Direct answer
Onboarding breaks when teams automate everything or nothing. Map touchpoints into identical (automate) vs high-variance (human), run a 5–7 email behavior-triggered sequence, and escalate to CSM when milestones slip past N days.
Goal: ~70% less manual work while preserving high-touch moments that affect expansion and churn.
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List every onboarding touchpoint. Mark each as either 'identical for everyone' (automate) or 'unique per customer' (keep human).
5–7 emails over 14 days. Each email teaches one thing and ends with a single CTA. No greatest-hits compilations.
Trigger nudges off behavior, not time. Showing 'Try X' to someone who already tried X destroys trust faster than anything.
When an automation can't get a customer to the next milestone in N days, escalate to a CSM. Automation should know when to give up.