#214 · Deposits Deliveries & Guarantees: Advanced AI Agency Pricing

youtube ↗Sales

How do you handle recurring retainer payments and invoicing with Stripe, and what tools do you use for proposals and sales workflow?

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.

stripe invoicingproposal generatormake.com

Related answers

youtube ↗Agency Operations

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.

stripeinvoicingautomation
youtube ↗AI & Automation

How can I set up an automated invoice‑collection system for my agency, and how should I sell it to clients?

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.

invoice automationgoogle sheetsstripe
youtube ↗Pricing

How do you monetize workflow‑automation services? Should I use subscriptions, Stripe, or other payment methods?

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.

monetizationaffiliatesubscription
youtube ↗Sales

After gaining a client, how do you get the contract and transfer payment? Is it via Stripe?

It's straightforward and depends on the platform. On Upwork they handle payments, escrow, and invoices, so beginners don't need Stripe or a business account. Otherwise, ask the prospect for a fixed-price or hourly offer based on your negotiation; you can split payments into milestones (e.g., 50% up front, 33% each). The prospect creates an offer, you accept, and the money goes into escrow—a neutral account that releases funds when you submit the agreed deliverables. To reduce drop-off, combine the proposal, contract, and invoice into one document after the sales call; the client signs, a payment page appears, and after the invoice you receive an email booking the onboarding call. This cuts the funnel loss from ~40% to ~20%. US companies tend to move faster through this process than European ones, which often require more steps.

paymentcontractupworkescrow