Getting a job in Silicon Valley is so cutthroat that some ambitious unemployed twenty‑somethings are literally hand‑delivering donut boxes stuffed with their résumés to founders’ front desks, hoping it will make them stand out for the hottest tech roles. But that’s nothing new, says Dan Rogers, the new CEO of the $1.8 billion workflow software company Asana.
Although Gen Zers are facing layoffs, hiring freezes, and AI anxiety at an unprecedented rate, landing a job at the HQs of Apple, Meta, and Alphabet “has always been a long shot,” Rogers warns.
He would know: Rogers is one of the few British Silicon Valley CEOs. He started out in the small town of Grimsby—better known as the butt of a Sacha Baron Cohen movie than as a tech launchpad—and worked his way up to the top job in San Francisco via stints at Dell, Microsoft, Amazon Web Services, Salesforce, ServiceNow, and more.
“I don’t remember it being easy back in the day, honestly,” he exclusively tells Fortune of breaking into Silicon Valley. “For me, for example, it was never going to be possible that I’d go straight to the hottest tech company in the hottest role. I always felt like I was going to have to work my way in, and I was going to have to work through experiences elsewhere that I would shine at.”
And now that Rogers is in the prime position of hiring and shaping the Bay Area’s workforce, he says that’s still the case.” Despite the explosion of AI creating more tech jobs, competition for those entry-level roles is just as hard.
Asana CEO’s advice for Gen Z looking to land jobs in Silicon Valley
Ask Rogers for advice on the next generation trying to crack California’s tech scene, and he doesn’t have a quick hiring hack or an interview stunt.
Instead, he recommends quietly building a résumé that’s impossible to ignore—even if it takes years and detours through less prestigious companies. Or as he put it: “Maybe come into the side door instead of the front door.”
Rogers stresses that landing an entry-level job, internship or grad scheme directly at one of after graduating “is a long shot.” Not impossible, but unlikely. For most Gen Zers, he says, the best route in is to build credible experience somewhere that’ll teach you the tech skills the big names will eventually want.
“For those of us that go don’t get through the front door, it’s okay,” he adds. “There are side doors along the way, and you’ve just got to build towards that.”
“There are incredible experiences that you can get, maybe in smaller companies, maybe in a slightly different region, maybe in a slightly adjacent category. After a stint there, you would be super valuable.”
The mindset hack that’ll eventually lead to Silicon Valley success—or rather, his version of the donut box
Rogers is proof that a rejection letter from your dream tech company isn’t the end. He too, had to work his way up the ranks through “side doors” to get to where he is today. “My story ends in Silicon Valley,” he says. “But in the interim, I did really important roles in Texas. I did really important roles in Seattle, etc.”
By the time he finally made it to San Francisco, he’d stacked enough varied experience that he could pull from a deep toolkit—what he jokingly calls his “donut box” version of presenting himself to tech bosses.
Ultimately, if you chip away at building skills in your twenties, the salary and title will come later. It’s slower than a literal donut box stunt (or even shooting bosses’ cold emails, or wearing a placard sign asking for work), but far more reliable.
“I once received some advice from someone, and they said learning before earning,” he adds. “You should make sure that the learning phase of your career extends as long as possible before you even think about the earning phase.”
“What that really meant for me was there’s no shortcut to putting the building blocks in place that you’re going to need to be successful.”
