Chieh Huang has seen disruption cycles before. As co-founder of Boxed (the bulk shopping app that went public via SPAC), he built a company that employed thousands of warehouse workers. Now he’s betting that AI will trigger the biggest workforce transition in a generation. And he just launched Pelgo to help people land on the other side of it.
We sat down with Chieh right after Pelgo’s launch to talk about:
- What’s coming
- Who’s most at risk
- And why the scariest part isn’t the jobs that disappear
Scroll down to watch the full conversation (or keep reading for the highlights) 👇
The ‘First Rung’ Problem
Pelgo wants to be the infrastructure that makes AI-driven job transitions less painful. Because right now, almost nobody else is building it. As Chieh told us:
“There’s so many companies that are well-funded that are producing technology that will eventually take people’s jobs. But there’s very few companies saying, okay, how do we train these folks or how do we get them ready so that we’re not all just sitting on a couch collecting UBI checks?”
The early signal from Pelgo’s customer discovery is telling … and a little unsettling. The most forward-thinking companies reaching out are tech companies. And the roles they’re looking to eliminate aren’t senior positions.
“The roles being eliminated or the roles that they’re looking to eliminate, unfortunately, are a lot of the junior ranks.”
That creates a downstream problem nobody’s really talking about yet:
“Like, John, me and you, we probably went to the office every day when we started our careers, and [learned] through mentorship… but if that first rung isn’t there to start your career, I think that poses a really big question and problem for society.”
Where does the next generation start if the entry-level jobs that used to teach you the business no longer exist? Its a serious question that remains unanswered.
The Cognizant Playbook
Chieh’s co-founder brings a background from the world of systems integrators, as he had previously founded one of the largest SIs in the world, Cognizant. That’s not a coincidence. Chieh sees a direct historical parallel between what happened with outsourcing and what’s about to happen with AI:
“Cognizant started off as a company … that helped folks outsource jobs in India because of this thing that was invented called the Internet. You no longer need to be physically planted on site in order to do your job.”
Did outsourcing cause job loss in the US and other Western countries? Probably. But the Internet also created entirely new categories that nobody could have predicted. As Chieh said:
“In the 90s, when a lot of these companies started, who knew what social media was? Who knew that content moderation was a thing? But here we are 20 plus years later, it’s a huge business.”
The bet is that AI follows a similar trajectory—just compressed. Maybe dramatically compressed.
“We do believe that AI will follow a similar trajectory, maybe just way more compact than 20 years.”
Venture5’s Take
The AI job displacement conversation tends to go one of two directions: utopian (“new jobs will magically appear”) or dystopian (“we’re all doomed”). Chieh is carving out a more pragmatic middle. Yes, jobs will be destroyed, yes, new ones will emerge, but somebody has to actually build the bridge between those two realities. That’s what makes Pelgo interesting to watch. The question is whether the transition happens in 20 years or 2.
The full conversation went a lot of places we couldn’t fit here, including vibe coding and what it reveals about the SaaS meltdown, the rise of forward-deployed engineering, and yes, what it’s like sitting on the board of Six Flags. Watch the full interview above.
