Howdy! Despite being in SEO for a few years, I don't have the slightest idea when it comes to email marketing. A good friend of mine is applying for his internship and I am helping him to blast emails of his internship application to a total list of 500 companies. There will be two attached file (Microsoft Words format) when sending out. So, here's the question. How do I send his resume out to a total list of 500 emails? What tool do you recommend? I understand normal email providers (Gmail, Hotmail, etc) can do the job but how do I send out in a way that the emails are sent individually and not copy paste the entire thing into recipient (that would look like spam) to each email address without having to do the same steps more than 500 times? Note: 1. Email blast to 500 email addresses 2. Two attached file (Microsoft Words) 3. No rush (Can be spread over 1-2 or more days) 4. Do not mind to pay the extra fee 5. Does not get banned or flagged (Email will land right away in inbox instead of Junk) 6. One click and leave it there P/S: To those who tries to sell his email marketing service, no thanks!