Recurring client invoicing: a checked billing list from Stripe

Stripe can generate invoices on its own for subscriptions, one invoice per billing cycle. If you bill variable work, the invoice is created by hand each month. The failure is rarely the invoice itself. The slip is the client you forgot, the retainer that changed amount, or the draft that sat unfinalized. A run sheet that compares this month with last month catches those before a client is billed late.

Stripe documents invoice statuses of draft, open, paid, void and uncollectible. Draft: still editable, so the sheet lists it as ready to finalize and flags it if it is still a draft after the day you set. Open: finalized and awaiting payment, counted as billed. Paid: counted as billed. Void: cancelled, so it does not count and the client is listed as missing. Uncollectible: counted as billed but noted for your attention. The job also flags amounts that moved more than a threshold you set.

You add the job and share a restricted Stripe key with read permissions. On the opening business day of each month a scheduled agent lists invoices from the previous period, builds the expected-billing list per customer, and compares it with invoices already created this month. It keeps currencies apart and never merges two customers who share a name. The output is one sheet: expected, present, missing and changed. It does not create, finalize, send or void anything in Stripe.

The COO agent runs the job on its schedule and, as department head, reviews the sheet before it reaches you: does every listed client exist in Stripe, are the amounts read from invoices rather than guessed, is any currency mixed. Then you approve, edit or skip it, and nothing is sent until you do. You create or finalize the invoices yourself in Stripe, with the list in front of you. The run takes the remembering out of billing day while the decisions stay with you.