a ton of

data out of Veracross. It took a mapping of all of our courses,

which me and a. Registrar built that shows how every course

relates to every other course at the school, and built a tool

that allows advisors and students to go through and

understand all the classes they've taken at Riverdale. They

can see all the possible classes for next year based on classes

they've taken this year, and make a request system. They can

order them. They can say which their priorities. They can group

them together, and it's kind of awesome, and yet kids can't use

it. And the whole point was for kids to be able to use it. And

the only reason I did that is because I didn't have the

capacity, personally or in my staff, to produce that in house

experience in our own ecosystem. So I picked appsheet as the

thing that I use as the platform. And what I want is

someone who can come in and actually say, All right, here is

your massive AI prompt. What you want this whole program to do?

They understand enough that programming to then create it,

to host it, to run it, to give it the care and feeding that it

needs to serve the school, we have a ton of student projects

that are good, but not maintained. And I'm sure some of

you have seen this as well, where your students do something

that's actually really useful to school, like we have a very

thoughtful computer science department. Their capstone

project in their senior year is one where the kids go try to

find a real world problem and solve it. Often, that real world

problem is a river del problem. They solve it, then they

graduate, and then you're like, now what I want to have some

capacity at the school to actually have the answer to now

what be like? We're going to incorporate this now into our

standard practice, and we're going to maintain it. And right

now, you know, we have kids who graduated, who have been gone

for years, who are like, do you want me to make some changes to

the code? I was like, That's very nice of you, but you have

moved on in your life, and we don't want to put an anchor on

you to be back here. So like, that's one thing, and then Bill

the other part is the glue is incredibly important. All of us

know that we have all these different systems, and they

don't all talk to each other. And as much as vendors have come

together to make some common formats, other ones just don't

exist. There is no common format for a schedule that everyone

understands that says when a class actually meets. And so

that's a real problem. One of my real world problems I want to

solve right now is how to get revna, which we were customer

number two for, to actually know our schedules so they can tell

us. These are the kids who should be in front of you right

now. And so these are things that I, as a programmer from my

background, want to solve like you wouldn't believe, like, I

want to dig my teeth into all these things, but that's not my

job anymore. So we need that capacity to be here. Somehow, I

got asked last week, like, Well, why don't you just hire a

consultant or a part time programmer or, like, fill in the

blank for some non full time person. I was like, there is an

incredible benefit that we all see from someone who understands

the culture that we operate in and hiring someone who might be

low cost, who might be overseas, who might be, you know, fill in

the blank, someone who's just not of your school, I think,

introduces a whole set of challenges that makes that

harder to do. And I like the notion I'm an in house kind of

guy. I have only recently out housed things. That's a terrible

term, but I've only recently moved some things out of the

house because of staffing issues. If anyone out there is

an incredible network engineer, call me the money that we offer

for positions that we have can be not as good as industry, and

it becomes harder and harder to fill seats with really good

people who are willing to work here. Like I wanted to be in

education. I wanted to work in a school, and I knew that from

when I was a kid, my family knew that from when I was from when I

was a kid, and so I was willing to come to Riverdale and make

less money that I would have made anywhere else, because I

felt the call. That's hard to instill in people. I want to

find a programmer who wants to be here, and that's a real

challenge. And I also need to get my leadership to agree to

let me hire a programmer. So if they listen to this, let me

through your programmer,

there you go. You've laid out your case.

Well, I think that it lends itself, Jonathan, to a question

that I had, and you're already sort of touching on it. So I

want to just call it out. Is that you have a very extensive

educational and experience background in tech specific

endeavors computer science, so naturally, that is going to

impact your approach to serving a school, and you've been

talking a little bit about that, in that you just want to program

some solutions. I would imagine that you're probably a dream

customer for a lot of your platforms, because you're giving

legitimate solutions to problems that you run up against with

those platforms. But you know, coming into the education space,

especially a K 12, I guess I'm curious, is this something that

you're actively thinking about is how to take solutions that

would probably make more sense in a corporate setting and

actually say, no, no, just because we're a K 12 doesn't

mean that we shouldn't have those same programmed solutions,

you bring an engineer's brain to the work that you do, which I

think is sort of rare, so it's less of a question and more of a

calling out, but I wonder if you think like that, if that

resonates with you.

Very much. So I am an engineer like my actual

undergraduate degree was Electrical and Computer

Engineering. My PhD is in math and science, or math. In

computer science, and my career is based on providing solutions

to people with problems, and so I view that as my whole reason

to be at Riverdale. I view myself as the efficiency expert,

a process person like I want to see problems actually, I can't

help but to see problems and then try to think of ways to

make them go away. I hate to see someone bashing their head

against the wall doing something that could be done in less time

with more training. And so I go around here trying to find, I

guess, not trying to find it, because it's easy to find things

that could be improved everywhere, including within my

own team. It's not like we're perfect. That engineer brain

almost never turns off, which is sometimes a problem, I'll be

honest. Like, sometimes people don't want you to come and solve

the problem. They want you to listen to the problem, and they

solve it themselves. And so, you know, learning how to coach in

that way has been, I think, really important for me, but I

can't help myself. I want to fix everything, and I want to glue

everything together, and I want to make things more efficient.

And I might be a dream customer to some people, but I also know

that to others, I'm like, I'm a very vocal critiquer of systems.

I'm very happy to give incredibly clear feedback on

demo calls. I don't hold back. I try to give all my feedback

kindly. I'm not doing it in a mean way. I'm just saying these

are things that I see, that I think are important, and if you

want to sell that product to me, this is what I need you to do in

order for that to happen. And most of the people I work with,

I think appreciate that. I'm sure I've rubbed people the

wrong way here and there over the years, because being direct

is not always kind, despite what the pithy saying is.

I think it's funny, because you and I have known one

another just given proximity and the common people that we know

for a while, but it's funny your name comes up very often when

we're talking to the same vendors, oh, you know, you

should talk to Jonathan over at Roberto, you know, he's dealing

with the same thing, he'll be a great person. You know, Roven

was a great example of that school. Cal was another in terms

of where those things come up. So I value the fact that you

take that to them in that way, because, again, it's how we get

at and solve the problems that we're talking about. But one of

the problems that I want to ask you a little bit more about,

because the idea of just how you built your team and the work

that goes on there, you know, we've talked on the podcast

about who the next generation of leaders are in developing a

pipeline for those people, and you touched on something that

I've been thinking about here at MKA, and how we might leverage

it a little bit more. But how do you think about, or do you think

about, and do you have any success with exposing people?

You know, I came from a family of educators, you said the same

thing. How do you think about exposing people that you want to

bring into a school that are going to solve your problems, to

the values and the benefits of working in a school that might

otherwise be thinking about that corporate environment, to really

sell them on that? What have you done to help that process along?

Because I think that's something that we all struggle with. I

think there are great people out there. I think there are people

that if they saw what life is like working in a school, would

look at that difference between the corporate and the school

life and say, Actually, this is more how I want to live my life,

doing the things that I love. How have you worked through

that?

I could talk about this forever, but I won't.

I'll tell you that at my core, I believe that working education

is doing good in the world. And every interview that's a part of

that conversation, every conversation I have with people,

that's a piece that comes up. We aren't here just to take parents

money and then have a kid graduate and go to a school with

a good name like that. Isn't why we're here. If you want that,

there are other schools people could go to. We want to actually

help people be better people, and that works for our staff

also. So part of my like spiel, I guess you could say, when I'm

doing my hiring, is, obviously I talk about the fact that schools

have more vacation time. But it's not just about vacation

time, it's about quality of lifetime. I actually have 13

year old twins, and one of them was asking me yesterday about

jobs, and I just mentioned to him, somewhat casually, you

might only get two weeks of vacation a year with your first

job. And he just looked at me like, are you crazy? How Does

anyone live like that? I'm like, honestly, I feel sorry that

people do have to live like that, I recognize economics and

the reality, and feel incredibly fortunate that I've landed in a

place that values me as a human being and understands it for me

to be a high functioning, useful human being in our environment.

I need downtime, and so, you know, we have five weeks of

downtime in the summer. Officially, unofficially, we

actually spread that around the school year because we don't

want everyone out at the same time in the summer. Time in the

summer bill, it's hard. I feel like people who get it get it,

and people who don't don't, and you're asking, like, how do you

bridge that gap? And I have failed many times to bridge that

gap. People are like, Oh, you just don't offer as much money.

And I was like, okay, but we offer a lot more. Sure, and if

you're willing to kind of sit with it, maybe those things we

offer will sing to you in some way. We offer professional

development, a lot of it. I have a very generous PD budget. I

don't actually get to spend it all every year. I've argued

every year for more and don't manage to spend it all, which

makes me a little bit sad. I usually spend it on other

people. This was, like, the first year where I'm like, You

know what? I think I need to get out there a little bit more.

It's part of the reason bit more. It's part of the reason I

joined ATLIS. Is part of the reason that I'm on this podcast.

I'm like, you know, I think I'm relatively well known and seen

here in New York, but I can learn a lot more from more

people around the globe and around America. And I was like,

I want to have more contact outside of my local sphere. And

PD, is, I think, really important a lot of companies

don't invest in their people. Riverdale really is willing to

invest in their people and help you grow. And one of the most

important things to me, and one of the metrics by which I judge

of my own success, is this is my little quote, how many directors

of Technology have I produced? If I haven't produced any

directors of technology, I kind of feel like I've failed. People

should view Riverdale as a pipeline. And I tell every

person in every interview, I ask them the question, what do you

want to do next? And what can I do to help you get to that

thing, whether that's internal or external, whatever that is,

if you think in 10 years you'll meet Director technology, let's

have that conversation now. Don't hide it. I'm not

threatened by it like I love my job. I'm doing great at my job.

No one's kicking me out of my job, but if they do, are you

going to be in the right position to take that job? Let's

make sure you have the skill set to it if you want to be a D O T

let's have you leave, grow the wings and fly. And I've had a

few people who have left income do T's. I've had a few people

who are d o t s, who came back and took shelter at Riverdale,

as I kind of like, are working out what's next for themselves.

And I'm proud of all of those people. We are a pipeline, and

that's what you said earlier. Like we really need to make sure

that this is not a job for life. This is a step on everyone's

individual journey, and I want to make sure that that step is

really positive. As much as I said that a year without hiring

is a great year. A year hiring because someone left to

something better is the best year, right? It means a friend

of mine, a person I care about, a person that I tried to help

grow

grew That's really incredible. I respect

that, because I feel like after I got my MBA, it changed me as a

leader, and especially from my lens as a female leader, a woman

operating in some predominantly male environments, it changed me

in such a way, Jonathan that I became an advocate, if not an

outright proselytizer, around the value of getting that type

of professional development for women who had similar career

goals. So I have to tell you that, like when you just said,

how many technology directors have I produced? My little heart

went a flutter, and I could see the guys reaching for the pen

too. What a lovely fingerprint to leave in our community. The

reason I brought up the NBA thing is because I believe that

I might be on either the fifth or sixth woman that I have

mentored in my career, who is currently pursuing her MBA,

because she knows me, and that literally fills my soul. So to

hear you say, how many tech directors have I produced? What

a delightful sentiment. Thank you for that. That's incredible.

Thank you also, because you just mentioned women

in leadership, I would also be remiss to not state that we have

six of our people on our team are women, which is, I think,

smaller than it should be, but I think much higher than the norm.

So Jonathan, your ethos is very powerful. I'm

wondering, is that part of the secret sauce that Riverdale has

across its entire constituency, or is this specific to you? And

the reason I asked that question is, I'm curious, where are you

on the pipeline?

That's a loaded question. I'll start with the

first part. So I do think this is a school wide opinion. I

think that I feel it more keenly than most. We are a dean based

school at the middle upper school, so we have a dean per

grade. So you know, grade six, seven and eight are static. They

stay with their grades, and grades nine through 12 travel,

and that is an incredible pipeline for a school. So if you

have a dean who travels nine through 12 and then finishes

that deanship, they often, in the olden days, they would

repeat. Nowadays they're often finishing and then moving up in

the administration, either within the school or elsewhere,

and it gives a real opportunity for internal people to grow.

Dean's an amazing position. You still get to teach. You get to

work with students in a much more focused way. You're working

with parents in another way. It's a really good pipeline to

become a dean of students or a division head, or, you know, a

lot of different things. That's, I think, our main internal

pipeline. And I think we all believe very strongly that we

want people internally to enter it. And every once in a while,

we hire externally. It's not like this is a closed system on

a personal level. I don't know what's next for me. I have three

children who are at Riverdale. I have twin boys who are in eighth

grade. My daughter is in 10th grade, so she's. Seeing the end,

which is incredibly terrifying for me as a parent, and exciting

all at the same time. And you know, my family talks a lot

about like, when the kids graduate, what happens next? I

mentioned to you all that I live on campus. I've been here for 22

years. My wife and I met, actually the first day of

orientation for new faculty in 2004 she was dating someone at

the time, so I had to wait a little while for we worked it

out. But, you know, we did, and here we are, three kids later,

and jobs that we both love, that feel rewarding and great, but at

some point my kids are going to graduate, and I tell you, no

one's going to bury me in the backyard at reveal country

school. So clearly, something is going to come next, and we're in

like, hot debate about what that might be. And to go a little

more like in the detail, like, there isn't a good pipeline at

the top levels of schools. There are better pipelines lower down.

And so once you hit a certain level, it's hard for tech

directors, which I'm not officially, I'm a Chief

Information Technology Officer, but colloquially, I'm a tech

director. It's hard for us to move to other positions. Like, I

know some folks who become division heads and heads of

school, there's a real pipeline for that, but it's small. It's a

rare jump. I think that happens. Operations is a more likely

place for people to go. In tech, it's a place that I would be

pretty comfortable, but you have to go in a way that makes sense.

You have to be in a school that supports that type of structure.

So, you know, our high leadership is pretty stocked

right now, so I don't think there is anywhere for me to

literally move at Riverdale, but I'm also not trying to leave

Riverdale, so like, I'm fine where I am, but in five years,

if we have this conversation again, I will have a very

different answer for you as my

guest, I have one more pipeline question for you,

and I know we're eager to talk about the ever present topic of

AI, but with regard to the pipeline, I came To MKA as a

student teacher. I wouldn't have known what independent schools

were really about when I grew up, independent schools were

just the Catholic schools you know, that I grew up with. And I

will say that I took inspiration from actually Hiram school for

this question, because it's one that I'm pursuing here at MKA is

right up the road for me is Montclair State University,

which is where I went, which is why I ended up in MKA. But I'm

interested in going in and talking to their comp sci

departments. They have, you know, a mass people that are

working on their cyber security degrees to see if they are

interested in doing, like, short term internships at the school.

Because when you think about that pipeline, like people

coming out of college might not even know that schools, let

alone independent schools, are an option. Have you seen anyone?

Have you considered going down that road for that pipeline?

Because to what you described earlier, you've got to get

somebody to apply to sell them on that That's right. I'm trying

to think of like, how do we develop this? Like you developed

your student teachers back in the day where you might have a

placement in a school that was like, Oh, I didn't realize this

was here. How do we do that with people that we need to bring in

in our fields?

So you're talking about outreach, and I think

outreach is incredibly important, but also hard to put

time into. So the first thing that happens every time we have

a position to fill is we're like, where are we going to post

this? Like, how are we going to get the word out? How are we

going to get the right eyeballs on these postings? In a world

where you could get 500 applicants to a position, or

where every applicant is just firing off hundreds of

applications. It's really hard in this attention economy to get

the attention. And I like what you're describing, like, you're

basically going to the source, like, get to folks before they

get kind of stuck in the mill and don't know what to do

anymore. I've thought about doing what you just described.

I've just never had time to really do it. I used to have

some relationships to the local colleges. They've largely

frittered away because people leave, I would go to their job

sites to post our positions. But even interns can be a challenge

in terms of just having time good time, like you want the

intern to actually have a good experience. You don't want to

hire someone and give them a promise of learning and

mentorship and then kind of leave them high and dry with

like, some mundane tasks going back to my own, like, pre

history, one of my very first jobs, I was hired in the summer

to work at bolt Brad can Newman, not the school, but a company in

Boston, the company that invented hard drives, funnily

enough, and I worked for their facilities department,

maintaining their computers. And I was essentially an intern. And

I learned something then that has stuck with me forever, which

is that I just want experience, so I'll happily take an unpaid

internship. That's all I wanted. I just wanted experience

somewhere in the world. So I understood what it like to have

a job and go to an office every day and all these things. And

the company was like, so we actually can't hire an unpaid

intern. We have to pay you. And I was like, wait, what? Yeah,

that's a new thing. Well, this was a 35 year old thing. Maybe

they were like, on the cuff, who knows? And I was like, in

hindsight, I was like, That makes so much sense, like, I'm

doing real work for you, and I'm expecting something from it, and

they're going to pay me, and they're going to mentor me. And

I had a great mentor. His name was Frank, and I love that guy.

And he. Taught me a lot of things about what it was to

work, and what I feel is that I don't know that I could pull

that off for an intern. Now, what we would often do somewhat

similar what you described, but like, we would hire a student

who is graduating to work in the summer, and that can be loaded,

because there are equity issues, and we have a lot of FA

students, and we have financial aid, and you don't want your

summer pool of workers to look like the kids who have FA

because there's something wrong with that, in some ways, to me,

and also wonderful that you're giving someone an opportunity to

get a job and make some money. And so over time, we've kind of

up staffed and then stopped hiring students, which makes me

sad. And so I look for opportunities where we can bring

in people, but it's a challenge, and I wish that I did this

better. I'll say it like that, you're saying things bill that

really resonate with me and that I feel like I have not done as

well as I could have. And we should have pipelines in this

world. We should have people excited to go into education.

And there are a lot of reasons why that isn't happening right

now, but I'll tell you, when I was a kid, being a teacher was

something to be proud of. It was something to aspire to, and I

feel like that is less true now than it was then, and I still

aspire, in some ways, I still aspire to be a teacher. I

haven't quite gotten back to it. Maybe that's my next chapter.

Hiram, go back to be a computer science teacher. That would be

pretty awesome.

So let's move into AI, as we've alluded

to. We want to talk to you a little bit about that, because I

think that it sounds as if you've leveraged AI a bit on the

operation side in terms of just running a more efficient

department, running a more efficient school, my guess is

what you've been talking about in terms of how you let your

students get involved, that they also are probably using AI. So

let me just lob that one over to you, and have you talk to us a

little bit about how the school is thinking about AI and some of

the use cases that you've been deploying to date,

I think the most important use case is students.

How are students interacting with AI? Our philosophy started

when chat GPT hit the scene in a very public way. Everyone

started to freak out about it. We had known for years that this

was coming. We'd been thinking about it for years. It for

years. It wasn't a huge surprise to us, but yet it was still like

a really big tipping point, and we determined early on that AI

wasn't something we were going to block, it wasn't something we

were going to stop, it was a thing that we were going to

embrace. We want to be perceived and to actually be a leader in

how AI can actually enhance someone's education. We don't

want to take humans out of this process. We don't think that AI

is going to become the teacher, but an AI agent can really help.

So we eventually purchased Flint, which I think many

schools have done. We have Toddle at our Lower School,

which has AI components, which are actually very impressive. We

have turned On Gemini for all of our students. They're allowed to

use it. We have explained, ad nauseam, frankly, our AI policy

with everyone. So every student should know that the teacher

gets to set the level. It's level zero through four, zero

being nothing, one being essentially, it can act like a

tutor. And then two, three and four being it can generate

content of various complexity. We very much felt like aI should

be viewed as a tutor in a lot of ways, and so we aligned our AI

policy to our tutoring policy. I assume many schools have a

tutoring policy because we don't want tutors doing students work.

So we set guidelines about what looks like to get external help

on your work. And a tutor doesn't mean a paid person. It

could be me as a parent, it could be anyone. Could be a

friend. A friend could tutor you. So we have a tutoring

policy, and the AI policy goes pretty much in line with it. The

end result is that we want to develop kids minds. That's what

we're here for. We're not here to develop kids who can't

reason, who can't think, who can't solve problems, but AI can

be an incredible tool to help you do all of those things. So

our teachers are empowered to thoughtfully use AI in ways that

help to enhance and to further the mission that we have at the

school. Some teachers are all in. It's like really impressive

to see, and not all in, in a way of saying we're using AI for

everything. They're all in around AI is a tool. It's yet

another tool in my very huge toolbox, and I'm going to use it

thoughtfully and creatively, and we're going to make sure we have

good outcomes, and we're going to learn from the mistakes we

make, and we're going to hone it. We're going to share it with

our colleagues. We have other teachers who are not quite there

yet, which I also think is fine, and we are, as a school, working

to raise the floor for everyone so that AI is a real component.

Obviously, AI from a teacher perspective, as a teacher tool

is kind of incredible. It can really reduce the amount of time

it takes to do something we don't want it to reduce the

amount of thought or the amount of care or the amount of

understanding that someone has about what they are actually

doing. So it's really important to me, like on a personal and

professional level, that the AI isn't taking over our reasoning

skills, right? A teacher is still making the choices and

using AI to assist in the implementation of that choice.

But we would not look too kindly on someone just going to AI,

saying, write me a lesson plan for this, and then handing that

to the kids. You know, there might be a time when AI is so

good at mimicking the way we individually think that.

Something that it produces would actually be what I would

produce. But I'm not there at all. Like, I don't use AI to

write my own words. Almost ever the bio that I sent you all

beforehand, I wrote, and then I had aI write, and then I wrote,

and then I had aI write, and, like, we went back and forth,

and I was like, this sucks. Then I rewrote it, and that's what

you got, was the last piece of that chain. So those are, like,

the two big lenses we have, like for students, it's about, how do

you use it responsibly? And I'll tell you, it's really hard,

because kids are often teenagers who don't necessarily do what

you tell them to do, and so they may be using it in ways that we

don't want them to. Policing that is a challenge for

teachers, learning how to work around that has been a challenge

for us as a school. There's been an increase in in class work.

I'm going to watch you do something in front of me, and

part of me feels like that's a shame, but part of me realizes

that's a realistic response to the unknown situation of like,

how are kids actually completing the work that I'm assigning

them? And so we've been working really hard on giving teachers a

lot of toolboxes. I've been in the AI Council. I founded the AI

Council at the beginning. I've now handed it off to someone

else to run, but we are probably going to spin up an operations

AI Council in addition to the current academic AI Council, and

that's on my list for right now.

That's interesting. So you're going to

separate them, yeah, super interesting. Who serves on each

of those councils, and why did you decide to break them out?

So currently we have just the AI Council, and it

is basically division heads, me, assistant division heads, a

couple of teachers who are invested in this, and one other

person on my team, and our new director of studies, which is a

new position that we built this year, and the director of

studies and our Associate Director of Academic AI, which

is a position that reports to me that we made for last year. Are

running that council. It's very exciting like they're setting

the agenda, they're setting the conversation. They're bringing

topics to the table. We have built a system that basically

works. Now what we want to do is make sure that we are actually

working with individual teachers to make sure that we are

expressing that system appropriately. So Mattice, our

Associate Director of Academic AI, and Academic Technology

Specialist, is the one who is charged with going to all of our

middle upper school teachers and working with them hand in hand

to help them to figure out how AI can or cannot be used within

their own practice. Because our answer to things is not you must

use it. It's you must think about how you can use it and

make a reasonable decision, not you must do what we tell you to

do about all these things. The operational component is the

thing I want to build that I think should have me. I think

there'll be a couple of us who cross over, frankly, because I

think that's important to see the conversations on both sides.

But we have a pretty robust operations arm, like we have

admissions, we have development, we have finance, we have the

college office, which so much travels, academic and

operations. And there are a lot of places that we are not

currently using AI that I think would be valuable. And so I

think we need to start having those conversations more in

earnest. We started with the student facing part, because it

felt the most urgent from a community standpoint. And now I

think we need to move into the need to move into the what can

we do to enhance operations? I mean, like a tiny little

example, like, and you all go through this, like, the

scheduling of parent teacher conferences is really time

consuming. I sat down two weeks ago with one of our people who

schedules them, and just said, Show me the entire process. Like

I helped you build part of this years ago, but show me

everything. And as a result of that, I sat down, and this is

what I use a programmer for. I wrote a program that, with a

little spreadsheet and some inputs, will create all the

counter events, send all the emails to people, do all of the

things that were tedious before, but that's like a piece that AI

used, like I used AI to build that, and it would not have

existed without it. And we can use that in a million other

places, but people just don't know to ask the question. Ask

the question, or don't know that the resource is available. And I

think we need to get the word out problems small and large,

we're here for you

well, and also that you're doing it in a

really thoughtful and informed and aligned way. Because I think

that what's happening, or at least what I'm observing, is

that business offices are just going about their business and

figuring out AI, for example, without involving the tech team

and without making it a game plan, a strategy. So it's cool

that you're thinking about how you could do it in a more

comprehensive way, where everybody's sort of on the same

page.

That was actually part of the reason that I argued

for a title change for myself. I was a director of technology for

quite a few years, and before that was a, you know, slightly

different titles. And two years ago, we switched to me being the

Cheeto, the Chief Information Technology Officer, because I

wanted to make it really clear that I needed to have a seat at

all the tables, and that I needed to be involved, not to

tell everyone what to do, but to listen and to help. And you

know, we're still trying to make that come true, but that is why

I have the position that I do. Because we have a lens. US tech

folks have a lens across the whole school in a way that is

often very unique and not fully appreciated.

So as we start wrapping up, Jonathan, I

want to just give you a second to tell us a little bit about

some. The things you're thinking about, I would imagine that

we've covered some of that ground. But as you look at the

back half of the year, what are some of the projects or dreams

that you're dreaming in terms of things that you want to tackle

next?

Okay, I have so many things I want to tackle. I

use Asana, and I have a list that is literally so long that I

can't get to the end of it ever, which is scary, and often at the

same time, we need to go through a really huge operational review

of all of our HVAC systems, all of our security systems, and

bring everything under one consistent and clear umbrella.

And I have a really great new director of facilities and a new

director of security who are working on that with me. And

it's really exciting, because it's a place that we have so

much inefficiency that really, this isn't even an AI thing.

This is just, let's just get some money together and get some

planning together and start to bring everything under one

umbrella. Another big project I have is and I'm a little

embarrassed that I have let something go as long as I have,

but we have a lot of AV systems that are in place for too long

that need renovation, and so it just needs clear eyeballs. I got

a quote from our new vendor as of a year ago, but yesterday, to

renovate a whole bunch of systems, and it's super

expensive, so part of my job for the next like month is to

justify the very large requests for money I'm going to be making

this year in order to kind of catch us up a little bit. I'm

not a really big believer in everything has a defined

lifespan at the time of purchase. I don't want to tell

anyone that, like, you're due for a new laptop, because it's

four years old. I always say, like, is it fit to its purpose?

Like, does it do what it needs to do? It doesn't be flashing. I

don't use the newest. I don't use the latest and greatest. But

if you need that, that's what we're going to get you, because

that's what you need to be productive. And so it's hard for

me with our budgeting process. Like, a lot of boards want to

see leasing. They want to see every year an exact sunk cost.

We are more flexible than that. Sometimes the laptop last two

years, sometimes the last five years. So I'm going through all

of my budgets right now to figure out what that looks like,

so we can kind of have a better long term plan. But in terms of

AV, 10 years might be too long. Let's just say it out loud. So

we have some work to do. The other big thing that I want to

do is really support our Academic Technology team in

working with teachers, so they can really focus on bringing

technology to make better outcomes for kids. That is a

place that is, I think, really important. Well, it

sounds like you have plenty to keep you

occupied, and while I'm sure that there are many listeners

who are just drooling at the idea of how large your team is,

it sounds like you are keeping your hands full, that there's

always a big project. And isn't that just the case with

independent schools, there's always another project, no

matter how many sets of hands you have. So Dr, Jonathan King,

I'm so glad you joined us today. This has been so useful. We're

so grateful to have had this time with you, and we really

appreciate you joining us. Thank you. It was great to be here.

This has been talking technology with ATLIS,

produced by the Association of technology leaders in

independent schools. For more information about Atlas and

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