Payments & Billing
Charge customers via one-time purchases, subscriptions, or usage-based billing.
Options
Billing Model*
Payment Processor*
Decision Points
Is the revenue model recurring (SaaS)?
If yes
Choose subscription billing. Evaluate usage-based if pricing scales with consumption.
If no
One-time purchase is far simpler. Consider Stripe Checkout for a no-code option.
Is global VAT/sales tax compliance a concern?
If yes
Use Paddle as merchant of record — they handle tax across jurisdictions.
If no
Stripe gives more control; integrate TaxJar or Stripe Tax if needed later.
Do you want to offer a free trial without requiring a card upfront?
If yes
Use reverse trials — free-tier access with a prompt to add a card at the end. Higher signup conversion but lower trial-to-paid conversion.
If no
Card-required trials filter out tire-kickers and produce 2–3x higher trial-to-paid rates. Stripe supports both via checkout.
Do you sell to enterprise customers with procurement processes (POs, net-30 terms)?
If yes
Support invoicing workflows (Stripe Invoicing or manual PDF invoices via finance). Self-serve credit-card checkout is insufficient at that ACV.
If no
Credit-card-only is simpler and covers all SMB/prosumer use cases.
Do you sell in markets where customers transact in non-USD currencies?
If yes
Enable multi-currency pricing in Stripe or Paddle. Price in local currency — EU/UK customers strongly prefer EUR/GBP over USD conversions.
If no
USD-only is simpler; add currencies only when a market demands it.
Will you close large B2B deals that need ACH or wire transfer (>$5k)?
If yes
Enable Stripe ACH Credit Transfer or wire instructions on invoices. Credit-card fees on large invoices are prohibitive.
If no
Card-only is fine for SMB and prosumer ticket sizes.
Do you have EU customers (SCA/3DS compliance required)?
If yes
Use Stripe Payment Intents (handles 3DS authentication automatically) or Paddle. Do not use raw Charges API — it predates SCA.
If no
Still use modern Payment Intents API — SCA will apply to US processors eventually.
Is self-serve cancellation acceptable, or do you need "contact us to cancel"?
If yes
Self-serve cancellation via Stripe Customer Portal — legally required in California (FTC Click-to-Cancel) for many subscriptions.
If no
Contact-us friction increases short-term retention but damages NPS and is increasingly regulated. Think twice.
Do marketing or sales teams need to issue coupons and discounts?
If yes
Use Stripe Coupons / Paddle Discounts. Support percentage and fixed-amount discounts with expiry and redemption limits.
If no
Skip — discount UX adds complexity and is rarely needed outside marketing-led motions.
Do users frequently upgrade/downgrade mid-cycle?
If yes
Enable proration in Stripe (proration_behavior: create_prorations). Immediate upgrade + end-of-period downgrade is the customer-friendly pattern.
If no
Wait-until-renewal plan changes are simpler; skip proration logic.
Do you have >1000 paying customers or expect significant failed-payment volume?
If yes
Enable Stripe Smart Retries (free) plus a custom dunning email sequence (day 0, 3, 7, 14). Recovers 30–50% of failed payments.
If no
Default Stripe retries are enough; add custom dunning once failed payments become a meaningful revenue leak.
Should customers manage their own billing (payment methods, invoices, plan changes)?
If yes
Use Stripe Customer Portal or Paddle Retain — pre-built UI, handles tax/invoices/cancellation. Massive support-ticket reducer.
If no
Build a minimal billing page and route the rest to support — only viable at low customer counts.
Do you connect buyers and sellers and need to split payments (marketplace)?
If yes
Use Stripe Connect (Standard or Express accounts). Do not build split payments yourself — tax forms, KYC, and payouts are legal minefields.
If no
Standard direct charges are simpler and correct for first-party sales.
Do you need to issue refunds regularly with reason tracking and approval flows?
If yes
Build an internal refund tool that captures reason, links to audit log, and uses Stripe Refunds API. Required for support scale and compliance.
If no
Manual refunds through the Stripe dashboard are fine until volume demands tooling.
Are you tempted to store raw card numbers to avoid re-entry (PCI Level 1 scope)?
If yes
Do not. Use Stripe Payment Methods or Paddle saved cards — tokenized references keep you out of PCI DSS Level 1 scope. The compliance overhead is massive.
If no
Good — always tokenize. Stripe Elements, Paddle Checkout, or hosted checkout keeps card data off your servers entirely.
Tradeoffs
Requires handling trial periods, dunning, proration, and cancellation flows
Must instrument every billable action and send metered events to billing provider
Less customizable checkout; Paddle acts as legal seller so you avoid VAT registration