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Does it look bad to apply to multiple positions at the same company?

It’s very common and normal to apply for multiple positions for the same company. More than likely there will be a different HR person every time. Different HR rep, different department, different hiring managers, different interview experience, even different location. It’s perfectly normal so go for it.

What positions should be on a resume?

For many people, the Job Title on their resume is the same Job Title from their last job. If your last position was Director of Software Development, then this is most likely the Job Title you want to use. But, if you are seeking a new position, then you should use that Job Title on your resume.

How many positions should you list on a resume?

Start with the most relevant experience Include only those of your jobs that are relevant to the opening. If you aren’t a recent graduate or senior executive baby boomer, you’ll probably include no more than five positions that span a total of no more than 10-15 years.