Asana CEO: Breaking into the Tech Sector has Never Been Easy

As organisations reduce their headcounts – with Challenger, Gray & Christmas reporting that companies announced over 54,000 AI-related layoffs in the US for 2025 – many entry level employees are concerned about the impact of AI on the workforce. 

According to research from EY, 41% of employees believe AI is evolving too quickly, and 65% say they are anxious that they will be replaced by AI. 

Dan Rogers, CEO of Asana, however, believes that workplace competitiveness has not increased in recent years. 

In an interview with Fortune he discussed his own career trajectory, saying: “I don’t remember it being easy back in the day, honestly.

“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.”

Human-centric AI

Dan joined Asana in mid 2025 as the company began to shift its focus to building an AI-driven platform. 

During his tenure, the company has launched AI teammates, which embeds autonomous agents within its operational framework to work alongside human teams. 

According to Dan, this technology allows agents to collaborate alongside human workers, instead of using AI to reduce headcount. 

Dan says: “Everyone is building autonomous agents, but autonomy is the wrong goal. Work is highly nuanced – enterprise workflows encompass many teams, multiple data points and impact all levels of the organisation. 

“Agents can only collaborate effectively with humans if they have access to the company’s operational framework or ‘blueprint’ to who is doing what by when, how and why.”

This model fits within the company’s human-centric approach to AI, which focuses on using AI to augment human capabilities and accelerating workflows. 

A more challenging work environment

While Dan believes the level of competitiveness entry level talent faces has not changed, Juan C Andrade, CEO of USAA, disagrees.

Discussing the workforce in an interview with Fortune, Juan said there has been “a lot of layoffs already across the economy”, and says that he thinks that “unfortunately, our Gen Z’s not going to be as well off as our boomers and Gen Xers were”. 

To manage this challenge, he believes younger workers need to invest more in their careers, saying: “Nobody cares about your career more than you do.

 “Other people can help open doors, but you’re the one that has to figure out what it is that you want to do with your life. What are you interested in? And don’t leave it for luck.”

Dan suggests younger employees take a similar approach – particularly those looking to break into the tech sector, which Dan says “has always been a long shot.”

“I once received some advice from someone, and they said learning before earning,” he says. “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.”