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Variants of this question have been asked before, but I could not find an exact duplicate for this situation:

Some company offers jobs A and B. The jobs are very similar, and I wish to apply to both, but I cannot do it simultaneously, their processes force me to apply separately for each job.

Now, I have written a cover letter for job A. Which of the below approaches should I now take:

  1. Rewrite the cover letter so that it mentions both jobs A and B and applies more generally to both jobs (this is doable since the jobs are similar). Then apply for jobs A and B separately but attach the same rewritten cover letter to both applications.

  2. Keep the cover letter for A, and write a slightly different cover letter for job B, which focuses more specifically on the responsibilities required for job B. Then apply for both jobs separately, using their separate cover letters.

I am unsure what to do.

Normally, I guess you'd go with option 2 since it seems more genuine and shows a separate interest in either job, but I feel it has two drawbacks that option 1 does not have:

  • Firstly, option 1 makes it clear that I am one single individual applying to both jobs. Option 2 does not indicate this at all. This might lead to some confusion if my two separate applications are read by 2 different managers, and they both offer me a job.
  • Secondly, if I go with option 1, then the company only has to read my cover letter once. If I go with option 2, I'd be sending in two almost identical cover-letters, that differ only by a few sentences. So if, for example, the two applications are read by the same manager, that manager will be reading my cover letter twice, one of them only slightly different than the other. That doesn't seem very ... optimal, does it?
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  • Why is this question getting down voted? It's a perfectly reasonable one. – Skater-Boi May 1 at 13:14
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    Similar how? Similar, like they're on the same team, or similar as in they're the same role for two different job functions? – user70848 May 17 at 18:25
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Write two cover letters. Each tailored specifically for one job. Any cover letter should be tailored to the specific job you are applying for otherwise you would just have a resume or CV.

You have no idea how their hiring process works, and it's possible that your cover letters will be sent to two different managers who are each looking to fill one of the positions. Do you think they want to read half a cover letter on why you would be great at another job in the company?

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Be transparent.

The job of your cover letters is to get you an interview, so write a cover letter for each job explaining how you are great for that specific job.

And, mention the other job in each cover letter. Something like,

"I also applied for Acme's Senior Widgeteer position; I have the qualifications and experience to fill that position as well as your Principal Widget Wrangler position. Working at Acme is an excellent opportunity for me."

This way you help them avoid confusion, and you reinforce your interest in the company.

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