If you've got a special offer for your users, don't let it sit in their email inbox. Strike while the iron is hot by presenting the offer through in-app messaging.
When Josh Pigford of Baremetrics offered monthly users a free month if they upgraded to an annual plan, he originally did it via email. While he had some success with this approach, it wasn't until he switched to in-app messaging that he saw a 30% increase to annual plans. The reason for this appears to be context — the offer was presented while the user was working on the platform and (hopefully) deriving a lot of value from it. Compare that to email, where the recipient's receptivity to upsells at the time of opening is anyone's guess. And it's not just offers. Feature education, requests for feedback, etc. get increased interactions across the board.
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