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I did similar things when I was on the job hunt. I wrote one cover letter per company, as the positions I applied for were very similar. I'm guessing you're not applying at this place for a position in the accounting department and a position in the PR department, right? I work in marketing so all the positions I applied for were very similar and I tailored my cover letter to speak to the job type more than the specific role.
@Mrs. Fireworks: So you don't think it reflects badly to send out a cover letter to more than one position, right? They're definitely all pretty similar (social worker/counselor for children's program, and then program director for children's program, for example).
I'm currently doing the same thing. I am applying for very similar roles for the multiple positions within the company so the same cover letter with just the position title changed has been working just fine for me.
@hilsy85: Yeah definitely send out a cover letter for each position, but change it slightly for the job position title. Your skills will be applicable for each position, so the bulk of the cover letter won't change much, just the specific sentence or two surrounding the actual job role. The more you apply, the better chance you have of being seen by HR, so go for it!
Good luck!
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So I'm currently job hunting...some of the agencies that I've been looking at have multiple openings that I would be interested in/qualified for. What's the right way to go about writing separate cover letters for different positions within the same agency? I feel kind of funny writing a cover letter stating why I'd be such a good fit for one position, and then writing another cover letter stating why I'm so interested in a different position. Thoughts?