I found two jobs that I want to apply for from the same employer. One is a software engineer position and the other is a “data specialist”. On each listing requests an email with a resume and a cover letter.
Since I want to apply for both, should I send one email and mention both positions in the subject and body? One cover letter or two? If it matters, both jobs are fairly similar to each other. They’re both on the information/technology spectrum.
That’s a tough question. A lot of applications are first reviewed automatically. So “Re: Engineering Position”, may get forwarded to one person, and “Re: Data Specialist” may get forwarded to someone else. But if one single person gets both, there may be confusion.
Hmm… email them separately, but then add an explanation in the body of the emails? 
Whenever that’s happened to me, I check out their instructions. If the email contact is the same and they don’t spell out “one email per position please”, I send a single email, mentioning both position’s codes in the Subject and explaining that I’m interested in both in the cover letter.
As in your case, it’s always been positions which were very similar. I’ve gotten hired that way twice (they’re always contract positions, so don’t take my “needing to look for work again” as bad news, it’s just business as usual in the freelance world).
I’d do separate ones because in this situation I’d want to write two different cover letters each explaining why I’d be best for that job.
Where I work you’d need to send in two different applications for the very same job in two different locations because there’s a silly application with a vacancy number and all that.
Depends on the company. Some are OK, or even encourage changing positions within the company, and those would most likely have no issues with considering you for multiple positions. Others have managers that run their own little fiefdoms and would see such behavior as blatant disloyalty, or at best trying to cheat the system. I haven’t followed them much, but back in the late 80’s TI was very much the former.
When I was graduating from college, I had interviews for three different positions at TI. (obviously a very different job market for EE’s then than now!) All of them were aware of the others, and the HR people were quite happy to be supplying a candidate for three positions with only the expense of one interview trip.
I ended up with offers for all three…but Dallas heat? no thanks! I ended up taking a job in a nicer climate where I would eventually be reprimanded for looking into changing departments. “hallway recruiting” were among the words used.
I would send different emails but mention (in a positive light) that you are applying for the other position (as you are deeply interested in their company or some such stuff).
So if I’m sending two cover letters, is it okay if they are very similar but tailored in some parts for the specific positions? And some parts of the letter are identical?