Assisted onboarding plan generator (L2)
A shared assistant workspace turns the signed order form and kickoff notes into a 30, 60, 90 day onboarding plan with owners and milestones. The CSM edits rather than starts from a blank template, and every plan comes out in the same shape.
The steps
- 01
Codify the milestone model
Tool: Notion
Write down what a good onboarding actually contains for your product: technical setup, first value event, admin training, rollout, executive review. The assistant cannot generate a model you have never written down. Owner: CS leader. DoD: the milestone model exists as one page.
- 02
Build the shared project
Tool: Claude
Load the milestone model, three strong past plans, and the product implementation guide into a shared assistant project so every CSM generates from the same context. Owner: CS ops. DoD: project is shared with the whole CS team, not one power user.
- 03
Generate at kickoff, edit in the tool of record
Tool: Gainsight
Plan is generated within 24 hours of kickoff, then pasted into the customer success platform as the live plan. The generated doc is a draft, never the system of record. Pitfall: plans living in chat history where nobody tracks them. DoD: every new account has a plan in the platform inside one week.
- 04
Review edit distance monthly
Tool: Manual
Sample five plans and mark how much the CSM rewrote. Heavy rewriting in the same section means the milestone model is wrong, not the model output. Owner: CS leader. DoD: monthly note listing the section that gets rewritten most, and the fix.
Tools in this playbook
Next playbooks
Unfamiliar terms are defined in the AI and Revenue Dictionary. Related frameworks live in the framework library.