What does this automation do?
Nobody is emailed the day they cancel. A week later, once the decision has settled, an agent that knows the account writes one honest check-in and files the outcome.
What can you do with it?
- Leave a cancelling customer alone for the week that matters
- Reach out once, with context, instead of three times with a discount
- Keep a record of every winback attempt and how it went
The Steps
This automation runs in 5 steps:
- When Stripe — Canceled Subscription
- Then Delay — wait 7 days
- Then Taskade AI — Ask an agent ("Winback Desk")
- Then Gmail — Send Email
- Then Taskade — Add Task
What makes this different from a Zapier-style flow?
The "Winback Desk" step is not a one-off model call. It is a Taskade AI agent that knows your plans, usage history and past save offers, remembers every account it has already contacted, so every run builds on the last one instead of starting from an empty prompt.
A stateless "ask the model" step forgets everything the moment it returns. An agent keeps its knowledge and its memory between runs, carries its own tools, and can be handed work by other automations.
Who is this automation for?
Built for retention teams who know a same-day save attempt lands badly. Nobody is emailed the day they cancel. A week later, once the decision has settled, an agent that knows the account writes one honest check-in and files the outcome.
How do you set it up?
- Open the "Automations" tab in your workspace.
- Click ➕ Add automation, then start from scratch.
- Add the trigger "Canceled Subscription" from Stripe.
- Add a Delay step: Delay — wait 7 days.
- Add the action "Ask an agent" from Taskade AI. Point it at an agent called "Winback Desk".
- Add the action "Send Email" from Gmail.
- Add the action "Add Task" from Taskade.
- Enable the toggle in the top-right corner to activate the automation.
Prefer to describe it instead? Click Build this flow with AI above and Taskade wires the trigger, the steps, and the agent for you.