September 2022 Alum of the Month: Sean Heywood ’96
Hotchkiss | Sean Heywood '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 underserved New York City communities at top independent schools throughout New England. “Despite some initial challenges assimilating to the ethos of Hotchkiss, my time there was unambiguously valuable. It was the first time that I encountered students who looked like me and came from similar communities who would go on to attend prestigious universities. That representation was transformative for me as it transitioned my academic pursuits from what felt like a walk of faith to one that was primarily about execution. I knew that I’d be good if I could make it through all four years.”

After Hotchkiss, he went on to Brown University with the hope of becoming a surgeon. “But pre-med wasn’t for me. Organic chemistry won that battle, and I needed to pivot. I overheard some older students talking about investment banking, and I changed course to business economics. I fell in love academically and ended up spending my junior year at the London School of Economics and interning at Morgan Stanley my 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 at Morgan Stanley and McKinsey & Company prior to joining Google as a market manager. He then 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: “The company's mission to make the world more open and connected has always resonated with me as a user and former small-business owner. The work is sophisticated, global in scope, and quite often controversial. The scale at which we operate is non-intuitive and can be incredibly 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 in Brooklyn shortly after college. We had our third date at Hotchkiss for Blue and White Weekend!”

That connection to Hotchkiss is strong for Heywood. “Several Hotchkiss faculty members were very influential for me, including Walter Crain, Patricia Redd Johnson, and Christina Cooper,” he says. “Along with other phenomenal educators, administrators, and coaches, they created a sense of home in a very unfamiliar place, helping me identify and further develop my unique strengths in an incredibly competitive arena.”

In retrospect, Heywood says, “Hotchkiss is where I began to cultivate deep relationships with a handful of classmates who remain among my closest friends nearly three decades later. I met some really remarkable people in Lakeville who left an indelible mark. I recently attended the wedding of Keith Bernard ’95 and got to reconnect 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 memories and experiences we shared decades ago. I'm also a member of a vibrant WhatsApp group with more than 60 Black and Latino Hotchkiss alumni from the 1990s. I’ve had the opportunity to study and work with several Hotchkiss classmates over the years.”

Heywood hopes that Hotchkiss can play 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. New challenges will require leaders who possess tremendous intelligence and a sense of empathy in order to safely shepherd the effects of these technologies 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, have an opportunity to 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 it was worth it.”

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