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There is a company that really appeals to me, with two open positions that interest me. Both are very much programming jobs, that I would enjoy. I think I might like one than another but am not sure.

Is it bad, or seeming desperate to apply to both jobs? Should I apply to a specific one, but also mention that I think I could also be a good fit for the other? Or is it better to apply to both, and tailor a resume and cover letter for each specific job?

Are managers, in general, apt to think along the lines of "well, I don't think this is a good fit, but this job over here might be, let's make a time to interview you for that one."?

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    apply to both, and tell them that you did – Steven A. Lowe Sep 16 '13 at 2:32
  • Good company would automatically consider you for both positions. Apply for the one that appeals more to you. – CodeART Sep 16 '13 at 7:30
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Apply to the one you think you want, and also describe that you're interested in the other.

At many small companies there is actually only one job. They could hire two different positions, and whichever they get they'll shift other people around to cover the other one better than they had been. (And you'll get more hats than just the one if you want it.) In that situation having someone who wants both of those roles is pretty much perfect.

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    "At many small companies there is actually only one job." Yes yes yes. I have seen this quite a bit in small companies. – Monica Cellio Sep 16 '13 at 15:23
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There is no way to know how their hiring procedures work. Therefore try to apply for both and see what happens.

In some companies each applicant can apply to multiple positions but you can only have one resume and one cover letter in the system at a time. In other companies each job opening is a separate item so that you can have multiple tailored resumes in the system.

You have no idea if mentioning your interest in the other position will get your resume to the other manager in a timely manner. Keep in mind that with some small businesses the hiring software is just a standard email account. Others get most of their resumes from a recruiting company.

When hiring for generic positions, it is possible for recent qualified applications to be considered when additional generic positions are needed to be filled. If the descriptions and qualification are created from scratch each time, there may be no way of automatically be considered for other positions.

Some companies hiring procedures are so dysfunctional that they are hiring people with skill X at the same time they are laying off people with skill X because hiring managers didn't know about the about to lose coverage list, and the people on the list didn't know how to force their resume to the top of the pile.

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I'd say it depends on the mechanism you are using.

Automated Systems

I've seen a general style of automated system, many of them based of the same product - where you essentially build yourself an account and a profile, then submit your interest in certain jobs in the company's listing. It's not a size-of-company thing, it's just the interface - although I'd assume it costs enough that a very, very small company may not ever want to spend that kind of money...

In any system this abstract, I'd say it's worth it to apply for any job that interests you. The company will see your resume and note the interest in multiple jobs. Given that there's this system controlling it all, I doubt it will cause much chaos.

Personal Connections

If you ever go through personal connections, the first recommendation is to get the skinny from your connections. Job description writing is an abstract art form, and the insights from a friend can be invaluable. Do that first, and if you really are still interested in both options equally, go with your contact's guidance.

Writing to the Opportunity

If you're doing this in a more traditional formal, write a cover letter connecting the dots. Generally you can say in that letter why you like both options and what you want in a job overall, so that the person receiving your application can figure out what to do with you.

Behind the scenes

Generally, a company recruits by having someone inside or outside of the company take responsibility for finding candidates, screening them, introducing them to the process, and advocating for appointments with internal decision makers. To keep ownership clear, it's typical that the recruiter is responsible for some collection of open positions.

So - the big thing behind the scenes is whether both opportunities are staffed by one person or two. And if it's 2, how well they communicate. With one person, anything you can do to connect the interest in both positions is a good thing - like a cover letter. With two people, it's likely that your best interest is served by applying both places, and mentioning that you've done so whenever you get a call back on one of them. Hopefully the recruiters know each other well enough to keep each other in the loop, but that's not a given.

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