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The Career Calamity

Two of the most prominent legacy job application sites file for Chapter 11 bankruptcy. Together. Maybe they lost their edge.

By Ernie SmithJune 25, 2025
https://static.tedium.co/uploads/trumpasaurus.gif
#jobs #career sites #monster.com #careerbuilder #internet history #mascots #advertising #linkedin #job sites

I’ve never gotten a job from Monster.com or CareerBuilder, but I know their names well. Both have been around as long as I’ve been on the internet—Monster, via its MonsterBoard predecessor site, founded in 1994, and CareerBuilder, since 1995. (A third jobs site founded in the ’90s, HotJobs, was integrated into Monster in 2011, so technically we have a third legacy at play.)

But I bet you when you think of getting a new job, you think of LinkedIn these days, or if you’re not thinking of LinkedIn, you’re considering Indeed or ZipRecruiter. Or maybe some weird AI startup.

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CareerBuilder, as it looked like around 2000. (Internet Archive)

Which perhaps explains why CareerBuilder and Monster announced their plan on Tuesday to enter Chapter 11 bankruptcy. The companies, which merged together last year, are essentially doing the court-supervised sale process to sell some existing assets (notably the news site Military.com) in the process of getting purchased by a jobs site targeted at shift workers, JobGet.

They’re not dead just yet, but it is an excellent sign of where things are headed with the job application market that these onetime giants have now been turned into third-tier players. What’s more, they’re getting bailed out by a firm that literally integrates a “do surveys and play games for money” feature into its app.

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What the hell are we even doing now that this isn’t the norm?

Most modern job apps are generally anonymous and worth forgetting, but you know one thing that isn’t? The Trumpasaurus. That is the name of the Monster originally at the center of Monster.com, a beast that has nothing to do with the current president. The mural that Phil Manker made of the various Monster characters? Just … chef’s kiss.

Of the two companies, Monster is immensely more interesting to me than CareerBuilder, which has largely carried itself as a professional jobs site pretty much throughout its history.

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The Monsterboard design, as it looked like in 1996. (Internet Archive)

It doesn’t look like much now, but Monster had some incredibly weird corporate branding for a website intended to make it easier for people to find jobs. It had a black website long before dark mode was popular with the public. Its corporate mascot looked like a DeviantArt original.

That’s not to say CareerBuilder didn’t have its moments of whimsy. The company was well-known for a popular series of Super Bowl ads in the mid-2000s that put monkeys in an office.

But these brands struggled to stick the landing. CareerBuilder, which was long operated as a joint venture of the major newspaper chains Knight Ridder and Tribune, had to carry those all that cruft on its back. (It was eventually spun off to private equity, which, honestly, not much better.)

Monster’s problem, meanwhile, was perhaps that it boxed itself in. Jeff Taylor, the comapany’s founder, suggested in a podcast interview from earlier this year that he faced struggles with accelerating his business after the company went public. That caused it to lose a step as newer competitors emerged.

One example: The company apparently nearly had a job-sharing deal with LinkedIn, only for Taylor’s board to sink the agreement. While it tried to compete with LinkedIn by creating a professional social network of its own, that network eventually faded because it was secondary to the thing that brought in the bacon. (Big mistake.)

Meanwhile, newer models, like the job aggregator Indeed, started to eat Monster’s lunch—and the aggregators were allowed to siphon from the actual jobs sites like it was no big thing.

“The aggregator model was a fine model, but the Monster model was better,” Taylor said during an episode of The Chad & Cheese Podcast. “We actually had the direct line into thousands and thousands of daily jobs because we had direct relationship with the companies.”

This actually touches upon an important part of the early job sites’ models. Both Monster and CareerBuilder integrated themselves closely into the classifieds section of major newspapers, which in retrospect feels like both a savvy arrangement and an albatross, as it tied their businesses to the declining fortunes of the classifieds.

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In 2018, Monster tried going weird again, with a new monster, but it just wasn’t the same.

LinkedIn ate their lunch, no gimmicks in sight

In a way, I think the downfall of these companies is that they had to grow in tandem with legacy media, with Super Bowl ads and newspaper classifieds being excellent examples. That put newer competitors in a position to compete on a technical basis or even come up with new ideas that emphasized the culture of work rather than the process of getting a job.

Clutch soundtrack choice, LinkedIn—and not a monkey in sight.

It took LinkedIn all the way until 2016 to do a television commercial, by which point it was already well-embedded in many professional lives. Unlike Monster and CareerBuilder, there was no sense of whimsy to it—the ad screamed prestige. Within a few months, Microsoft paid $26 billion for the company.

That was a valuation neither CareerBuilder or Monster ever reached, though there was a time Monster perhaps could have gotten there. Instead, they were brought together last year by Apollo Global Management, a major private equity firm, with not much to show for it. (LinkedIn apparently once considered buying Monster, but it did not happen, with the firm spending nearly a decade as a subsidiary of Randstad instead.)

If you ask me, the reason these two legacy job board companies couldn’t keep it together was a mixture of poor branding and eroded user trust. Over time, both brands have been pigeonholed into one part of the career experience, which meant they weren’t useful when you weren’t looking for a job, and they weren’t top-of-mind when you were.

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Make weird corporate mascots acceptable again. (Phil Manker/Flickr)

On top of that, Monster in particular has dealt with a lot of data breaches over the years, which probably doesn’t help matters.

It turns out that people are more likely to look for jobs in places where they already talk about their job. Who would have thought?

All in all, I don’t think people really think about these job sites anymore. But if Trumpasaurus was still around, or if CareerBuilder had leaned more into the chimps, maybe they would have.

Stay weird. Don’t let private equity change you too much.

Job-Free Links

RIP Bobby Sherman, onetime teenage heartthrob and side player in the creation of The Sanchez formula.

I’ve been following the work of Burls Art, an oddball luthier, on YouTube for years. He started by making guitars out of colored pencils and has evolved from there. More recently, though, he’s recently gained an interest in metalworks—something he calls “inherently dangerous,” which I’m sure you’ll agree with in this clip that highlights some at-times-disastrous experiments.

Maybe Apple isn’t good at ads anymore. Or keynotes.

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Ernie Smith Your time was wasted by … Ernie Smith Ernie Smith is the editor of Tedium, and an active internet snarker. Between his many internet side projects, he finds time to hang out with his wife Cat, who's funnier than he is.