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PS: Any recommendations on a good service for this? Looking at AWeber, MailerMailer, and FollowUpMarketer....
As far as I'm aware, personal data such as email addresses can only be used for the purpose for which it was collected (in the UK, anyway). So if your customer gave you an email address as part of a checkout/payment procedure, you may only be able to use it in relation to that procedure.
There may be some leeway if your follow-up is explicitly related to the purchase though, as your post suggests. I'd be concerned at receiving 3-5 follow-ups though.
One thing I have seen is where a potential customer has entered personal data (including email address) as part of a checkout procedure, but then failed to complete payment. I know one major UK site that will then send the 'customer' an email along the lines of 'we notice that you registered with us but did not purchase. If there was a problem with our checkout procedure we would be pleased to assist you in any way. You can also telephone your order on ... etc' (you get the idea). Personally I don't think this is spam, and apparently this method converts about 25% of their abandoned cart users.
There is some idiot company - Nature's Way or something - I bought one thing from 2 years ago. Despite following checking the "no email offers box when I ordered, and following the desubscribe instructs numerous time, and writing letters to their customer service dept, I keep getting their spam. Guess who I will never buy from again, and badmouth every opportunity I get, on any public forum?
likewise, what quiet_man said about contacting "nearly" customers to check if there were any problems is fine - again, stick to that, don't make it a sales pitch.
all sales pitches should be in a separate opt-in mailing list. you should give customers the option to opt in (they must opt in, not opt out) and tell them what they are opting into (newsletter, special offers lists etc), how frequently you'll email them (monthly, weekly, 10 times a day or whatever), and what you'll do with their email address etc (ie, will you only use it for your own service or will you pass their personal information on to other companies?) and so on.
I guess I will just keep it at 1-2 max - 1 week after shipment - and then one month - we have a 30 day money back guarantee...
... Or just 1 at 2 weeks after purchase.
Then hit them with a direct mail postcards after that.
And yes - the new Store and Shopping Cart will have an opt-in for the Newsletter and Catalog.