An Office in the Great Unknown
An Office in the Great Unknown

An Office in the Great Unknown

Hillbrook Alumni and Jobs of the Future

In 1965, Gordon Moore – the future cofounder of Intel – observed that computer chip transistors doubled about every two years. Plotted on a simple bar graph, Moore foresaw tech innovation as a staircase with no landing, a line sloping upward into an unknowable future far off the margins of any page. Though “Moore’s Law” has lately surpassed itself, its original postulate still holds true: the creative force of innovation is unstoppable.

As Head of School Mark Silver has said since he first arrived at Hillbrook in 2009, we are preparing children for a future we cannot yet imagine, and for jobs that do not yet exist. We see our students’ futures a lot like that chart: a line we’re drawing off the page in real time, trying to articulate a lesson now that will still make sense when we arrive. Put another way – how might the classroom experience of today provide the tools a student needs for an unknown tomorrow? For two of Hillbrook’s alumni, the answer is simple: the combination of math’s ability to discover a right answer with the soul-defining ability to take a risk – one of the four Core Values of our school, and perhaps the one with the longest reach. Where precision meets creativity is where innovation is born – and while catching up with Alejandro Wilcox (Class of ‘15) and Chris Hailey (Class of ‘13), we got an inside view into what it’s like to build a career – and a vision for a life – in a career field where the greatest possibilities exist somewhere off the page and in the great unknown.


Before attending Cornell and snagging a competitive internship at Tesla, Alejandro Wilcox was always interested in engineering, but even as a student at Hillbrook he never imagined what form his love of practical math would take. “Did I think I’d work in engineering? 100%,” he said. “When people asked me, what do you want to be when you grow up? I always said airplane engineer, because [at the time] that was the bleeding edge of technology…but did I think I’d be working on the craziest cars in the world? Not a chance.” He recalled his childhood interest in cars as more aesthetic than mechanical – he cited the McLaren F1 as a personal favorite – but his internship at Tesla has opened more engineering and creative doors than he’d ever thought possible. “I always knew that I wanted to be an engineer in some way or another – I’m ecstatic about where I am now and where I get to go in the future.”

As a chassis engineer, Alejandro’s internship involves “everything between the motor and the road. “I’m organizing and performing tests on specific bolts, joints, building out models for thermal expansion–all very much on the technical side of things,” he said. The role is a dynamic outlet for Alejandro’s engineering skills, with each day bringing new challenges, new discoveries, and new limits to break through. “[We’re working with] a revolutionized technology – as a legacy carmaker, you would have as much experience trying to make a hairbrush as you would trying to make an electric car. You have four doors, a windshield and four wheels – that’s about the only thing that’s the same. The fact that it is such a massively new technology is really exciting.” (An added bonus: “We get to drive around the cars that we’re putting these wild, wild (prototype) things on!”)

Although only a few months into his role, Alejandro has found his technical and engineering skills expanding by the day. “Engineering is a huge field, obviously – it’s everything from communication to running simulations, to doing some hard math, to figuring out what kind of tests you want to perform…it’s really great to get that kind of experience.” He has also found a thriving, supportive company culture that encourages ideas above all else. “There’s a lot of young people working together – and working with each other – constructively and critically to make something that has never existed before,” he said. “People are passionate about things, but pride never gets in the way of the best idea. And the best idea always wins.” 

Mechanics aside, Alejandro found that his growing knowledge about environmental issues has kept pace with his career trajectory. “When I first learned about Tesla, I didn’t even know that their whole goal was sustainability. I just saw some of the coolest, fastest cars in the world. And then I started learning more about where we are in global warming and the globe being alive…So all these pieces were falling perfectly into place.” He recalled a project from his Hillbrook middle school days that had a lasting impact: “In science class, we made a sustainable house design, where we had to build a model house that could get as warm as possible using [household materials] like cling wrap and styrofoam. I had to think about all the little stuff that goes into a building And that really got me thinking in a brand-new way – like, How can we do this the best way possible? How can I create a thing that works?

He remembers Hillbrook math teacher Robert Sears as a key influence on his path towards math and engineering. “Mr. Sears really made all of us think about how things work, and how we can make them work,” Alejandro said. “The math might be challenging, but once you get a correct answer, it’s just right. And then you can use your right answer to make something that works. That kind of inspiration really drove me through high school and college.​”

Robert remembers Alejandro fondly as well as one of the first students he ever taught at Hillbrook – and how Alejandro’s career trajectory aligned perfectly with the sharp, hardworking 7th grader he taught in 2014. “I remember the enthusiasm with which he would tackle challenging problems and his excitement over explaining his solutions,” Robert said. “He was also very supportive of his classmates. Alejandro really understood math as a process, and would push himself to articulate his thinking. His class was a great introduction to Hillbrook.”


Across the Valley, USC graduate Chris Hailey is making headway into the dynamic world of cryptocurrency as a software engineer at Coinbase. Cryptocurrency is, of course, something that was barely in its infancy when Chris was at Hillbrook. “My first college internship ever at a traditional bank – I learned a lot, but I had a feeling that [banking was] going to be progressing into the future,” he said. When he landed an internship at Coinbase, “I still wasn’t sure about cryptocurrency – I remember people going through the initial boom (and crash) in 2017 – and I still wasn’t sure if this whole decentralized thing was going to work. But then I got to learn all the different aspects of it – not just the buying and selling, but the underlying technology. And that’s when it started to click.” As an 8th-grader at Hillbrook, Chris had no idea he’d one day wind up working on the cutting edge of new financial technology. “I see it as a more exciting form of something I’ve wanted to do,” he said. “I started in traditional finance at a large bank, and I was able to transfer those skills over to crypto. You don’t necessarily have to start at the cutting edge to make a difference in a new field.”

Chris’s career journey into crypto gained momentum in his teens and early 20s – his international travels in particular illuminated the possibilities of futuristic finance. “I used to take a lot of trips to Asia before the pandemic, and saw that a lot of Asian countries were very forward-thinking with their mobile payments. I could buy vegetables from a street vendor or a local market – and instead of cash, I could just scan a QR code and pay through my phone. It was a revolutionary idea to me. Without a central credit system, people really used mobile payments as an opportunity to jump up.” The rest of the world is catching up quickly, however. “A lot of technological progress here happens when there is a crisis, so these past two years there have been a lot of experiments,” he said.

Though his job title at Coinbase is software engineer, Chris’s role is far from siloed – and the task-agnosticism keeps his days exciting and filled with new opportunities to learn, grow, and build on his knowledge and skill set. “I work cross-functionally with a lot of different teams – other engineers, product, design – and that’s something I’m really excited about. I get to understand the engineering systems and the business decisions that go with them, as well as why and how something was made in a particular way. I like to use the analogy of Google maps – I can zoom out and get a high-level overview, or zoom in to understand the details. I love having a holistic view of everything.” Chris hopes to use his knowledge to start his own company one day.

As with any cutting-edge space, crypto is divisive, and still evolving as its different capabilities (like NFTs) take shape. “We’re really in the wild west days,” Chris said. “With crypto, there are plenty of fans, but there’s also a lot of detractors.” As with all new industries, weeding out the scams and opportunists takes a keen eye and experience; there is also an issue with tribalism among the different available systems. “There are a lot of people who are Ethereum maximalists, who don’t agree with people in Bitcoin; Solana and Avalanche have their own little tribes as well. So there’s a lot of potential for the technology – but people in the industry have to start getting along!” Cryptocurrency is reckoning with its environmental impact, as well. “​​Some of the crypto coins still use this algorithm called proof of work, which does involve a lot of energy usage,” Chris explained. “But some of the new coins are moving to an algorithm called proof of stake, which does not involve having to mine these coins – they’re able to get faster transaction speeds [without using] as much energy.”

His take on working in a brand-new tech space lands somewhere between caution and confidence – a carefully optimistic approach borne of his wide array of background knowledge. “I wouldn’t say I’m a maximalist – I still think there is a place in this world for traditional finance for Fiat currencies,” he said. “But I do think new technologies and older technologies can coexist peacefully. With NFTs especially, we’re in a speculative market.”

“Chris stands out in my memory as a student whose curiosity, risk-taking, entrepreneurial spirit, and eagerness to make connections between things he was learning stood out to me as his middle school science teacher,” said Ilsa Dohmen, Director of Teaching and Learning. “He was always really excited to ask questions, had really big wonderings, and was excited to notice connections and discover concepts that crossed domains. It’s no surprise to me that he’s now taking on the world of cryptocurrency,”


When it comes to working in a brand-new industry, both Alejandro and Chris are only looking forward – with their Hillbrook experiences to guide them along the way, lighting the way further forward into the respective great unknowns of their career paths. “[Hillbrook] is a nurturing environment that helps people get the most confidence out of themselves,” Chris said. “It was that confidence – that ability for me to say, I can do anything – that helped me get to where I am today. Just the confidence that kids have here.”

“With math, there’s always one right answer. With [the future] there definitely isn’t – so it’s really up to me to choose,” Alejandro said. “I don’t have an exact plan of what I want to be doing, but that is what lets me sleep at night, knowing that there are so many possibilities. It’s worth finding the stuff to be excited about.” 

For today’s students the lesson could not be more clear – what they are learning now at Hillbrook is laying the foundation for jobs that we cannot even imagine. What’s the cryptocurrency of 2035? We know that our Hillbrook students will be prepared to lead the way.

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