Square vs Stripe Billing

The small business savior that makes payments a breeze, but watch out for those sneaky fees meets the billing api that actually makes you want to charge customers, not dread it. Here's our take.

Square

Nice Pick

The small business savior that makes payments a breeze, but watch out for those sneaky fees.

Pros

• Dead-simple setup with no technical skills required
• All-in-one ecosystem from POS to payroll
• Transparent pricing with no long-term contracts

Cons

• Transaction fees can add up fast for high-volume sales
• Limited customization options for larger businesses

Stripe Billing

The billing API that actually makes you want to charge customers, not dread it.

Pros

• Handles complex subscription logic (metered billing, trials, prorations) with minimal code
• Seamless integration with Stripe Payments and other Stripe products
• Built-in invoicing, dunning management, and revenue recognition automation
• Developer-friendly API with clear documentation and predictable webhooks

Cons

• Pricing adds up quickly with transaction fees on top of Stripe Payments fees
• Lock-in effect: migrating away is painful once you're deep in Stripe's ecosystem

The Verdict

Use Square if: You want dead-simple setup with no technical skills required and can live with transaction fees can add up fast for high-volume sales.

Use Stripe Billing if: You prioritize handles complex subscription logic (metered billing, trials, prorations) with minimal code over what Square offers.

The Bottom Line

Square wins

The small business savior that makes payments a breeze, but watch out for those sneaky fees.