With the exception of their email templates (which aren’t the most inspiring), everything about Constant Contact is generally quite good. Unlike other email marketing tools, there are no bells or whistles with Constant Contact. You’re probably not going to be blown away by any of their features, but equally, there’s nothing too underwhelming either.
A. Yes, and the FTC has issued a rule under the CAN-SPAM Act that governs these messages. Messages with sexually oriented material must include the warning “SEXUALLY-EXPLICIT:” at the beginning of the subject line. In addition, the rule requires the electronic equivalent of a “brown paper wrapper” in the body of the message. When a recipient opens the message, the only things that may be viewable on the recipient’s screen are:
The primary purpose of a transactional email is to convey information regarding the action that triggered it. But, due to their high open rates (51.3% compared to 36.6% for email newsletters), transactional emails are an opportunity to introduce or extend the email relationship with customers or subscribers; to anticipate and answer questions; or to cross-sell or up-sell products or services.[4]

When you send out spam, you can flip that number and you'll see less than 20% actually make it in, if that. So we recommend getting permission. Create a Signup Form and put it on your site. Sign up customers for your emails when they make a purchase. Whatever you do, make sure you have permission so that your email marketing campaigns aren't sent in vain.
A. Whether a seller or forwarder is a “sender” or “initiator” depends on the facts. So deciding if the CAN-SPAM Act applies to a commercial “forward-to-a-friend” message often depends on whether the seller has offered to pay the forwarder or give the forwarder some other benefit. For example, if the seller offers money, coupons, discounts, awards, additional entries in a sweepstakes, or the like in exchange for forwarding a message, the seller may be responsible for compliance. Or if a seller pays or give a benefit to someone in exchange for generating traffic to a website or for any form of referral, the seller is likely to have compliance obligations under the CAN-SPAM Act.

Thanks Kelly, Mailchimp have definitely come a long way with their UI over the years, it’s just their service that hasn’t caught up ;) I haven’t had the chance to play around with Pure360 as much as I’d like, but I’ve heard the same things echoed by several friends who use their service. Looking at their client list, I think they’re more aimed at large companies though. 
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