The core difference
Stripe is API-first. It was built for developers and online businesses, and it shows in everything from its documentation to its dashboard. If you want to build a custom checkout flow, run a SaaS business with subscription billing, or operate a marketplace where multiple sellers get paid, Stripe is genuinely excellent. It requires technical setup to use fully. That is not a criticism — it is by design.
Square is hardware-first. It was built for in-person businesses that want to accept payments without hiring a developer. A retail shop, a food truck, a hair salon — Square gives you a free card reader, a full POS system, and inventory management before you spend a dollar. No engineer required.
The philosophical difference matters: Stripe gives you payment infrastructure you can build anything on top of. Square gives you a complete business operating system for in-person selling.
"Pick Stripe if you need a developer. Pick Square if you don't want to need one."
Quick comparison: Stripe vs Square
| Feature | Stripe | Square |
|---|---|---|
| Processing fee (online) | 2.9% + 30¢ | 2.9% + 30¢ |
| Processing fee (in-person) | 2.7% + 5¢ | 2.6% + 10¢ |
| Monthly fee | Free on base plan | Free on base plan |
| Hardware | Terminal ($59–$349) — smaller selection | Free reader to $799 terminal — full ecosystem |
| POS software | Basic | Full POS with inventory, staff, reporting |
| Subscriptions / recurring | Stripe Billing — excellent | Available but less flexible |
| API / integrations | Best in class | Solid but less developer-focused |
| International payments | 40+ countries | US, Canada, UK, AU, JP, IE |
| Dispute handling | Similar to Square | Similar to Stripe |
| Best for | Online, SaaS, developer-led businesses | Retail, restaurant, in-person service |
Stripe — deep dive
Stripe's documentation is the gold standard. Full stop. It is the first thing developers reach for when they need to add payments to an application, and it has been that way for over a decade for good reason: the API is clean, the docs are thorough, and the error messages are actually useful.
Beyond basic payment processing, Stripe Billing handles subscriptions, trials, proration, and dunning (automatic retry sequences for failed payments) with a level of configurability that Square's subscription tools cannot match. If you run any kind of recurring revenue business — software, membership, retainer — Stripe Billing is worth evaluating on its own.
Stripe Connect is the product that powers payments for platforms and marketplaces: tools where money flows to multiple parties. If you are building something where your customers need to get paid through your platform, Stripe Connect is purpose-built for it.
In-person via Stripe Terminal: Stripe does offer card readers, starting at $59 for a countertop reader and $349 for a smart POS terminal. They work. But setup requires technical configuration, and the hardware selection is much smaller than Square's. For a business where the counter is the primary revenue channel, Stripe Terminal is not the natural choice.
Where Stripe has limitations:
- Not great for in-person-first businesses without a developer. The out-of-the-box experience is much thinner than Square's.
- Hardware selection is limited. Square has a full product line for every counter and table scenario; Stripe has a handful of readers.
- Customer-facing features like loyalty programs, appointment booking, and team scheduling require third-party integrations. Stripe does not provide them.
- The dashboard is clean but developer-oriented. A non-technical owner running a shop will find Square's dashboard more intuitive.
Fee note: Stripe's 2.9% + 30¢ online rate is identical to Square's. The real difference is what each platform does around the payment — not the payment itself. Choosing between them based purely on rates for standard transactions is the wrong frame.
Square — deep dive
Square gives you a free card reader on signup. That single fact captures the product philosophy: the lowest possible barrier to taking your first in-person payment. No developer, no configuration, no monthly fee to get started.
What makes Square genuinely powerful for retail and restaurant businesses is how much comes included at no extra cost on the base plan: inventory management, employee management, shift scheduling, and basic reporting. For a small shop or cafe, this replaces tools they would otherwise have to buy separately or manage in spreadsheets.
Vertical-specific editions: Square for Restaurants and Square for Retail are purpose-built and go meaningfully deeper than the base POS. Square for Restaurants handles table management, course firing, and kitchen display systems. Square for Retail handles variants, purchase orders, and vendor management. These are not thin add-ons — they are full POS products built for those industries.
Square Online lets you add an ecommerce storefront that connects to your POS inventory, so your in-person and online stock sync automatically. It is not Shopify, but for a business that wants a basic online presence without a separate platform, it works.
Square Appointments handles booking for service businesses — salons, spas, personal trainers. Square Loyalty and Square Marketing are paid add-ons that add customer retention tools on top of the payments layer.
Where Square has limitations:
- Subscription and recurring billing is available but less configurable than Stripe Billing. Complex billing scenarios (proration, trial periods, usage-based billing) are not Square's strength.
- Less developer-flexible. The API is solid, but Stripe's API is more powerful and better documented for custom integrations.
- International availability is limited. Square operates in the US, Canada, UK, Australia, Japan, and Ireland. Stripe supports 40+ countries.
- Square's ecosystem is built around Square. Moving off it later — switching POS, payment processor, and loyalty program simultaneously — involves real migration pain.
"Square gives you a functional retail or restaurant operation out of the box. Stripe gives you a payment infrastructure you can build anything on top of."
How we choose at Aplos AI
When working with small business clients, we look at one question first: is the revenue primarily online or in-person? The answer almost always settles it.
We recommend Stripe when: The business is primarily online, has a developer or uses a platform built on Stripe (Shopify, Squarespace, etc.), needs subscription billing, operates in multiple countries, or runs a marketplace or platform product.
We recommend Square when: The business is primarily in-person, does not have a developer, wants POS plus payments plus inventory plus staff management in one place, or is a restaurant, retail shop, or service business that wants vertical-specific software without stitching together multiple tools.
We flag the overlap when: A business does significant online and in-person volume. In that case, we look at total ecosystem switching costs and what they are already using before recommending a change. Migrating POS systems is painful. Migrating payment processors mid-growth is doubly so.
Five questions to make the decision
- Is your revenue primarily in-person or online? This is the single biggest determinant. If most transactions happen at a counter or table, start with Square. If most happen through a website or app, start with Stripe.
- Do you have a developer? If no, and your business is in-person, Square wins by default. Square's setup requires no technical knowledge. Stripe's full capabilities require someone who can work with an API.
- Do you need subscription or recurring billing? Stripe Billing is significantly more capable here. Trials, proration, dunning, usage-based billing — Stripe handles all of it cleanly. Square handles basic subscriptions but not complex billing scenarios.
- Do you need to accept payments internationally? Stripe supports 40+ countries. Square is limited to six. If you sell globally or plan to, this is not a close comparison.
- Do you want loyalty, scheduling, or marketing tools in the same ecosystem? Square has these built-in or as add-ons. Stripe does not. You would need third-party integrations to add them to Stripe.
The automation gap
Neither Stripe nor Square triggers post-payment automations natively. A customer pays. The transaction records. That is where both platforms stop.
No review request fires. No loyalty point gets assigned. No sequence starts if that customer goes 60 days without returning. No one follows up on the upsell that made sense given what they just bought.
Both platforms have webhooks — meaning a payment event can technically trigger an action in an external system. But actually building the connection (payment event fires, CRM gets tagged, review request sequence starts, loyalty credit applies) requires custom integration work. The webhook fires into the void unless something is listening on the other end and knows what to do with it.
This is the gap Aplos AI fills. We build the automation layer that sits on top of whichever payment processor you already use and makes it talk to your CRM, your email tool, and your review platform. You keep Stripe or Square. We add the follow-through that should be happening after every transaction but currently is not.
Every payment your business takes is a trigger point for a follow-up that probably is not happening automatically. We map the gaps in a free audit.
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