Question, from a 2010 grad: I’ve been browsing position openings, and I found two entry-level positions at the same company that are a strong fit for where my skills are and what I want to do. Both positions are in fundraising, one concentrating more on individual giving and the other on foundation/corporate relations. I’ve heard that applying for two positions in the same company makes you look unsure of what you want to do, but I see both opportunities as areas to grow in. Would it be a faux pas to apply for both positions? If not, do I send in a resume and cover letter for each position or do I address my interest in each in the cover letter?

Answer: Great question! I don’t think there’s a clear right or wrong in this situation. I consulted a university alumni career counselor friend on this one. Here’s what she suggested: For one, it’s helpful to know more about the organization. If it’s a large institution like a university with many departments, you can’t assume the openings are in the same department. Different departments have different hiring managers. Best to apply for both separately. As a recent grad, you have less to worry about appearing unsure of your interests. It’s expected that you’re figuring that out and looking to grow. Generally, there’s no harm in doing two applications. If they land on the desk of the same person, they will see you took the trouble to customize two separate cover letters.

Better still, you can use your personal network to find someone who knows someone at the company (this is why I love Linked In) and ask what is the best way to be considered for both positions. Even if you do not have a personal contact, try to find out who the hiring manager is for each position and address your cover letter to him or her.

If you are applying cold with no referral through your network, my university contact recommends using nice paper, a nice envelope, and putting the application in the US mail as a way of standing out. I’m a big fan of networking but when that’s not yielding any results sending an application in the mail in addition to any online instructions could be an interesting experiment.

Good luck! Anyone else face this situation and have suggestions for our jobseeker?