We talk a lot here about how the Employment System is broken. We talk about how Human Resources isn’t actually looking for resources, and how the “Apply” button on LinkedIn is usually a direct line to a digital trash can.
But sometimes, the absurdity of the process is so high, you just have to laugh so you don’t cry.
A reader wrote to me recently. He’s not a desperate job seeker — he’s a smart professional who got annoyed by the sheer incompetence of LinkedIn’s targeting algorithms. He decided to test the system by doing exactly what I always tell you to do: Do the job to get the job.
The result? A stark demonstration that LinkedIn usually doesn’t work. On the one hand LinkedIn claims its powerful AI matches the best candidate to a job. But on the other hand, LinkedIn clearly lacks the “intelligence” to avoid re-marketing the same job to a person the AI already rejected just a day earlier! How does LinkedIn square this disconnect with its claim that it finds people and jobs?
The embarrassing truth is this dog won’t hunt.
Here’s the reader’s story.
Question
I have been totally annoyed by repeated recruiter advertising on LinkedIn for a VP of Business Development role at Sesame Workshop. I am not qualified for this job. But the algorithm kept serving me the job and insisting I was the one.
So, I decided to apply. But I didn’t just send a resume. I used AI to generate a legitimate, high-level revenue growth strategy for them — basically doing the work of the VP before I even got the interview. I submitted it with a cover letter telling them to stop wasting money on LinkedIn ads targeting the wrong people.
My cover letter to Sesame Workshop’s recruiter started like this:
H-E-L-L-O! This cover letter is brought to you by the letters H, E, L, and O. Given how many times I have seen this ad… there is no doubt you have more than enough people in the applicant pool…
I don’t match the exact required experience, so why the heck are you paying LinkedIn to troll sub-optimal accounts?
What was the result? The Applicant Tracking System (ATS) immediately fired back an e-mail rejecting me and providing a link to apply to other jobs at the company. Clearly, no human ever saw what I submitted.
A couple of days later LinkedIn served the same job to me, encouraging me to apply. For jollies I tried again, but the employers’ algorithm “recognized” me and wouldn’t let me. Just how smart is it, I wondered? And how smart is LinkedIn’s AI? Does LinkedIn’s AI talk to Sesame Workshop’s AI? I altered my name slightly and resubmitted the same materials. This time it let me through. I got the same rejection e-mail the second time from Sesame via its jobscore.com ATS partner. Taken together, LinkedIn’s claims and behavior raise serious questions about its recruiting and marketing prowess.
Nick’s Reply
There are two main lessons here. The LinkedIn hiring funnel is actually a sewer pipe. And, this dog won’t hunt.
You provided a perfect case study of two massive failures in the modern job market: The LinkedIn Spam Machine and the ATS Firewall.
The LinkedIn spam machine
You asked, “Why the heck are you paying LinkedIn to troll sub-optimal accounts?”
The answer is simple: LinkedIn repeatedly spams you because HR departments (and LinkedIn!) measure activity, not results. That’s a critical failure point. The recruiter at Sesame Workshop likely has a metric to hit: “Generate 500 views.” They don’t care that the algorithm is succeeding or failing or spamming the wrong people again and again. They just want the clicks. You are a data point to justify their recruitment advertising budget.
The ATS firewall
I’ve never met a hiring manager that would ignore an applicant who offered a mini-business plan about how they’d do the job. I have preached for years that the best way to get a job is to demonstrate you can do the work. You did exactly that. You outlined a “YouTube-First Pivot” and a “Roblox Economy” strategy. You gave them free consulting. You gave them a roadmap to save their declining revenue.
In a sane world, a hiring manager would read that and say, “This guy might not have the years of experience, but he understands our pain points. Get him on the phone.”
We live in a recruiting world where rejecting a demonstrably good candidate is not counted as a failure of the AI. We live with an ATS firewall that blocks the candidate that shows they think “out of the box” — candidates like you.
The robot gatekeeper
You sent a thoughtful, strategic, and humorous proposal. But you fed it into a machine that only understands binary code and keyword matching.
The ATS scanned your resume. It didn’t find “15 years of Muppet Management.” The robot doesn’t know what “strategy” is. It doesn’t know what “humor” is. It definitely doesn’t know that C is for Cookie and S is for Strategy. It scored you a zero.
So, it sent you the standard “Dear Candidate, please go away” e-mail. Twice.
The Takeaway
If you had sent that same 5-point plan via FedEx directly to the CEO of Sesame Workshop, or if you had found a board member and e-mailed it to them directly, you might have a consulting gig right now — or at least a real shot at it.
But the moment you clicked “Apply” on an automated system, you ceased to be a consultant offering value. You became a row in a database.
The lesson for everyone else: Stop feeding the LinkedIn robots. They have no appetite for your value, your humor, or your solutions. (Some critics go farther and say Job boards like LinkedIn are dead.) Stop waiting for LinkedIn and the HR department to come find you. Because that dog won’t hunt.
LinkedIn: Does this dog hunt? Is it really the leading source of jobs and hires? Does it find the best people and fill the most jobs? How effective is it for job hunters? Is it a job board or a marketing engine that sells little but promises while delivering the bare minimum? What’s LinkedIn to you? Have you ever “done the job to win the job” to impress a hiring manager only to be ignored by a robot?
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You’re asking a very good question for which I think there is no answer anyone wants to hear! Over the long term there are really no “safe” companies or jobs, especially in this economy. A stockbroker (“financial consultant”) friend of mine explains it like this:

HOLIDAY
I have a simple rule when job hunting, no matter where in the process you are. You goal is to never walk away empty-handed. If you don’t get the job, your goal is to get at least one other name from the employer you’re talking with: a referral to another manager, another chance at a job.


Making good hiring decisions may not be as challenging as doing Physics, but it is just as easy to make a serious hiring mistake as it is to err in a complex mathematical calculation.
Yes, it really happens. I’m not a lawyer but trying to sabotage a job offer may constitute 
“Okay, I’ve told you what I make. Now in return please tell me what the salary range on the job is before we start this interview, so we make sure we’re both on the same page.”
You know you have a problem when an interview isn’t about the work. Instead, you and the manager are talking too much about peripheral things and very broad topics. Or, your skills are being discussed only in very general terms, instead of how they will specifically apply to the job at hand.
Do you still use the job boards to look for a job, or to recruit if you’re an employer?