How many emails should a winback flow have?
Most winback flows work well with two to four emails spread over a few weeks. Stop once someone engages, and move people who still ignore every message into a sunset process rather than continuing to send.
A winback flow targets past customers who have not bought for longer than their usual repeat cycle. The first message can be a soft reminder, the next can show what is new, and a final message may carry an incentive if your margins allow.
More emails is not automatically better, because repeated messages to unengaged people raise unsubscribe and complaint risk. Set the delay by your average time between orders, not by a generic calendar.
Add an exit condition so anyone who orders or clicks leaves the flow immediately, and review results by revenue per recipient.
In practice.
A pet supplies store finds that customers usually reorder food every few weeks. Its winback flow starts only after that window has clearly passed, sends three emails over about two weeks, and exits anyone who places an order at any point.
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