Stop chasing late payments
“I spend hours every week looking through Quickbooks and emailing clients who haven't paid their invoices.”
Invoicing & Payments
Automate recurring billing, failed payment retries, and customer portals with Stripe
“We waste hours every month creating manual invoices, chasing declined credit cards, and updating client billing info.”
The short answer
Implement automated subscription billing and self-serve customer management using the Stripe API. Stripe automates recurring charges, calculates metered usage, sends automated receipts, and uses machine-learning Smart Retries to recover failed payments without staff intervention. Clients can upgrade plans or update expiring credit cards directly through a secure, self-service customer portal, eliminating involuntary churn and manual invoicing drag.
- ~4 hours/week back (estimated)
- 25 minutes to set up
- Easy difficulty
How we estimated that: Assumes ~4 hours a week previously spent issuing manual invoices, following up on expired credit cards, and processing card updates over the phone. This is a model, not a measurement — check it against your own numbers, because if the assumption does not match your business the figure will not either.
What you'll need
- Stripe free tier leanest paid option
Industry-standard payments and recurring subscription billing infrastructure.
Free until: Pay-as-you-go processing fees only (2.9% + 30¢ per successful card charge); zero monthly platform fee on standard tier.
Watch the pricing: Stripe Billing includes free tier for first $1M in lifetime volume, then 0.7% on recurring billing charges.
Pricing checked 2026-08-02 — source.
We are not paid by any tool listed here. If a cheaper or better option exists, that's what you'll see.
Pricing above was checked on 2026-08-02. Vendors change their terms without notice, and free tiers do get withdrawn. We take no money from any vendor listed here. If something on this page is out of date, tell us and we will correct it.
How to set it up
- Create Product and Recurring Pricing Tiers
Set up your recurring service plans (Monthly Maintenance, Retainer, Subscription) in the Stripe Dashboard with defined billing intervals.
- Enable Smart Retries and Automated Dunning Emails
In Settings > Billing > Retries, enable Smart Retries and turn on automated emails prompting customers to update failed payment cards.
- Configure the Stripe Customer Portal
Activate the hosted Stripe Customer Portal so clients can securely download PDF invoices, change billing details, and update payment cards self-serve.
- Connect Payment Webhooks to Your System
Listen for `invoice.paid` and `customer.subscription.deleted` webhooks to automatically provision client access or notify your account manager.
Common questions
- How does Stripe prevent customer churn from expired credit cards?
- Stripe works directly with card networks to automatically update expired card numbers and CVVs in the background, preventing payment interruptions.
- Can customers manage their own billing without calling our office?
- Yes. The Stripe Customer Portal allows clients to view past receipts, update credit cards, or change subscription plans securely on their own.
- Is our business liable for storing credit card information?
- No. Stripe securely tokenizes and stores all sensitive card data in PCI-DSS Level 1 certified vaults; your servers never touch raw card numbers.
Last reviewed 2026-08-04. Tools change — if something here is out of date, tell us and we'll fix it.
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