Hi @JimT95!
Constant Contact Service Provider AND Boston Real Estate Broker here! Congrats on all the listings!
I completely understand what you are trying to accomplish but you may need a work around for this because this would be more of an advanced feature that a CRM would have.
What you could do is use the birthday field for one of the client's expiration dates and use the anniversary field for that same client's other listing expiration date. Then schedule the birthday club and anniversary club emails to send emails to them in advance.
Another recommendation would be if you use Dotloop, create a task inside each of the listing loops with the expiration date to follow up with your client. Dotloop automatically will email you when you have a task due. You could have 1 task be a 14 day reminder, 30 day reminder, etc. This is what I would do personally and just have an email ready to go and saved as an email signature that you can reuse.
Alternatively, you could use a recurring email reminder set up like Boomerang, which may be a better fit in this situation, if you use Google for email.
I hope this helps!
Lindsay
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