Jason Douglas `00 Got in Early on Laptops, Now He’s Helping Shape Artificial Intelligence

Artificial intelligence (AI) might be the hottest topic of conversation in the past decade, with no sign of slowing down. For Jason Douglas ’00, it’s just the latest in a series of major technological shifts he has experienced firsthand. He attended Country Day just as the school was instituting the nation’s first one-to-one laptop program, and he and his friends quickly became enamored with the machines.

“Country Day encouraged us to pursue our interests in computers,” says Jason. “For me, it eventually shifted toward using technology as a tool for science. Mrs. [Paula] Butler was my mentor for the Intel Science and Engineering Fair my junior year, where I won first place. I took something I was good at – computers – and combined it with something new to me: molecular biology.”

Jason went on to attend Harvard University, where he double majored in computer science and economics. Later, while working at Apple, he found himself in the “right place at the right time.” The first iPhone had just been released, giving him the opportunity to work on the first iteration of the App Store, back when not many people even knew what an app was. He also contributed to the first version of Apple’s AI assistant, Siri.

“While technology is always changing, you don’t often get to be part of a major societal shift in technological history,” says Jason.

Jason and his wife, Freya, celebrate their son Winston’s `31 second-place finish at the 2026 Power of the Pen regional competition.

Now a member of the technical staff at OpenAI (a company that isn’t big on titles), Jason works daily on projects that help companies enter the world of AI and explore how it can improve their businesses. Just as he witnessed a major technological shift at Apple, he sees similar patterns emerging with AI.

“AI is still evolving and is in the early, maybe even middle, stages of what’s possible. It’s another tool, like the internet and the mobile phone, tools that came with a lot of fear. But with those technologies, we learned how they could become indispensable parts of everyday life. AI is going to change how we do things, and we need to make sure we steer it in a positive direction.”

So, with new technologies evolving faster than ever, what advice does Jason have for students interested in pursuing a career in tech or computer programming?

“My biggest piece of advice is not to focus too much on a specific career path or worry about taking the ‘right’ courses. Find a personal project you’re passionate about and figure out how to use technology to support it. That’s how you’ll learn whether you truly enjoy it. There are so many tools available now, and it’s easier than ever to explore your interests and build something meaningful.”

Jason has one final piece of advice for Country Day students:

“Try different things. I feel lucky to have tried – and failed at – many things at Country Day. This is a unique opportunity to explore a wide range of interests. Many of my experiences have stayed with me, from playing sports, even though I wasn’t the most athletic, to writing for The Scroll for many years, to participating in Math Olympiad. You may not get another chance to try so many different things later in life, so take advantage of it now.”