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When a job application asks me to enter job info, after uploading a resume, should I re-enter all the positions on my resume (jobs/clubs/etc.) or just the relevant ones or just paid jobs? I am a college student by the way.

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Generally it's wise to put in all the information that is relevant (or ones that you wish the company to consider).

When it comes to unpaid jobs, there usually is a section for community service or volunteer work where you can include that kind of information.

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Yes. At least this shows you're willing to put in the effort. I would also wager that this helps them as CVs cannot always be split into information.

Unless your skillset is so in demand that they are the one asking you to please apply, you should partake.

Though I would advise to only provide elements that ar only of use or help you stand out in a good way.

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