What invoicing software is best for an automation agency that needs recurring invoices and late payment reminders?
I use Stripe for everything. My guiding principle is always ‘keep it simple, stupid’—I want as few platforms as possible, and the automation I build on those platforms should also be simple. Stripe gives me AI-powered features and API endpoints for every need, so I don’t have to resort to hacky workarounds. It handles recurring billing, late‑payment reminders, and integrates smoothly with the rest of my stack, making it the best all‑in‑one solution for my automation agency.
The invoice reminder is sent from your own business email—the same one you use for regular communication—so customers recognize your domain (e.g., nickleclick.ai) and assume legitimacy. To pull overdue invoices you can use Stripe, QuickBooks, Zero, or any major invoicing tool to retrieve all invoices sent up to a point (e.g., the last 100) and apply the same logic: filter for unpaid, calculate overdue amounts, and send reminders.
For recurring retainer payments, I rely on Stripe’s built‑in subscription/invoicing feature: create a customer, attach a recurring product to an invoice, and send it. I don’t need a fancy automated system—manually putting together an invoice takes about 30 seconds and is worth it. For the sales workflow, I use a simple form during calls to capture the customer’s name, email, phone, business, and problem details. That form triggers a make.com workflow that feeds the data into AI, which populates a proposal template on platforms like Panadoc, Better Proposals, or Quiller. Panadoc is handy because it includes payment integration that handles Stripe, though its API cost is high ($2 per document). The overall process is: sales call → form → make.com → AI‑filled proposal → send to client. You don’t need to build a custom widget or workflow; the existing tools are sufficient.
The automation works by using a Google Sheet as a simple database of invoices you’ve sent. For each invoice you record the date, then calculate how many days have passed. Based on the age you trigger follow‑up emails: after 7 days send follow‑up A, after 14 days send B, and so on (7, 14, 21, 28, 35, 42 days). The sheet can be built in any system you prefer—Google Sheets, a CRM, Stripe, QuickBooks, etc.—as long as you can pull the invoice date and payment status. A second automation watches for incoming payments (e.g., via Stripe) and marks the invoice as paid, so only unpaid invoices continue to receive follow‑ups. The email templates are simple reminder messages that reference the invoice and ask if the client needs anything to expedite payment. This low‑cost setup automates the entire follow‑up process without manual effort.
There are several ways. One is to sell courses that teach specific enterprise tools—think Airtable or Zapier for large companies—usually priced around $100. Another is affiliate revenue: by embedding affiliate links you can earn an extra 5‑10 % on each client you refer, which can boost agency margins from about 30 % to 40 %. Over a client’s lifetime that can add roughly $10‑$15 per month per client, scaling to several hundred dollars per year per client. You can also run monthly subscription models on a cloud server, using payment processors like Stripe to handle recurring billing. I’m planning a video that walks through setting up an AI‑automation agency from day one, covering all these monetization streams.