Why this CIO plans to incorporate AI into his edtech wheelhouse

"If you choose to respond in a powerful, informed, instructive and positive way, then it can be a huge benefit for us," says Jon Ostendorf, CIO at the Princeton Day School. "It's exciting because it's a challenge and we have to respond to it right away. Every day, you see more potential."

Despite how prevalent it’s become over the past several years, edtech isn’t the sole driver for student learning and instruction. It never has been, says this chief information officer. It’s there to meet a need, whatever that may be. But to say edtech hasn’t evolved is a misconception.

Jon Ostendorf, chief information officer at the Princeton Day School, a private coeducational day school located in Princeton, New Jersey, says technology is there to support whatever the teacher needs, regardless of the subject.

“We’re able to have a good, solid infrastructure and 1:1 learning for our students,” he says. “We try to support whatever teachers need. If the ceramics teacher likes to have an app for designing ceramics on iPads, we do that. I think this is a school where technology is well-integrated and we support what the school is trying to do.”

But Ostendorf doesn’t understate edtech’s use in the classroom. He found that, as technology becomes more reliable, especially for teachers, it will be used even more frequently in the classroom.

“It’s more ubiquitous in the teaching and learning as you walk through the halls,” says Ostendorf. “You see it everywhere.”

Ostendorf became PDS’ first-ever CIO in 2014, a unique experience that he says has helped the school achieve growth.

“I have a really good team here that was operating without me,” he says. “I think it helped a lot to have the structure of having a CIO in place to build some of these values with the team where we’re not satisfied with not being absolutely ready on the first day of school.”

In the time he’s been there, he says they’ve switched out nearly every important system that they had, including email, a new learning management system, and a student information stem, among others.

“It’s all been strategic, not knee-jerk,” he says. “Then also, having that connection between leadership and the technology department, I think, has been really good.”

The evolution of the CIO

The pandemic certainly drove the transformation of edtech, he notes. But over the course of his career, Ostendorf has seen the job itself undergo change.

Ostendorf has worked in the education sector since 2000, where he served as the IT director for the Charleston County School District in South Carolina.

“At this point, I probably have more years in this role than almost anyone in it,” he chuckles. “I’ve really seen the role evolve as technology has become vital. It used to be plan B. You’d use a little technology here and there to supplement what’s going on. And then it became plan A, but you still had a lot of other things to fall back on.”

Now, every day, technology is plan A, he says. And if the technology fails, “you’re losing tons of instructional time.” And because of this evolution of edtech, so, too, has the role of the CIO.

Nowadays, he says the job also requires a very strategic person who can see the big picture and help point their team in the right direction. Additionally, it demands critical thinking surrounding security, an issue that has always existed but is now crucial for leaders to grasp.

With the exception of large, resource-rich school districts, that responsibility tends to fall on the CIO or technology director, he says.

“It’s always been sort of important, and it’s just grown and grown,” he says. “Schools have always liked to sort of err on the side of freedom and try not to worry about security if it’s not convenient. We’re in an environment now where you can’t ignore it anymore. But it’s important that you allow the creativity and accessibility that you need along with the security.”


More from DA: How ongoing turnover at the top is impacting superintendent salaries and bonuses


The role also changed for a brief period during the pandemic, he says. During this time, PDS was fully hybrid, so each student could decide whether they wanted to come to school or learn at home each day with the promise of an experience of equal quality to on-site learning.

“It put a lot of pressure on getting the right technologies and making sure everything was running smoothly since each teacher had to be teaching a mixed class of on-site and remote students,” he says. “Preparation was intense, and then I put many miles on my fitness app every school day checking on classrooms and making sure everything was going well.”

Summer preparation

For students, the last day of school marks the beginning of a well-earned summer break. For leaders like Ostendorf, it’s the first day of preparation to ensure students are running at the same pace they left off.

“We really commit to just being ready for the first day of school where there aren’t a lot of growing pains during the first couple weeks of school,” he says.

For instance, all of their lower and middle school students use school-issued iPads. It’s up to Ostendorf and his team to make sure they’re prepped with everything the student needs on day one.

“The first time teachers want to use iPads in class, they just use them,” he says. “We are really proud of that.”

His time will also be spent comparing their acceptable-use policies, prepping equipment for new employees, and updating network security, among other responsibilities.

Why he’s excited for 2023-24

Like many other technology experts who truly understand its potential to enhance learning, Ostendorf says he’s looking forward to finding creative ways to integrate generative artificial intelligence tools, like ChatGPT, into the classroom.

He says AI is simply different. As someone who was around to experience the integration of the internet and computers in the classroom, Ostendorf believes generative AI is demanding an immediate response from leaders and teachers because it is truly a disruptive force.

“You hear that term used a lot. It’s almost a cliché,” he says. “But it really is disruptive. And with the generative AI, it was just suddenly there. And it worked. All of a sudden it could be used for all these different things, both good and bad.”

Ostendorf believes that it’s up to us to choose how we respond to the technology.

“If you choose to respond in a powerful, informed, instructive and positive way, then it can be a huge benefit for us,” he says. “It’s exciting because it’s a challenge and we have to respond to it right away. Every day, you see more potential.”

As for its use in PDS, he says he’s optimistic that it will have a great impact on student learning, as long as there are safeguards in place.

“What we think is important is for teachers to understand what it can do and for us to give them some strategies for using it,” he says. “We’ve started that already and we’ll be focusing more in the summer on how we do that. But I’m absolutely convinced that it can be a positive thing.”

Micah Ward
Micah Wardhttps://districtadministration.com
Micah Ward is a District Administration staff writer. He recently earned his master’s degree in Journalism at the University of Alabama. He spent his time during graduate school working on his master’s thesis. He’s also a self-taught guitarist who loves playing folk-style music.

Most Popular