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If customizing a resume is likely to work at a company, according to the conditional probabilities I have estimated, working there will make me less happy than working at a company that does not exclusively prefer specialists. Since it also involves an additional investment of time, that means the posting itself would have to be closer to my ideal vision for a job working for The Man.

Companies use barely-functional pattern matching algorithms to automatically toss your resume into the garbage. It is very likely that any effort you spend hand-tailoring your self-advertisement will be wasted anyway. But let's assume that you're doing it to pass the bozo filter and talk to a real person.

If you have to feign specialization to get past the auto-rejector, it is safe to assume that the company sees fewer qualified candidates. Supply is lower. As long as the posting remains open, demand remains the same. Therefore, the more specialized the role, the higher your expected remuneration should be. It's fine that companies are picky, but not both picky and cheap.

My advice is to use a general, unmodified resume for all your initial applications, and only to tailor your resume if the company does not respond in person after the first 2 weeks. If that generates a response, remember to ask for a higher salary if you reach the negotiation phase.

Of course this, like most other advice, should be taken with skepticism, because it is based on my experiences, not yours.

Honestly, I don't spend much time customizing a resume, because I already have a job, even if I don't like it, and a lot of the postings that I see are just as flavorless and uninspired as an untailored resume. My primary criteria for applying are whether the job itself seems like it could be interesting after you subtract the HR boilerplate and whether the company makes it easy for people to submit themselves for consideration.

If applying is as easy as writing an e-mail with a resume attachment, I will take the time to write an original cover letter. If I have to jump through 8 pages of hoops where I have to re-enter my entire resume into a series of tiny text boxes, I will not customize anything. And on the 8th page, where I am asked to list 3 of my weaknesses in an HTML form, just above a request for my entire salary history, I will almost invariably list "I get snarky when confronted by foolish or wasteful hiring practices." At that point, I have already invested that much time on an application that I know will not yield fruit, so I can't help but feel bitter about the utter waste of it.



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