SimplyBills lets a connected AI draft reminders for overdue invoices

The task

The post is addressed to self-employed people who work alone and notice unpaid invoices late. Chasing payment follows stages: a friendly reminder, a first dunning letter, and a second one, and each message needs a tone that suits the customer. Going through the open items every morning and wording each message is the routine work the post proposes to hand to an AI assistant.

What they did

The user connects an AI assistant they already use, ChatGPT or Claude, to SimplyBills through its AI interface (MCP). SimplyBills does not build in an assistant of its own. The assistant reads invoice and payment data. The user asks which invoices are overdue, and the assistant lists invoices about to fall due and invoices already overdue, sorted by days and amount, and points out patterns such as customers who often pay late. The user then asks for a reminder for the oldest overdue invoice and says which tone to use, for example relaxed, factual with a new payment date, or formal. The assistant can also read a customer's payment history and choose the tone itself. The user reads the text and adjusts a word where needed.

Where the approval sits

The source says nothing goes out without the user's confirmation, including friendly reminders. Before any send, SimplyBills returns a summary of the message and its recipient to the assistant, which then has to ask the user. According to the source, this check runs on the server and cannot be bypassed with a chat instruction. On the Pro plan the assistant only saves a draft, and the user presses send in SimplyBills. Sending through the assistant requires the Max plan and still needs the confirmation. The assistant does not hand an invoice to a collections agency; that decision stays with the user.

Worth knowing

The source is SimplyBills' own blog post and also promotes its plans, so it describes a setup and reports no results from a real customer. The morning routine and the sample letters in it are illustrations. The post also describes rule-based reminders in the Pro plan that can run automatically without a release for each message; this entry covers only the assistant layer, where a person confirms each send. The post's sections on dunning stages and interest are left out. For context: when a debtor who is not a consumer is in default, section 288(5) of the German Civil Code (BGB) also gives the creditor a flat fee of EUR 40. This is not legal advice.

Prompt for your agent

More in this category

• Invoices and payment reminders

  A consultant drafts late invoice follow-ups with AI and sends them

  A consultant uses ChatGPT or Claude to draft a three-step series of follow-up emails for late invoices, saved as templates. The consultant adds the client details and sends each email personally from their own mailbox.

  Read the entry
• Invoices and payment reminders

  easybill lets an AI assistant draft invoices and wait for approval

  easybill's help article describes a connector that lets an AI assistant create invoices, quotes, and credit notes in an easybill account. Each document starts as a draft, and finalizing, sending, and recording payments wait for the user's confirmation.

  Read the entry