"Silicon Valley has always been a long shot": Asana CEO Dan Rogers tells Gen Z to stop chasing shortcuts and build skills the hard way

In Silicon Valley, ambition sometimes arrives in unusual packaging. Founders have reported receiving donut boxes at their front desks, only to discover résumés tucked beneath the pastries.

The stunt, carried out by eager twenty-somethings hoping to break into the tech industry’s most coveted companies, reflects the desperation and creativity of a generation navigating layoffs, hiring freezes, and the looming shadow of artificial intelligence.But for Dan Rogers, the newly appointed chief executive of the $1.8 billion workflow software company Asana, the spectacle is less surprising than it might seem.

Silicon Valley, he says, has always been fiercely competitive.“I don’t remember it being easy back in the day, honestly,” Rogers 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.”

From Grimsby to Silicon Valley

Rogers’s journey into the heart of the global tech industry began far from the glass towers of San Francisco. Raised in the British town of Grimsby, better known in pop culture as the setting for a satirical film by Sacha Baron Cohen, he did not emerge from a traditional tech pipeline.Instead, his career unfolded across a series of influential roles at some of the world’s most recognizable technology companies, including Dell, Microsoft, Amazon Web Services, Salesforce, and ServiceNow.Each step added another layer of experience before ultimately carrying him to the Bay Area and the corner office at Asana.Today, Rogers occupies a position that allows him not only to shape the direction of a major software company but also to influence how the next generation enters the industry. Yet the advice he offers aspiring technologists is strikingly simple: stop searching for shortcuts.

The myth of the direct path

For many graduates, landing an entry-level role at companies like Apple, Meta, or Alphabet remains the ultimate goal.

But Rogers warns that such direct entry is rare.Rather than devising clever interview stunts or networking tricks, he urges young professionals to focus on building genuine expertise, even if that journey takes them far from Silicon Valley’s spotlight.“Maybe come into the side door instead of the front door,” Rogers advises. The strategy, he says, requires patience and a willingness to pursue opportunities that may initially seem less glamorous.“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.” The real advantage, Rogers argues, lies in accumulating meaningful experience wherever it can be found.“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 “donut box” of experience

Ironically, Rogers believes the true equivalent of that résumé-stuffed donut box is not a flashy stunt but a career built patiently over time. His own path offers proof. Before arriving in San Francisco, Rogers spent years building experience in roles across multiple regions in the United States.“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.”Those experiences, he suggests, eventually formed the professional toolkit that made him a compelling candidate for leadership roles in the Valley.In other words, the real “donut box” is not a clever résumé delivery, it is a portfolio of hard-earned skills.

Learning before earning

For students and young professionals, Rogers’s message carries a deeper lesson about how to approach the early stages of a career.“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.”In an era when social media often celebrates overnight success, Rogers offers a more grounded philosophy. Career capital, he says, must be built patiently, experience by experience.“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.”

A lesson for a new generation

For the many young professionals anxiously eyeing the tech industry, Rogers’s story reframes the pursuit of Silicon Valley success.The path may not begin with a coveted job offer from a global giant. It may begin in smaller companies, in different cities, or in roles that quietly develop critical skills.But those experiences, stacked patiently over time, can become the foundation of a career that eventually reaches the industry’s highest ranks.And if Rogers’s journey from a small English town to the helm of Asana proves anything, it is that the road to Silicon Valley rarely runs through the front door. More often, it winds through the side entrances, where persistence, learning, and patience ultimately open the way.