What's the best mass email / drip email solution?

I use Google Apps for Work. Each of my contacts is an organization and each organization as 3 or more email addresses. I want to send an email to each organization (preferably using a mail merge option). What I want to do is to list all the emails associated with the contact in the To: field so that each recipient can see I have sent this email to all of the top 3. So if I have 45 contacts with 3 emails each, that would be 135 individual email addresses. Rather than sending 135 emails (using the email merge option) I want to only send emails to each organization, which would be 45 emails. Further more I have a series of 9 emails I'd like to send them. When they reply to the first one, I'd like the 2nd one to go out at the next scheduled sequence. If they don't reply, I'd like a follow-up email to be sent. This would continue through the whole sequence of emails. Anyone have any thoughts on how to make this happen? Thanks!
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