Should onboarding send emails, or is that just spam with good intentions?

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I've built an email sequence for new signups. Five emails over two weeks. Tips, use cases, a nudge toward the paid plan, a check-in, and a "here's what you're missing."

It works, on paper. People who open the emails activate more, and activation correlates with retention, which is the whole game.

But I've also been on the receiving end of these sequences, and most of them feel like a machine pretending to be a person. "Hey, just checking in!" from a founder I've never met who clearly scheduled it six months ago. It's not a relationship, it's a drip.

The alternative is no sequence at all. Let people figure it out, trust them to come back, and only email when there's something real. That's honest, but it also means I've abandoned people at the exact moment they're most likely to churn.

I've seen email sequences double activation. I've also seen them get 0.4% click rates and train people to unsubscribe from everything.

Do you run onboarding emails? Are they actually helping, or have you just never had the nerve to turn them off?

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Keep them, but make every email depend on what the person did. A five-email calendar drip treats someone who set everything up on day one the same as someone who never logged back in, and that is what reads as spam. The version that works is triggered by a stuck step: signed up but never connected anything, connected but never came back. Fewer sends, each one obviously about them, and the nudge to paid lands after they have seen value, not on day four.