how to apply for multiple jobs at one company

A reader writes:
There is a community development organization I really want to work for because it seems to fit my personality very well; they share an appreciation for community outreach, planning policy, and youth. However, I am interested in two job openings. The first position is within the field of my professional degree, but I might be under qualified with my years of experience. The second position is working with youth, which I have volunteer experience in but might [face] grueling competition in this economy. Is there a way to apply for both? Or do I have to choose? If I must choose, which one would you suggest?

You can apply for both, but you need to be careful about how you do it.

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