The five milestones

Milestone 1 — Account created

Email 1 fires. Welcome message, first three steps to set up the workspace, link to a 4-minute setup video. CTA: complete the workspace setup.

Milestone 2 — Workspace configured

Email 2 fires. Walks through the first real-data import. CTA: import your existing data. Users who hit this milestone within the first 48 hours retain at roughly 4x the rate of those who don’t.

Milestone 3 — First job created

Email 3 fires. The first useful action in the product. Email celebrates the milestone and points at the next layer of features.

Day 7 manual checkpoint

For users who haven’t hit milestone 2 by day 7, route to a CSM. The email is a real reach-out from a real person — “saw you got started but didn’t finish setup, want a 10-minute walkthrough?” Recovers 30 to 40 percent of stuck users.

Milestone 4 — First team member invited

Email 4 fires. The first team-collaboration email. Best practices for the role-based permissions, link to the admin guide.

Milestone 5 — First report run

Email 5 fires. The user has reached the “habit-forming” usage threshold. CTA shifts from “set up” to “level up” — advanced features, integrations, the customer community.