Should you tailor your resume for every job?
For any job you actually want, yes.
A generic resume asks the reader to work out for themselves why you fit. Most readers do not take that job on. They give it a few seconds, fail to find the thing they were looking for, and move to the next one. The tailored version does that work for them by putting the relevant thing first.
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What tailoring is not is rewriting your career per application. It is mostly selection and language: choosing which of your real achievements to lead with for this specific role, and describing them in the vocabulary this employer actually uses. Your work does not change. Which parts of it are visible does.
The reason people skip it is arithmetic. Done by hand, tailoring runs 30 to 45 minutes per application, so by the fourth job of the evening it quietly stops happening. That is the part JobShifu compresses, and it is the only part worth compressing. If you would rather run the loop yourself, tailoring a resume with a free AI chat walks through it step by step, including the checks a chat window will not do for you.