In a sunlit Senior School classroom, Eben Adams ’89 P’26,’29 stood in front of a group of curious students, guiding a discussion about whether AI should be allowed to diagnose medical conditions. For Adams, it was a full-circle moment — bringing his professional passion for artificial intelligence back to where his love of learning began.

Adams arrived at Shady Side Academy as a third grade student in 1978, never imagining a world shaped by AI — let alone his role in shaping it for others. But Shady Side’s emphasis on exploration and growth gave Adams his first push to embrace the world beyond his comfort zone. 

As a child, Adams longed to play on a baseball team but never had the courage to try — until he came to Shady Side. “I was always so scared to do it. But at Shady Side, I felt like I could, and I loved it,” Adams says.

Adams fondly recalls carrying a cherished baseball glove through the Middle School halls — until his name was unexpectedly called to the head’s office. Fearing trouble, he was surprised when Head of Middle School David Mancosh handed him a wood engraving pen to mark it with his initials. “It has always stayed with me how thoughtful that was,” Adams says.

It’s that spirit of care — combined with a culture of curiosity and perseverance — that Adams credits with preparing him for a world in constant motion.

After earning a bachelor’s degree ,  and later an M.B.A.,  from Carnegie Mellon University, Adams gravitated toward work environments that mirrored Shady Side’s emphasis on open-ended inquiry. He joined FreeMarkets, a pioneering digital startup where he gained a firsthand view of entrepreneurial thinking. “It was such an amazing group of people — super talented and so forward-thinking. It broadened my entire perspective on what professionalism looks like,” he says.

He continued to build his expertise in business development at several Pittsburgh-based companies before joining LegalSifter, where he now serves as Vice President of Enterprise Growth. His role — at the intersection of AI and contract operations — feels like the natural next chapter in a career fueled by curiosity.

“My experience at LegalSifter has been transformational . It’s where the practical applications of AI really came to life for me,” Adams explains. “There’s a lot of creativity in trying to figure out how we can use AI to impact people’s daily lives.”

In 2018, long before ChatGPT became a household name, Adams helped organize a Shady Side panel on AI’s growing impact — bringing together alumni and experts to discuss how the technology was transforming business, education, and Pittsburgh itself. It wouldn’t be the last time he helped keep SSA on the cutting edge. 

This past spring, Adams co-taught the Senior School Immersive course AI Revolution: Shaping the Future of Society alongside English teacher J.A. MacDougall. They guided students through AI’s history, its impact in fields like healthcare and finance, and the ethical questions it raises.

For Adams, it was more than a chance to give back —  it was a window into how today’s students are grappling with some of the most complex and consequential issues of our time.

More importantly, he used the class as a bridge — connecting students with professionals on the cutting edge of the field. Guest speakers included a Carnegie Mellon University professor, a University of Pittsburgh researcher, a venture capitalist, and a colleague from LegalSifter.

“It was powerful to see students ask deep, thoughtful questions — not just about how AI works, but about how it should work,” Adams says. “That’s the kind of critical thinking Shady Side nurtures.”

Adams’ teaching role is just the latest chapter in a long history of involvement with the Academy. He served as president of Alumni Council from 2008 to 2010 and as a member of the Board of Trustees from 2010 to 2015.

“My superpower is that I’m really good at seeing relationships where other people might not see them,” Adams says. During his tenure on the Board and Alumni Council, he channeled that ability into building stronger connections across the SSA alumni network.

Today, Adams is also a proud SSA parent, with two sons enrolled at the Senior School. “I’ve always felt a very strong allegiance to Shady Side,” he says. “I’ve valued the relationships I made here and the amazing experiences I had.”

He believes Shady Side instills a mindset that is both rare and enduring. “Every single person I know who went to Shady Side can engage with others and have thoughtful conversations about a wide range of topics in a way that is confident yet considerate,” he says.

As AI continues to reshape society, Adams plans to keep growing professionally — but knows Shady Side will remain a meaningful constant. “I’ve had these four distinct phases of my relationship with Shady Side,” he reflects. “As a student, an alum, a trustee, and now a parent. That kind of connection — it’s extraordinary.”