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I'm looking to create a couple mailing lists for customers, but I'm not sure the best way to go about it or best service to use. I'd be gathering mailing subscribers through a WordPress website, if that matters.

I was thinking of using a mail list service like Mailchimp or Convertkit but I'm not sure they'll have all the functionality that I'll need.

I need:

  1. the ability to create multiple lists - free and paying subscribers
  2. a way to charge the paying subscribers monthly automatically once they're on the paid list
  3. the ability to send different types of content based on the subscriber level - aka one will get full articles when they're published on the site, the other will only get excerpts

This might also be achieved by some combination of site membership/mailing lists.

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MailChimp/Campaign Monitor all allow for multiple lists...

Two problems it seems:

  1. Charging visitors before they are added to a mailing list service

You can use something like GravityForms (PayPal) as the Pay Wall to the premium list. GF also has MailChimp/CampaignMonitor connectors, so from memory you can conditionally tell GravityForms to only process your chosen mailing list connector after a successful paypal transaction. You should be able to send subscribers to either the paid or free lists

EDIT: In PayPal your product would be recurring. Not sure how you would remove a subscriber once they've cancelled their recurring PayPal?

  1. Different types of content

Campaign Monitor (CM) allows automation, so you can feed your Blog's RSS into a CM workflow so that it will automatically send an email every 4 weeks with new content from your blog. If there is no new content then it won't go.

How you format that content in CM is down to you and the email template you are using, whether you show the excerpt or full article

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