Email workflow

Outlook version
Outlook 2010 64 bit
Email Account
Exchange Server
#1
Is there a way in Outlook to set up workflows? Our insurance agency sends emails to policyholders if they are being cancelled for non-payment. The canned email .oft templates include the cancel date. After the first friendly email we then send a 2nd request and finally a policy lapsed letter. I'm trying to see if there is a way for Outlook to generate the 2nd request and lapse letter automatically based on the cancel date.
 
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
#2
You could use VBA to do it. SharePoint workflows might also work but VBA would be fairly simple if you are using templates. You could prepare all 3 letters at ones with deferred deliverly on the other two or use reminders to trigger the additional letters - see http://www.slipstick.com/developer/send-email-outlook-reminders-fires/ for one example.

My only concern would be removing the additional messages once the bill is paid. Depending on how you track payments and cancellations, you may be able to do a mail merge to create the messages daily or weekly.
 

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