Stephen Gillett: Leveling Up

There’s a land called Azeroth that isn’t real, yet it has millions of real visitors every day. Its currency isn’t real either, but as recently as August each digital token used to purchase Azerothian gold was worth more than the Venezuelan bolívar.

In this land, you can make more errors than the ’63 Mets and still come out on top. Why? Because it’s part of an online video game called World of Warcraft, and the cost of failure is far outweighed by its value: experiential learning.

Alumnus Stephen Gillett undoubtedly made thousands of mistakes in his ascension to the elite of Warcraft—mistakes, if made in the “real” world, that might have slowed his dramatic career progression.

World of Warcraft—or WoW—is a role-playing game that revolves around exploring exotic landscapes, fighting monsters, completing quests, and interacting with characters or some of the game’s millions of other players.

A 2006 Wired article credited Gillett’s WoW experience for giving him an edge when he applied for a senior leadership position at Yahoo! By then, Gillett had distinguished himself in this fantasy world filled with orcs, dwarves, and the undead. He had become a “guild master”—that is, a leader of a group of players, with administrative control over operations and the authority to give ranks or privileges and to add or remove members.

As such, Gillett had learned many of the same leadership skills he’d need in the new role with Yahoo!—like recruiting, communicating across language barriers, and dispute resolution. He now advises high-achieving gamers to list online achievements on their résumé—the geek equivalent of street cred.

“Gaming created a platform that allowed me to experience and refine skills in the online gaming world, long before I encountered them as a business leader,” he says.

Gillett served in a variety of leadership roles throughout the early 2000s, including stints at Best Buy, the security software company Symantec, and Starbucks (where he was selected by Fortune for its “40 under 40” list of young movers and shakers, partly for helping bring free WiFi to the coffee giant).

Since 2016, he’s worked for X, the “moonshot” division of Google’s parent company, Alphabet. X exists to transform innovative ideas into viable businesses—in other words, to create the next Google.

The process goes something like this: find a seemingly intractable problem, propose a solution just this side of ludicrous, and see if current or emerging technology could make it feasible. Then, ask some of the tech world’s most agile minds—what X calls “the rapid eval team”—to tell you why it won’t work. Bringing the internet to remote areas, for example. The proposed solution: create an aerial wireless network with technology in balloons hovering at 70,000 feet, an idea that survived the vetting process and is being tested in New Zealand.

Getting shot down early and often is exactly the point. The road to an ironclad idea isn’t paved with flawed ones—it’s the understanding of why they were flawed. In fact, employees are rewarded for filling ideas full of holes because it’s cheaper than sinking money into something that won’t pan out. It encourages the kind of innovative but pragmatic thinking that distinguishes world-changing companies like Google from all the rest.

Gillett’s been part of the process and says it’s as awe-inspiring as you’d expect.

“You realize quickly that the problems these teams are working on are very hard ones to solve and require a fortitude and sense of invention that is humbling to witness,” he says.

Ideas that survive the rapid-eval process may graduate into businesses under the Alphabet umbrella. The problem of cybersecurity, for example, led to the realization that underresourced IT teams have the tools to identify security issues—but not to prioritize them. Chase the wrong rabbits and potentially major problems slip through the cracks.

That idea became Chronicle, a cybersecurity company that launched earlier this year with Gillett as the CEO. The company will sell antihacking software to Fortune 500 companies, using “machine learning”—a type of artificial intelligence—to detect cyberthreats more quickly and precisely than is possible with traditional methods, Reuters reported.

According to Gillett, it’s not uncommon for hackers to go undetected for months, or for a company’s security team to take months to fully understand what’s going on once they’ve detected an issue. The result is more data breaches, more damage, and higher security costs.

“We want to [accelerate] the speed and impact of security teams’ work by making it much easier, faster, and more cost-effective for them to capture and analyze security [threats],” says Gillett, in a recent story for “We are building our intelligence and analytics platform to solve this problem.”

Alphabet’s backing aside, Chronicle is still a startup. Mistakes will be made, and employees will need to roll with the punches. Success will hinge on adapting to unforeseen challenges, thinking creatively about solutions, and communicating everything to the team in a way that builds not just understanding, but confidence.

Gillett, who graduated in 1998, says that’s where his liberal arts education comes in. Although he has fond memories of his gridiron days as an offensive guard for the Ducks, Gillett says choosing political science for his major was the smartest play of all.

For one, that discipline grounded Gillett in a plethora of topics that would quickly become important for the ambitious young climber in the tech world. “As I started to get up in the ranks of corporate America, I started to deal with public policy, NAFTA trade agreements, the western European financial crisis,” Gillett says. “All of a sudden, all of the studies I did as an undergraduate really became relevant.”

Even more importantly, political science captures the idea that politics—at least in theory—involves compromise and the appreciation of different views, cultures, and priorities.

“[My] liberal arts education provided a multifaceted view of the different perspectives in the world,” Gillett says. “It teaches an individual to use reason and logic versus pure emotion, which leads to productive conversations and creative problem-solving.”

Reason and logic vs. pure emotion may seem like an unfair fight in these times of rancor and absolutism. But undergrads should be heartened to know that, in the business world, rationality still has the edge. You can’t build a business case with opinions.

For students hoping to follow in Gillett’s footsteps, he has some advice: be deliberate. Make the most of your time. Learn a second language. Explore the far reaches of what the UO has to offer.

“My advice centers around students both making a living and making a life,” he says. “Their education and degree focus should enable both of these to be realized.”

—By Cody Pinkston

Cody Pinkston is an author and videographer who lives in Bend with his wife, Amy. His genetic-engineering novel, The Perfect Generation, is now available on Amazon.