What are “winback” vs “retention” segments?

Retention segments contain active relationships you're trying to maintain. Winback segments contain lapsed relationships you're trying to revive.

Retention targets people who are currently engaged but might drift. The goal is preventing decay. You're reinforcing value, encouraging deeper engagement, and addressing early warning signs before they become problems.

Winback targets people who were engaged but stopped. The goal is reactivation. You're trying to reignite interest, remind them of value, or at least learn why they disengaged.

The timing determines which applies:

Someone who engaged last week and skipped two emails? Retention. Normal variation, keep nurturing.

Someone who hasn't engaged in 90 days despite continued sending? Winback territory. The relationship has cooled.

Retention messaging can be subtle. You're maintaining rhythm, not sounding alarms. Winback messaging needs to be more direct. Acknowledge the absence. Offer a reason to return. Sometimes ask explicitly: \"Do you still want to hear from us?\"

Track movement between these segments. Ideally, retention prevents people from ever needing winback. But some decay is inevitable, and having a clear winback strategy catches those who slip through.