September 2022 Alum of the Month: Sean Heywood ’96 ’96

SEAN HEYWOOD ’96 began his journey to Hotchkiss from only 100 miles south of Lakeville, but for him, the working-class neighborhood of Bushwick, Brooklyn, was a world away. Now a director of growth at Meta (formerly Facebook), he credits his Hotchkiss experience with preparing him for a career in leadership positions at several of America’s top technology companies.

Heywood came to Hotchkiss through the Albert G. Oliver Program, which places high-achieving Black and Latino students from New York City at top New England independent schools. “Despite some initial challenges, my time there was unambiguously valuable. It was the first time that I encountered students who looked like me and would go on to attend prestigious universities. That representation was transformative as it transitioned my academic pursuits from what felt like a walk of faith to one that was about execution.”

After Hotchkiss, he went to Brown University for pre-med. “But it wasn’t for me. I overheard some students talking about investment banking and changed course to business economics. I spent junior year at the London School of Economics and interned at Morgan Stanley sophomore and junior years.” He graduated from Brown magna cum laude and then received his M.B.A. from Stanford Graduate School of Business.

Heywood worked as an analyst prior to joining Google as a market manager. He went to Meta to lead strategic product partnerships for its Messenger app, cultivating its developer ecosystem as the app grew from 300 million to 1.2 billion users.

Moving to Amazon, he led Alexa’s business development initiatives involving the interoperability of Alexa with other artificial intelligence platforms. Heywood also led business development for Amazon’s

Surface Transportation group, where he focused on autonomous driving technology, alternative fuels and infrastructure, telematics, and fleet acquisition initiatives.

Having recently returned to Meta for new opportunities, he notes: “Meta’s mission to make the world more open and connected has always resonated with me. The work is sophisticated, global in scope, and quite often controversial. The scale at which we operate is non-intuitive and can be humbling. It’s my hope that my perspective and experiences can help influence the company through the next chapter of its growth.”

Heywood lives in Palo Alto, CA, with his wife, Kuleni Gebisa, and their three sons. “I met my wife shortly after college. We had our third date at Hotchkiss for Blue and White Weekend!”

His connection to Hotchkiss is strong. “Several faculty members were very influential for me, including Walter Crain, Patricia Redd Johnson, and Christina Cooper,” he says. “Along with others, they created a sense of home in an unfamiliar place, helping me identify and further develop my unique strengths.

“At Hotchkiss, I began to cultivate deep relationships with classmates who remain among my closest friends nearly three decades later, and met some remarkable people who left an indelible mark. At the recent wedding of Keith Bernard ’95, I reconnected with Ivan Henderson ’95, Tom Terbell ’95, Steven Turner ’94, and John Khoury ’95. It was an amazing time and a blessing to reflect on the experiences we shared decades ago. I’m also a member of a vibrant WhatsApp group with more than 60 Black and Latino Hotchkiss alumni. I’ve had the opportunity to work with several classmates over the years.”

Heywood hopes that Hotchkiss plays a role in determining the future of technology by shaping the next generation of leaders. “A decade is a lifetime in technology. The only certainty is that the scope of invention will remain unpredictable, and navigating how these technologies illuminate and amplify the best and more challenging aspects of humanity will become increasingly complex. This will require leaders who possess tremendous intelligence and a sense of empathy in order to safely shepherd these effects across our society.”

In closing, Heywood says, “I left a community where fewer than five percent of residents had a college education, and joined one where I could record the Brandenburg Concertos as a violinist, win two New England tennis championships, speak with Rosa Parks, and gain admittance to an Ivy League university. Hotchkiss, for me, created a paradigm shift in the trajectory of my life that will have generational impact. It was hard, but worth it.” H