From: Dropbox
Subject Line: Start using Dropbox!
Date: Thursday, February 10, 2011
While I appreciate a cute illustration as much as the next aspiringartist, and while I respect an automated message as much as the next digital marketer, I felt slightly violated when I received Dropbox's "Start using Dropbox!" email message. While I did download the software, I wasn't aware that I gave the company explicit permission to look inside my machine to see whether or not I'd actually installed it.
I believe they could have done right here by changing up the messaging. This message would have been better positioned as implicit rather than explicit. Less "we noticed you don't have the software installed," more "check out our installation tutorials!"
Tone is super-critical to data-informed automated messaging. Don't overlook the importance of your copy when it comes to these types of delicate messages.

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