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Square Marketing is always excluding people from newsletters. Why?

I am trying to use Square Marketing newsletters to update frequent customers, and also for periodic employee newsletters. Our Customer list mainly consists of people who have transacted business with us over the years, and I've also manually added Customers.

 

For whatever reason, it seems I can't send a newsletter to anyone who's "Last Visit" was "Never" as per the Customer screen. Why is this? What is the workaround for this?

 

Example 1: I want to use Square Marketing to send automated newsletters to our employees. I added our employees as Customers. When I add them to a group called "Employees", I go to select the Employees group for the newsletter and despite it having people in it, the audience size is "0" for the newsletter. 

 

Example 2: We have Customers who have transacted business with us over the years. These Customers show various Last Visited dates. There are other key people who work at these Customers who I'd like to inform of updates. I manually add them, and they are excluded from the Marketing newsletter audience.

 

Why can't I email people who I've manually added?

 

I've even shared Square profile link updates and had them manually update their profiles to receive newsletters, but it will not work.

 

We have 600+ email subscribers at another major mail list provider. I see Square has an Import feature. But if I import all of these people, they'd have no Last Visited history and thus I would assume they won't be eligible to receive newsletters. I've called Square Marketing support twice and spent almost 2 hours on the phone and nobody could give me a clear answer on this.

 

Can someone confirm if a Customer MUST actually do a transaction with you to be eligible for a newsletter? This seems like a ridiculous, **bleep** poor implementation of the newsletter system if that is the case. 

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