Customer Onboarding Plan

Onboarding has one job: get a new customer to the first thing that works for them, quickly, in their order, not the manual's. Customers who reach real value early tend to stay; customers who stall in the first weeks often never recover. You plan the path with them, keep both sides to their commitments, and notice when they go quiet before they give up. The standard: a first win the customer defined, a dated plan they have seen, check-ins that bring something useful, and a written graduation when it is done.

When to use

• "Acme just signed; set up their onboarding."
• "Write an onboarding plan template for new customers."
• "Northgate hasn't logged in since kickoff; what do we do?"
• "Which new customers are stuck?"
• A deal closes or a trial starts in the CRM (automate the trigger with cronjob if the owner wants).

What you need

• The sales handover, from the CRM (connected HubSpot, Salesforce, Pipedrive, Attio) and the deal notes:
  • what was sold and why, in the customer's words;
  • their goals and success measures from discovery;
  • stakeholders and their roles;
  • promises made (features, dates, service levels);
  • technical context and known risks. If anything is missing, ask the seller through ask_teammate before kickoff, not during it.
• Product usage data for the account if it exists: connected analytics such as PostHog or Mixpanel, the admin dashboard in the browser, or exports.
• The owner's standard onboarding steps, resources (help articles, videos, training) and who on the team can help with technical setup.
• The owner's connected calendar, for scheduling.

Method

1. Read the handover and fill the gaps. Write one paragraph on why this customer bought, in their words, and what success looks like to them. List every promise made in the sale; anything you cannot deliver goes to the owner now.
2. Choose the onboarding depth. The owner sets the line; record it in memory.
   • High-touch for larger or complex accounts: kickoff call, weekly check-ins, a named contact.
   • Lighter-touch for small accounts: a guided email sequence and a short welcome call, or emails only.
3. Define the first win with the customer. A specific, observable outcome tied to why they bought, reachable within days or a few weeks, with a target date.
   • Good: "First weekly schedule produced in the system for the Leeds site by the 14th."
   • Not good enough: "Account set up." This is the most important line in the plan.
4. Draft the success plan with references/success-plan-template.md:
   • the shared goal and the first win;
   • milestones by week, with dates;
   • commitments on both sides (what the customer must do, such as provide data or attend training; what we will do);
   • the check-in schedule and contacts on both sides;
   • what the customer can expect from us. Order the steps by the customer's goal, not by the product's menu.
5. Prepare the kickoff (30 to 45 minutes): introductions and roles; confirm goals and the first win; walk through the plan and adjust it together; agree who does what this week; book the next check-in before the call ends. Draft the invite and agenda for the owner's approval.
6. Run the check-ins. Weekly in the first month for high-touch, then every two weeks until graduation. Each check-in:
   • reviews the milestone table;
   • removes one blocker;
   • adds one useful tip based on what they are actually doing (look at their usage beforehand so you arrive with something specific). Draft the recap (progress, next steps, owners, dates) for approval after each one.
7. Watch for stalls with a daily or weekly cronjob check. Default triggers the owner can adjust:
   • no login or activity for 7 days during onboarding;
   • a milestone overdue by more than 3 business days;
   • two unanswered messages in a row;
   • the main contact leaves, changes role or goes on long leave;
   • support tickets showing confusion or frustration during setup. Act on the cause, not with "just checking in": a short, specific offer of help with the step they are stuck on; a 15-minute working session; another contact on their team who was at kickoff; or an adjusted plan. When a whole team has gone quiet, contact people individually rather than with one mass message. Tell the owner about any stall that lasts two weeks.
8. Confirm the first win when it happens. Celebrate it in a message to the customer (a draft), record the date, and calculate time to first value. Use the moment to agree the next goal.
9. Graduate. When the customer has hit the first win, finished the agreed milestones and uses the product regularly without help, write a graduation note: what was achieved, current usage, open items, risks, stakeholders and relationship, recommended next steps. Hand over to the account manager, and tell the customer who their contact is now (a draft for approval).
10. Learn across customers. Monthly: median time to first win, share of customers graduating within the target, where in the plan customers stall most, and the questions they ask most. Feed recurring questions into help articles and stuck steps into product feedback.

Worked example: a first win and a stall

• Customer: a 3-site freight firm that bought scheduling to cut planning time.
• First win agreed at kickoff: "Leeds publishes its first weekly rota from the system by 14 October."
• Day 6: no activity since the data import; their planner has not logged in. Usage shows the shift templates step was opened and abandoned.
• Response (draft for approval): "Hi Priya, I noticed the shift templates step can be fiddly the first time. Would a 15-minute session on Thursday help? We could build the Leeds templates together so the rota is ready for the 14th."
• Day 9: session held; templates built; rota published on day 12. Time to first value: 12 days.

Output

• The customer's success plan (a shared document), the kickoff agenda and the invite draft.
• Check-in recaps and stall-response drafts, each for the owner's approval.
• A tracker of all onboarding customers on a show_card: customer, start date, first-win target and status, next milestone, days since last activity, stall flags, owner.
• The graduation note for each customer.

Checks before you finish

• The first win is specific, tied to why they bought, and dated.
• Every promise from the sale is listed and either scheduled or raised with the owner.
• Both sides' commitments are in the plan, with dates.
• Stall triggers are set to run automatically.
• No message went to the customer without the owner's approval.

Pitfalls

• The product tour. Showing every feature in order overwhelms. Teach only what the first win needs.
• A plan only we have seen. Agree it with the customer, or it is a guess.
• Waiting for them to ask. Customers who are stuck usually go quiet rather than ask. Watch the data and reach out with something specific.
• Ignoring sales promises. A promise nobody delivers becomes the first complaint.
• Never graduating. Onboarding that drifts on for months hides a value problem. Graduate them or escalate.

See also: help-centre-article, churn-risk-signals, support-ticket-reply.