In search of some sort of marketing plugin

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I build funeral home websites. The sites get a ton of condolences which are just re-labeled comments. I am looking to automatically send emails to everyone who left a condolence on an obituary at the year anniversary of the date of death. Is there anything out there that would accomplish something like this? I do currently use Icegram Express to notify people that a new obituary was published but it doesn’t look like even the pro version of that will do what I want.

It does seem like creating my own plugin is possible but I would much rather find something that is already built if possible.

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