Front's Trial Reactivation Email

Expired trialing users are a goldmine of opportunity if excavated correctly. Front is a prime example of how to reach out to old trial users who didn't convert into customers without spamming or annoying them. Note: this email has been reproduced for formatting purposes.

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It's rare you see an opening to an automated/mass email that still reads like a personal 1:1 email. That's because it isn't cloaked in business jargon that makes it a marketing #deadgiveaway. It also cuts straight to the context of the email: you started a trial and didn't become a customer. But the tone makes it disarming, instead of alarming.
This small touch tells the receiver that it's okay that they didn't convert from the trial, essentially providing a reason for the receiver to justify their actions. It further disarms the receiver. Guilt-tripping rarely works. Empathy always works.
Instead of asking a question (notice that there isn't a single question mark in the email!), Mathilde simply puts an offer on the able, so to speak, for anyone interested in revisiting Front. The call to action ("re-open your trial for 7 days") is still bolded, but it doesn't dominate the email as a whole.
She also offers to connect the receiver with a "workflow specialist" for a "free training." If you read between the lines enough, you'll understand that it's really a demo with a salesperson. But honestly, who cares? A workflow specialist sounds much friendlier than an Enterprise Account Manager. A free training is much more appealing than a demo. Is it semantics? Maybe. I think it's genius framing.
No hopping on a call. No synergies. No baiting questions. Just a signoff that lets the receiver know the offer is there while still implying that a reply is expected.
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