A 5-person startup and a 200-person enterprise need different onboarding paths. The agent supports configurable milestone tracks by customer segment — company size, plan tier, primary use case, or any CRM attribute. Each track defines the specific product events that constitute a successful onboarding: account setup, first integration connected, first workflow triggered, first team member added, first successful export or sync. Milestone completion is tracked from product event streams — not self-reported. Customers see their own progress; CSMs see progress across their entire book. No spreadsheet, no manual status update, no guesswork about where each customer stands.

A significant portion of onboarding CSM time goes to tasks that could be automated without any loss of quality: sending the integration setup guide the day after account creation, scheduling the kickoff call 48 hours post-signup, sending the 'your first week checklist' email when setup is complete, logging milestone completions to the CRM, and creating CSM tasks when a customer hits a specific step. The agent handles all of these automatically so CSM time is reserved for the conversations that require human judgment — not the administrative work of routing guides and logging updates. Automation coverage is configurable; teams can define exactly which steps are automated and which require CSM involvement.

Stall detection is the highest-value function in automated onboarding. The agent compares each customer's progression against the segment cohort benchmark — not a theoretical ideal, but the actual median time for customers in the same segment to complete each step. When a customer is behind the median by a configurable threshold (e.g., 50% beyond median time at a given step), the CSM receives an intervention alert with a specific recommended action: send a targeted guide, schedule a live troubleshooting call, escalate to the technical team. The alert includes context about which step they're stuck on and the most common reasons customers stall at that step — so the CSM can address the likely cause, not just check in generically.

Onboarding success is measured by one thing: how quickly customers reach their first meaningful value milestone — the moment they get the outcome they signed up for. The agent tracks time-to-value for every customer and cuts it by segment, CSM, plan tier, and onboarding track. Completion rates, average time-to-value, and stall frequency by step are reported at both the individual account level and the cohort level. When a specific step is causing disproportionate stall across the cohort, that's a product or documentation problem — the agent flags it for the product and CS leadership teams so it gets addressed at the root, not just at the individual account level.