This startup added a new job app requirement for interns: handwritten cover letters

Even the companies promoting analog lifestyles are being inundated with AI job applications.

Dumb.co, a startup selling modified flip phones, was looking for interns passionate about being more offline.

There was just one glitch: A startling number of cover letters appeared to have been written by AI — or at least sounded like it.

The letters weren’t “connecting with our mission and our greater goal,” said Marlee Pelton-Fuentes, customer success manager at Dumb.co, who oversees the company’s internship program.

She discussed the problem with the company’s CEO, Danny Hogenkamp, as well as other coworkers.

To bypass the flood of cookie-cutter applications, they added an unusual requirement a few days after the listings went live: handwritten cover letters.

The company said that nearly 900 people applied to four internship roles — marketing, business and operations, customer success, and tech — through the job platform Handshake.

About 70% of those applicants uploaded handwritten letters answering why they were interested in “dumb living,” why they wanted to work at the company, and whether they had a “dumb” phone.

Another 200 to 300 applicants physically mailed their apps, including handwritten letters, said Afreka Ebanks, Dumb.co director of brand and communications.

After reviewing the notes and interviewing 60 people, the company hired 10 interns.

The prompts meant the letters felt more like personal reflections than rote formalities, said Pelton-Fuentes. “We were able to get a lot more about the person and the work that they want to do, their attitude, their passion.” At a time when job seekers are burned out from mass-applying and hiring managers are equally overwhelmed by the flood of applications, AI becomes increasingly used to ease the burden on both ends.

Cover letters — when they’re written at all — are often smoothed out or entirely written by AI.

On the hiring side, the tech is used to more quickly screen applications. “It’s basically AI selecting AI to elevate to humans for review,” said Judd Kessler, a professor of Business Economics and Public Policy at Wharton.

In this new reality, both employers and applicants have to find creative ways to stand out. “Anything that can break that equilibrium, that can inject more of real people showing their real selves to actually help employers find the right fit” is worth trying, he said.

Dumb.co hired Ian-Karlo Krockel as a marketing intern in July, a few months after he graduated from Boston University.

Despite feeling like a “very go-go-go kind of person,” he said he had no luck with job and internship applications until he applied to Dumb.co. “A lot of them just wouldn’t get back to me,” said Krockel, 21.

The Dumb.co application “was like a needle in a haystack,” he said.

Plus, it felt on-brand: A week prior, he had announced to his friends on Instagram that he was switching to a flip phone.

It was as if the mindset he’d cultivated over years around analog living had led up to this moment.

In his cover letter, he wrote about owning multiple flip phones and recently interning in London, where he enjoyed disconnecting from his smartphone and enjoying the city’s green spaces.

While the letter took him about an hour to write and scan, he said he felt reassured that at the very least, a real person would likely read it. “It felt like someone actually was looking through what I had to say and that it wasn’t just going through some sort of filtering software,” he said.

While reading hundreds of handwritten cover letters was more time-consuming than skimming typed submissions, Pelton-Fuentes said attracting interns who seemed genuinely engaged by Dumb.co’s mission made it easier to sort through the applications. “I was reading through more aligned applicants,” she said.

Plus, because she had to individually review each one, she said it made the interview process more personal; she remembered what each applicant wrote who made it to the next interview round.

For Krockel, it also made the hiring process more intimate.

He said he remembered Hogenkamp, the CEO, holding his letter and referencing it during his second-round interview. “It felt like I was very supported and going to be an actual part of the team,” he said.

As AI continues to reshape hiring, Kessler predicts that both companies and applicants will start looking for more old-school ways to assess interest, effort, and competence. “It’s one of these maybe counterintuitive outcomes — that the rise of AI is going to make the job market and the hiring process rely a lot more on human interaction,” he said. “We’re going to rely a lot more on people picking up the phone, calling potential connections, and asking them for help getting into the firms that really interest them.” He personally sees letters of recommendation holding more weight in the future, as they depend on positive working relationships.

Given how meaningful Krockel’s application experience with Dumb.co was, he hopes other companies will follow suit to cut through the AI slop. “Seeing what my friends have and are going through, and what I went through myself, it was just very bleak,” he said, adding that it meant a lot to know his application would be read by a human. “People my age want to work.

I just wish that more companies would make it simple to do this.”