By Tom Carter · AlexDLY · Updated June 2026 · 4 min read
Trials that expire without upgrading are the cheapest revenue you are ignoring. They already know your product. This agentic workflow re-engages them with proof and a reason to come back, while you sleep.
The workflow
Trigger
trial expired, no upgrade
›
Enrich
usage + firmographics
›
Score
likelihood to convert
›
Draft
win-back in your voice
›
You approve
one click
›
Send + book
email / DM
How it runs
A daily trigger finds trials that lapsed without converting. The agent enriches each one with how much they actually used the product and who they are, scores their likelihood to come back, and drafts a personalized win-back referencing what they did in the trial. You approve in one click. The agent sends and books the call. Nothing risky goes out without your nod.
The copy to steal
Three message variants the agent drafts from. Copy any of them and tune to your product.
Email · win-back
Subject: the one thing you didn't get to try
Hi {first_name}, you set up {product} a few weeks back and ran {usage_signal}, then it went quiet. No pitch here. Most teams stall at the same step, and there's a 5-minute setup that usually unlocks the result you came for. Want me to send it, or grab 15 minutes and I'll walk you through it on your own data?
LinkedIn DM · soft re-open
Hi {first_name}, saw you trialed {product}. Curious what made you pause. If it was {likely_objection}, we changed that. If it was timing, no worries. Either way I'd value 60 seconds of honest feedback.
Follow-up nudge · day 4
{first_name}, last note from me. Here's a 2-minute clip of the exact workflow other {industry} teams use to get {outcome}. If it's useful, the door's open. If not, I'll close your file and stop the emails.
Delegate this workflow
Recommended owner: an AI agent — it runs autonomously with your approval gate on. Platform members: add it as a task and approve who runs it.
Not a member yet?
Start with a free War Room on your real competitors and see your agents run a workflow like this end to end.