A good job listing tells you a lot about the role. A bad one tells you a lot about the company behind it. And these two job listings posted recently by Outside tell you everything that’s gone wrong with the company’s approach to content over the past two years.
Past is Prologue
Not to be conflated with Outside, the long-running magazine it purchased in 2021, Outside Interactive, Inc., is a venture-funded conglomeration of loosely-related tech and media brands that’s recently devoured broad swathes of the cycling news ecosystem.
Signs the company may have bitten off more than it could chew began arriving last November, when Outside CEO Robin Thurston euphemistically asked middle management to “reimagine” their teams for the second time in six months.
[Pausing here to explicitly call out that I’ve worked repeatedly with CyclingTips, and other Outside brands, both before and after their Outside acquisition.]
At least four cycling editors were let go as part of those layoffs, three of them from road cycling publication CyclingTips. That, combined with the resignation of CyclingTips founder Wade Wallace back in August, led to pretty much everyone else leaving that title as well.
Rumors swirl around additional motivations, but suffice to say, the departures were widely-noted and provided rich fodder for gallows humor. That Outside needs to bring in a few bodies to shore up its cycling coverage should not be surprising.
Is There An Editor In The House?
What should be surprising is that these job listings are a shambolic pile of flaming hot garbage. Outside is, lest we forget, funded to the tune of $174MM. Their investors include Sequoia Heritage, a spin-off of VC heavyweight Sequoia, and reasonably successful in its own right. You’d think with such backing, the basic task of laying out job openings in text would be doable. Apparently not.
It’s easy to joke about poorly-edited copy being the result of laying off all your editors. And don’t get me wrong—the sloppiness and typos you’d expect are most definitely there:
Hey Job Candidates—U Up?
But this isn’t about quaint nuances of composition or professional fine-tuning. These listings are just fucking bad, and bad in a very obvious way. If you were drunkenly making up jobs for your ex through a series of texts on an iPhone keyboard at 2am, they would come out looking something like this.
They’re bad enough that I don’t think anyone bothered to so much as scan them before they were published. Read the following sentence aloud to someone with even a rudimentary grasp of English and they’ll tell you what I mean:
Within 6 months, you will:
- In the first six months the Senior Tech Editor will plan, create, and orchestrates all gear coverage for the Outside cycling group including Outside Cycling Group, CyclingTips, VeloNews and Outside, and works to provide consistent, relevant, and exciting gear content on all platforms.
While you might expect an obvious flub like “the Outside cycling group including Outside Cycling Group” to be a one-off, similar errors are everywhere. “Within 12 months you will:” introduces a set of grammatically and logically un-attachable bullet points like “Excellent written and verbal communication” and “Understanding of modern bicycle technology and application”.
Pass The Copypasta
What’s really interesting is how many of these errors appear in both listings, so I ran them through diff. They aren’t just similar—they are the same. The handful of changes are cosmetic, mostly just swapping out the word “Senior” and attempting to differentiate a “lead” role from an “assist” role. Even then, the work is sloppy—line 19 below leaves “lead and manage” in for both titles.
On some level, I get this. Overlap between these two roles is going to exist. It would be bad practice to not economize the crafting of one listing by reusing parts of the other. But Outside takes that to an extreme, changing only 2% of the words between roles. It begs the question: if these jobs are only 2% different, why is there (potentially) a 90+% divergence in salary?
It also makes me curious why Outside—ostensibly a content-focused company—took such a different approach on these Senior and non-senior Python Engineer positions posted last winter. When fed into a diff tool, their only meaningful overlap is legal boilerplate, while the salary ranges are substantially closer.
A Content Position Where Words Have No Meaning
The archived Python Engineer listings also hammer home the concept of a “Senior” title— “10+ years experience” and a laundry list of development platforms, versus just work “creating scalable API’s using Python”. But in the Bicycle Tech Editor roles, the difference seems limited to the “plus” after “4 years of experience”.
Let’s compare the Outside listing (it is just one, really) to a comparable Senior Editor role at Glamour, under the umbrella of content monolith CondeNast:
Note how much more clear and specific this listing is than Outside’s. Candidates “top edit”, “grow freelancer networks”, and “develop ideas” based on analytics. Outside leans on the the broadly ambiguous “create” and “orchestrate”. The products Glamour’s role delivers— “compelling headlines”, “essays our readers can’t find anywhere else” —are similarly detailed compared to Outside. Note also that the Conde role is specific to the Glamour masthead, with nary a typo in sight.
More informative still are the job requirements: “proven track record of original reporting”, “strong roster of professional contacts”, “able to toggle between first-person voice and objective tone”. By comparison, Outside mentions “working on bicycles” more times than it calls out anything specific to writing. And those of you pointing at “Excellent written and verbal communication”, take a seat at the kids’ table. You’ve just excused yourself from the burden of a valid opinion.
It’s Hard To Ask For What You Don’t Know You Need
Taken as a whole—and disregarding the typos—this listing is bad because its authors don’t have any actual idea what they need. It’s a laundry list of wants people that don’t understand content associate with content creation.
For example, there are asks for still photography skills—with the paradoxically prescriptive yet non-specific condition of a “DSLR or similar-level camera”. There is a call for “Deep understanding of video content creation”, which could be anything from making TikToks to correctly setting finish line camera height. And of course there’s casual mention of social media and WordPress, with (again, unlike the Glamour listing) no clarity in how the role will need to use those tools.
Part of why this feels so confused is that it’s not for any particular publication or platform, but the “Outside Cycling Group”. It’s extremely hard to define what makes content “consistent” or “relevant” without knowing what masthead—or even what format—it’s going to appear in.
Taken with the lack of specific skills, it seems inevitable that whoever gets hired for this role will make generic, likely advertiser-driven content, with whatever brand is convenient slapped on after the fact. Indeed, the cross-posting has already begun.
As CyclingTips founder Wallace noted in a subscriber newsletter last year, “Our biggest worry with any type of content syndication is that [VeloNews] and [CyclingTips] will end up looking identical and being a watered down version of both. Nobody wants this.” From these job listings, it would appear that Outside management disagrees.
If Content Is King, This Is Regicide
If you’ve read this far and think “Cosmo—you’re looking way too hard at a couple of botched job postings”, I get that. These went live right before the holidays, probably on very short timelines given the accelerated CyclingTips exodus. There is certainly a universe where a sound, competently run, content-aware business might have stumbled into putting these out.
But that universe is not ours. These job listings are the best examples yet of how the current management of Outside Interactive fundamentally does not understand content.
Let’s recap with dots:
- These are job listings for content creators
- The content in these job listings is full of obvious errors
- The method used to create the content in these job listings is transparent, cynical, and substandard
- The job listings betray a lack of internal awareness around content creation roles
- The qualifications in these listings don’t have much to do with generating content
- The type of content these jobs are going to create is extremely unclear
- The content these roles will generate has no well-defined platform, audience, or objective
- The job listings suggest Outside doesn’t understand the connection between content and brand equity
At the “high-paced content organization” these listings purport Outside to be, basic competence would have stopped the presses on this weeks ago. At the very least, these openings would have warranted fire-drill fixes the moment they went live.
Instead, senior Outside executives broadcasted them to their professional networks. The fact that—at time of writing—they’re still posted in their original, dumpster-fire state is impressive. Factor in the ongoing and active LinkedIn trolling from former Outside employees, and it’s truly astounding.
The Knowledge Is Fifteen Feet Under Their Asses
It’s important to note that my beef here is with leadership. Even after the departures, Outside’s brands are strong in creator talent. As uncomfortable as I might be with the occasional Barstool vibes, PinkBike is always dialed, from Friday Fails to the World Cup.
Outside’s title publication still isn’t afraid to take on potentially sponsor-unfriendly topics. And every person I’ve worked with at CyclingTips has been awesome. That the parent company would blindside the remaining talent with these job listings is simply mind-boggling.
Ultimately, Outside leadership needs to realize that good content doesn’t just “happen”. It’s not audience demographics, company objectives, and corporate buzzwords standing on each other’s shoulders inside a trench coat. And it doesn’t sprout spontaneously from fresh piles of business-plan horseshit—not even when the job listings have the perfect set of typo-free bullets.
The best content—the kind that attracts large audiences, that people want to pay for—is made by talented, passionate creators. They have specific, hard skills, and work best with consistent platforms and clear objectives. Things like what they’re making and who they’re making it for.
At the end of the day, Outside’s brands are only worth what their audiences will pay—be that through eyeballs or memberships. Those audiences are engaged primarily through content, and that content is only as good as its creators.
If Outside leadership truly sees content as a “core pillar” of its business moving forward, they need find out how it works from the people who made their brands worth acquiring in the first place—preferably before laying any more of them off.