Very interesting concept! I was about to dive right in when a voice in my head reminded me that my inbox discipline is terrible and I don’t need even more automated emails that will serve only to increase my unread count (which currently stands at 16878 in my Personal inbox).

Have you considered expanding this to notify via other mediums such as iMessage (if possible, this would be my preference) or the presumably easier WhatsApp/Telegram (the Telegram Bot API is pretty great, I’d imagine would be very easy)?

I’d also echo the free trial sentiment expressed elsewhere in the comments, take the mythical drug dealer approach and get ‘em hooked on freebies!