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Automating an email reminder to renew an annual membership

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Our neighborhood association (a nonprofit) has annual memberships that can be auto-renewed or just purchased year-by-year, via Squarespace - my question is mainly about the year-by-year membership.

We have a list we maintain that has a combo of memberships that have been purchased online, or purchased in person where a volunteer enters their information manually in the list (meaning that person does not have a Squarespace member account set up).

Either way, we have an expiration date in there, and we'd like to have an email sent automatically "x" days before their membership expires that takes them to the page where they can renew. My question is 2 part:

  1. For the people who have paid for their membership online, can we use Squarespace to send an email say, 7 days before it will expire, and direct them to the page where it can be renewed and if so, how? (If not through Squarespace, we do have a MailChimp account integrated w/SS but would need to know how to use MailChimp to do this).
  2. Assuming the first is possible, can we use the same method for people who were entered manually and do not have a SS account?

Thanks in advance for any help here! (I've been searching but not finding the answer to this specifically).

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1 hour ago, Qwerkin said:

For the people who have paid for their membership online, can we use Squarespace to send an email say, 7 days before it will expire, and direct them to the page where it can be renewed and if so, how?

If you've set the annual membership up as a "subscription product" in Squarespace, the subscription can be set to auto-renew annually. If subscription renewal notifications are enabled, Squarespace will automatically send each person a renewal notification email 15 days before their renewal date. The email explains the details of the renewal (price, renewal date, cadence at which the subscription renews) as well as a link to their account where they can log into their account and manage their subscription.

If you're using non-subscription products for the memberships, you'll need to set up a mailing list to notify them manually, using another service such as Mailchimp.

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