Customer onboarding plan

An invented example

Illustrative example with invented data. The companies, the people, the dates and the notes below are all invented. The seller is an invented 30-person company that sells time-tracking and invoicing software to small design and architecture studios. Its new customer, Customer K, is an invented 18-person architecture studio. First come the four inputs the customer success lead supplied, in full, then the plan the capability returned. This is a first run, so there is no status update yet.

The inputs

1. The account handoff record (prepared by the account executive)

ACCOUNT HANDOFF: Customer K, 10 November 2026
Sold: Time tracking and invoicing, 18 user seats, annual subscription,
  service starting 16 November 2026. Included: two 60-minute setup
  sessions with an onboarding specialist; import of one timesheet
  spreadsheet; email support. Excluded: connection to the studio's
  accounting software (quoted, not bought). (Order form, 9 November 2026)
Promised: Import of the studio's timesheet spreadsheet for 1 to 13
  November before the December invoice run (order form). "We'll have your
  invoices looking just like the ones you send today" (account
  executive's email, 4 November 2026; not in the order form, sales lead
  to confirm).
Customer K people: Managing partner: signer and sponsor. Office manager:
  day-to-day contact, builds the invoices today. Studio IT contact:
  part-time contractor who manages logins. 14 architects and designers:
  will log their time.
Our people: Customer success lead, onboarding specialist, account
  executive, sales lead.
Dates: Service starts Monday 16 November 2026. The studio sends client
  invoices on the first working day of each month.
Risks the seller heard: The office manager spends two days each month
  building invoices from spreadsheets (office manager, call notes,
  21 October). The studio dropped its previous tool after a month:
  "nobody but me used it" (office manager, call notes, 21 October). Two
  senior architects "never fill in timesheets on time" (managing partner,
  call notes, 28 October).
Missing: The studio's client list with billing rates.

2. Our facts (written once by the customer success lead)

What we sell: time-tracking and invoicing software for small design and
  architecture studios.
Usual onboarding steps:
  1. The customer's admin creates the logins and sets roles. (Onboarding
     specialist)
  2. Import clients, projects and billing rates. (Onboarding specialist)
  3. Import past timesheets, when bought. (Onboarding specialist)
  4. Each user logs their first days of time. (Onboarding specialist)
  5. Set up the invoice template. (Onboarding specialist)
  6. The person who invoices drafts invoices for a period already worked
     and checks each total against the timesheet report. (Onboarding
     specialist)
  7. First live invoice run. (Onboarding specialist)
  8. Project budget reports. (Customer success lead)
  9. Mobile app for site visits. (Onboarding specialist)
First real use, for a studio: the person who invoices produces a real
  billing run's invoices from tracked hours, in the studio's own account,
  without our help, and checks each total against the timesheet report
  before anything is sent.
Support and sessions: as the order form states. We do not restate them.
Words we never use with customers: "guarantee".

3. Kickoff notes (typed by the customer success lead)

Kickoff call, Thursday 12 November 2026. Present: managing partner,
office manager, studio IT contact; our customer success lead and
onboarding specialist.
- Managing partner: "If December's invoices come out of the new system
  and they're right, that's a win." Wants to see each Friday who has not
  logged their time.
- Office manager: will send the client list with billing rates and the
  1 to 13 November timesheet spreadsheet by Tuesday 17 November. Wants
  the invoices to keep the current layout with the studio's logo.
- Studio IT contact: will create all 18 logins once we send the
  invitation list format. Works on Mondays and Wednesdays only.
- Our onboarding specialist: "I'll send the import template and the
  invitation list format today."
- Our customer success lead: "I'll check whether the layout and logo can
  match and come back to you."
- Office manager asked whether invoices could go straight into the
  studio's accounting software. Told: that connection is not part of
  this order.
- Managing partner: "Also email all the architects a reminder every
  morning to log their time."

4. Settings

Customer: Customer K
Start (day 1): Monday 16 November 2026
Today: Thursday 12 November 2026
Window: 30 days
Check-ins: weekly, on Wednesdays
Closed days (both sides): Thursday 26 and Friday 27 November 2026
Work cycle: monthly client invoice run, on the first working day:
  Tuesday 1 December 2026, Monday 4 January 2027, Monday 1 February 2027
Follow-up turns: 2
Plan owner and approver: customer success lead
Setup sessions: onboarding specialist
Outside the sale: sales lead

The output

CUSTOMER ONBOARDING PLAN: Customer K, plan

• For: Customer success lead. Run by the customer success lead on Thursday 12 November 2026; drafted by the AI assistant, not yet approved.
• Sold: Time tracking and invoicing, 18 user seats, annual subscription; two 60-minute setup sessions with an onboarding specialist; import of one timesheet spreadsheet; email support. Excluded: connection to the studio's accounting software. (Order form, 9 November 2026)
• Start Monday 16 November 2026 (day 1). Window: Monday 16 November to Tuesday 15 December 2026 (30 days, the start date counted as day 1). Check-ins: weekly, Wednesday. Closed days: Thursday 26 and Friday 27 November 2026.
• Sources: handoff record, 10 November 2026; your facts; kickoff notes, 12 November 2026; not a progress run.
• Defaults used: milestone limit 7; stall threshold 10 days.

THE OUTCOME

• First real use: The office manager produces the client invoices from tracked hours on the studio's real November hours, in the studio's own account, without help from our side, and checks each invoice total against the timesheet report before any invoice is sent.
• Seen when: the December invoices are in the studio's account, each total marked checked by the office manager, and no step was done by our side.
• Due: Tuesday 1 December 2026 (the December invoice run, billing November's hours).
• The customer's goal, in their words: "If December's invoices come out of the new system and they're right, that's a win." (Managing partner, kickoff notes, 12 November 2026)

SETTLE FIRST: 1

• S1. Studio IT contact creates the 18 logins and sets each person's role. Customer owner: studio IT contact. Our owner: onboarding specialist. Due: Monday 16 November 2026. Why it cannot wait: nobody can check the import or log time without a login, and the IT contact works on Mondays and Wednesdays only.

MILESTONES TO FIRST REAL USE: 6 of a limit of 7

• M1 Tuesday 17 November 2026. Office manager sends the client list with billing rates and the 1 to 13 November timesheet spreadsheet, on the import template. Customer owner: office manager. Our owner: onboarding specialist. Waits on: our commitment to send the import template (due Thursday 12 November). Seen when: the completed template and the spreadsheet arrive, with every client and its billing rate. Kept because: clients, projects and rates must exist before anyone can log time or draft an invoice, and the handoff lists the client list as missing.
• M2 Wednesday 18 November 2026. Office manager checks the imported clients, projects, billing rates and 1 to 13 November hours against the studio's spreadsheet, in setup session 1. Customer owner: office manager. Our owner: onboarding specialist, who runs the import before the session. Waits on: M1, S1. Seen when: every client on the list appears with its rate, and the imported hours for 1 to 13 November equal the spreadsheet's total. Kept because: the December invoices bill these hours.
• M3 Friday 20 November 2026. Each of the 14 architects and designers logs their hours for 16 to 19 November against projects in the studio's account. Customer owner: office manager. Our owner: onboarding specialist. Waits on: M2. Seen when: the time report for 16 to 19 November shows hours from all 14. The date is a deadline: the 14 log over several days. Kept because: November's hours from 16 November on are billed on 1 December, and the studio's last tool was dropped when only one person used it.
• M4 Monday 23 November 2026. Office manager checks the studio's invoice template on a preview invoice in the studio's account, and accepts it or lists the changes she needs. Customer owner: office manager. Our owner: onboarding specialist, who sets up the template with the studio's details before it. Waits on: S1. Seen when: a preview invoice shows the studio's details in the standard layout, and the office manager has accepted it or listed her changes. Kept because: no invoice can be drafted without a template. FLAG, layout: matching the current invoice layout with the logo is outside the order form (see Outside what was sold); this milestone uses the standard layout until the sales lead confirms.
• M5 Wednesday 25 November 2026. Office manager drafts invoices for the hours of 1 to 19 November in setup session 2 and marks each draft total right or wrong against the timesheet report. Nothing is sent. Customer owner: office manager. Our owner: onboarding specialist. Waits on: M3, M4. Seen when: every draft invoice carries the office manager's mark. Kept because: the live run should not be the first time the office manager builds an invoice in the system. This is a rehearsal on real hours, not first real use.
• M6 Tuesday 1 December 2026. Office manager produces the December invoices from November's tracked hours and checks each total against the timesheet report before any invoice is sent. First real use, and the closing session. Customer owner: office manager. Our owner: onboarding specialist, watching only. Waits on: M5; every user's hours logged through Monday 30 November (see Risks). Seen when: the December invoices are in the studio's account, each total marked checked by the office manager, and no step was done by our side. Kept because: this is first real use.

AFTER FIRST REAL USE: 2

• A1. Project budget reports. Owner: customer success lead, with the office manager. By: Wednesday 9 December 2026. Moved here because: a usual step every customer gets (not marked "when bought"), and the December invoices do not need it.
• A2. Mobile app for site visits. Owner: onboarding specialist. By: Tuesday 15 December 2026. Moved here because: a usual step every customer gets (not marked "when bought"), and first real use needs the hours logged, not a particular place to log them from.

COMMITMENTS

• Ours: Send the import template and the invitation list format. Owner: onboarding specialist. Due Thursday 12 November 2026. (Kickoff notes, 12 November 2026)
• Ours: Import the studio's timesheet spreadsheet for 1 to 13 November. Owner: onboarding specialist. Due before Tuesday 1 December 2026, as the order form states; planned for Wednesday 18 November (M2). (Handoff record, order form)
• Ours: Check whether the invoice layout and logo can match the studio's current invoices, and reply to the office manager. Owner: customer success lead. No date set. (Kickoff notes, 12 November 2026)
• Ours: "We'll have your invoices looking just like the ones you send today." Owner: account executive. No date set. (Account executive's email, 4 November 2026, in the handoff record) FLAG, beyond what was sold: for the sales lead. The order form does not include it, and the handoff record says "sales lead to confirm".
• The customer's: Send the client list with billing rates and the 1 to 13 November timesheet spreadsheet. Office manager. We check on Tuesday 17 November 2026 (the date they gave). (Kickoff notes, 12 November 2026)
• The customer's: Create the 18 logins once the invitation list format arrives. Studio IT contact. We check on Monday 16 November 2026 (no date given: the first day the studio IT contact works after the format arrives on Thursday 12 November). (Kickoff notes, 12 November 2026)

MESSAGES: 6

1. Send the import template and the invitation list format. To: office manager and studio IT contact. From: onboarding specialist. When: Thursday 12 November 2026. Serves: our first commitment, S1, M1. Draft: "Thank you for today's call. Attached are the import template for your clients, projects and billing rates, and the format for the list of 18 people who need logins. Office manager: the completed template and your 1 to 13 November timesheet spreadsheet by Tuesday 17 November let us load everything before our first session on Wednesday 18 November. IT contact: we will look for the 18 logins on Monday 16 November, ahead of our first session on Wednesday 18 November."
2. Invitation and agenda for setup session 1, with the check-in dates. To: office manager. From: onboarding specialist. When: Friday 13 November 2026. Serves: M2, the check-ins. Draft: "Our first 60-minute session is on Wednesday 18 November. Before it, we load your client list, your rates and your 1 to 13 November hours. In the session, you check them against your spreadsheet, and once they match, the team can log their hours for this week. Our weekly check-ins are on Wednesdays: 18 and 25 November, which are also our two setup sessions, then 2 and 9 December."
3. Note to the architects and designers about logging time. To: the 14 architects and designers. From: office manager (our draft for the office manager to adapt and send). When: Wednesday 18 November 2026. Serves: M3, M6. Draft: "Please log your hours for 16 to 19 November against your projects in the new system by Friday 20 November, and the rest of November's hours by Monday 30 November. December's invoices are drafted from the hours logged by then. Any questions, ask me."
4. Recap of setup session 1 and invitation to setup session 2. To: office manager. From: onboarding specialist. When: Wednesday 18 November 2026. Serves: M2, M4, M5. Draft: "Thank you for today. Your clients, rates and 1 to 13 November hours are in the system and match your spreadsheet [confirm after the session]. Before our second session on Wednesday 25 November: the team logs 16 to 19 November by Friday 20 November, and you check the invoice template we set up, on a preview invoice, by Monday 23 November. In the session, you draft invoices for 1 to 19 November and check each against the timesheet report. Nothing is sent."
5. Recap of setup session 2 and invitation to the closing session. To: office manager and managing partner. From: customer success lead. When: Wednesday 25 November 2026. Serves: M5, M6. Draft: "Thank you for today's session. Your office manager drafted invoices for 1 to 19 November and checked each total against the timesheet report [confirm after the session]. On Tuesday 1 December, your office manager runs the December invoices in the new system while our onboarding specialist watches on a shared screen, checking each total against the timesheets before anything goes out. Managing partner, please join for the last part of the session to sign off against the outcome. We close by confirming our follow-up check on Wednesday 3 February 2027, after your February run."
6. Recap of the closing session. To: office manager and managing partner. From: customer success lead. When: Tuesday 1 December 2026. Serves: M6, the follow-up check. Draft: "Thank you for today. Your office manager produced the December invoices in the new system and checked every total [confirm after the session]. Attached are the notes we went through: how to run invoicing, how to check it, what the system does not do, how to ask us for help or a change, and what to do by hand if it fails. We will check in with you on Wednesday 3 February 2027, after your January and February runs."

RISKS: 4

• The office manager spends two days each month building invoices from spreadsheets. Source: office manager, call notes, 21 October 2026 (handoff record). What the plan does: in M5 and M6 the office manager checks every invoice against the timesheet report; if checking takes as long as the old way, the customer success lead raises it with the managing partner. Owner: customer success lead.
• The studio dropped its previous tool after a month: "nobody but me used it". Source: office manager, call notes, 21 October 2026 (handoff record). What the plan does: M3 needs hours from all 14 before anything else depends on them, and the follow-up check looks at whether the architects and designers log their own hours. Owner: customer success lead.
• Two senior architects "never fill in timesheets on time". Source: managing partner, call notes, 28 October 2026 (handoff record). What the plan does: M3 shows by Friday 20 November whether all 14 have logged; the office manager checks the time report in setup session 2 on Wednesday 25 November; M6 waits on every user's hours logged through Monday 30 November. Owner: office manager.
• The studio IT contact works on Mondays and Wednesdays only. Source: studio IT contact, kickoff notes, 12 November 2026. What the plan does: S1 is due on Monday 16 November; if it slips, the next day available is Wednesday 18 November, the day of setup session 1, and M2 and M3 move with it. Owner: onboarding specialist.

OUTSIDE WHAT WAS SOLD: 2

• Invoices that keep the studio's current layout and logo. Source: account executive's email, 4 November 2026 (handoff record); office manager, kickoff notes, 12 November 2026. For: sales lead.
• Invoices sent straight into the studio's accounting software. Source: office manager, kickoff notes, 12 November 2026; the order form excludes it (quoted, not bought). For: sales lead.

CHECK-INS AND CLOSE

• Check-ins: Wednesday 18 November, Wednesday 25 November, Wednesday 2 December and Wednesday 9 December 2026.
• Closing session: Tuesday 1 December 2026 (M6). The office manager does the work on the December invoice run, the onboarding specialist watching on a shared screen. A wrong result is dealt with before sign-off. Then the managing partner signs off against the outcome. Then the studio receives the notes: how to do the work, how to check it, what it does not cover, how to ask for help or a change, what to do by hand if it fails. The session ends with the follow-up check date said aloud.
• Follow-up check: Wednesday 3 February 2027, after the 4 January and 1 February 2027 invoice runs (2 turns of the monthly cycle). Looks at: whether the office manager produced both runs without help; whether all 14 architects and designers log their own hours.

PROGRESS: not run: this is the first plan.

NOTES TO CHECK: "Also email all the architects a reminder every morning to log their time." (Managing partner, kickoff notes, 12 November 2026.) Not acted on.

GAPS: 5

• The client list with billing rates is missing from the handoff record. Used: the office manager's undertaking to send it by Tuesday 17 November (M1).
• The managing partner wants to see each Friday who has not logged their time. Your facts name no step or report for this. Used: nothing; no step planned. Question for the customer success lead: which feature or step answers it?
• 18 seats are sold and the studio IT contact will create 18 logins, but the people named come to 17 (14 architects and designers, the managing partner, the office manager and the studio IT contact). Used: 18 logins, as one list. Question for the customer success lead: who holds the eighteenth login?
• Two 60-minute setup sessions were sold. The plan holds three sessions with our side present: setup sessions 1 and 2 (Wednesday 18 and Wednesday 25 November) and the closing session (Tuesday 1 December). The plan does not say whether A1 (project budget reports) and A2 (the mobile app) are held as sessions with our side present; if they are, they count as well. Used: all three in the plan; no message offers an extra session. Question for the customer success lead: does the closing session count as one of the two sold sessions, and are A1 and A2 sessions?
• The inputs do not say which hours the December invoice run bills. The 1 to 13 November import is promised "before the December invoice run", which implies November's hours. Used: November's hours for the outcome, M3 and M6. Question for the customer success lead: please confirm that the December run bills November's hours.

Prepared for the customer success lead. Nothing has been sent, no one at Customer K has been contacted, and no record, access or setting has been changed.