Cry ’til you laugh: Chris Pirillo vibe writes his job-hunting frustrations into brutally honest apps

At a time when finding a job in tech has become a frustrating cycle of rejection, ghosting or worse, Chris Pirillo’s work speaks for itself – because it makes fun of the whole process.

Pirillo, a long-time technology enthusiast and entrepreneur, has been showing off his skills by showing how difficult it is to get anyone to pay attention to his skills. His two latest products with vibe code include a Resume Analyzer and a rejection letter generator called Dear Applicant.

Each is sure to hit home with job seekers facing a seemingly hopeless process, as well as employers and employers hoping to fill roles with some human frame.

The Resume Analyzer is exactly what it sounds like – and it’s not what you might hope. Users are invited to attach a job description and upload their CV through what is billed as a “semantic scan” that produces a “personalised, actionable gap analysis report.” Of course, the punchline is that no matter what you submit, the verdict is the same: “Nah, f**ked, dude.”

Pirillo said the idea started as a joke on social media earlier this week. The response was quick and strong enough to convince him that the joke was actually a mirror. A few hours later, the app was live.

The Dear Applicant Generator came after that, born out of a comment in Threads suggesting the next logical step: a rejection letter that arrives before you apply. “Think of all the benefits of efficiency,” the analyst wrote. Pirillo obliged.

I checked both and left laughing both times, especially at the well-written method in Resume Analyzer, which read, in part: “No CVs were analyzed in the production of this report. No data was left on your browser. The job market is, in fact, a flaming garbage dump. This tool confirms what you already suspected. Have you ever considered raising goats?”

“These apps are funny because they’re not,” Pirillo told GeekWire via email.

A frustrated Pirillo is well documented – and the timing is no coincidence. A report last month by the pre-employment screening company Criteria found that more than half of job seekers had been harassed by an employer in the past year, a three-year high. It comes at a time when tech layoffs remain brutal: more than 178,000 tech workers will be laid off in 2025 alone, flooding an already troubled job market with qualified people competing for fewer positions — and hearing nothing.

The tension — between the gag and the real complaint underneath it — is what gives both tools their edge. Pirillo, who describes himself as someone who is more than qualified for the positions he is applying for, said he has stopped looking for work traditionally in favor of fractional and contract work, not because he wants to, but because someone feels like he is crying.

“That behavior and expectation has become normal,” he said of employer ghosts. “It’s a whole process by which a few of us control abusive people.”

Creating applications, he noted, took less than an hour each — a stark contrast to the hours job seekers often put into resumes and cover letters that often disappear without acknowledgment. Pirillo has now posted over 300 of these “mini-products” on his Vibe Arcade website and is actively teaching others, techies and non-techies alike, to do the same.

The question he asks is whether building things is now a better use of a job seeker’s time than applying for jobs. For him, the answer is yes — and he relies on what he calls an emerging archetype: the “product developer,” someone who shows off his work rather than choosing to continue.

“I believe I put more thought into making these applications than any company in processing my application,” he said. “Probably more than all of them combined — even when someone has passed on a hiring manager.”

He’s even considering attaching Dear Applicant’s advance rejection letter to his future applications – partly as a test, because he says he has nothing to lose.

“The worst thing that could happen is that I don’t get treated differently,” she said.

Pirillo doesn’t pretend the apps are a secret — or that they’ll change anything. You know HR won’t find it funny. But that’s not really who he’s talking to.

“If there was a purpose with these particular apps, it’s not just to revive the feeling of ‘you’re not alone’ but to laugh at the absurdity of the situation some of us find ourselves forced into,” he said.

Previously: Vibe-coding is the new reality: Chris Pirillo on the rise of AI-powered apps, features, and inventors