InvoiceQuickly vs Square Invoices — Which Invoicing Tool Fits Your Business?
Square Invoices is a free invoicing feature built into the Square payments ecosystem, ideal for businesses already accepting Square payments. InvoiceQuickly combines AI-powered outgoing invoicing (5 invoices & 5 clients on the free plan after signup; unlimited on paid from $9/mo) with Autopilot for incoming invoice automation — AI OCR extraction, PO matching, approval workflows, and ERP sync. This comparison helps you decide which tool is right for your invoicing needs.
Last updated: May 2026
Pricing Comparison
Free to start — 5 invoices included. Autopilot (AP automation) starts at $29/month.
Free to send invoices. Payment processing: 2.9% + $0.30 (online), 3.5% + $0.15 (keyed-in). Square Invoices Plus $20/month.
Invoice Creation
| Feature | InvoiceQuickly | Square Invoices |
|---|---|---|
| AI-generated invoices from text | Yes — describe work, get PDF | No |
| Invoice templates | 200+ industry & country templates | Basic customizable template |
| Multi-currency invoicing | 25+ currencies | Limited (primary currency only) |
| Recurring invoices | Coming soon | Yes |
| Estimates & deposits | Coming soon | Yes — with deposit requests |
Payments & Tracking
| Feature | InvoiceQuickly | Square Invoices |
|---|---|---|
| Payment tracking | Yes — free | Yes — within Square dashboard |
| Online payments | Coming soon (Stripe/PayPal) | Yes — card, ACH, Cash App, Apple Pay |
| Payment processing fees | None | 2.9% + $0.30 per online payment |
| Late payment reminders | AI-drafted emails (free) | Automated reminders (Plus plan) |
Accounting
| Feature | InvoiceQuickly | Square Invoices |
|---|---|---|
| Expense tracking | Not included (invoicing focus) | Basic (via Square Dashboard) |
| POS integration | Not included | Deep Square POS integration |
| Tax compliance templates | 200+ country templates with local tax fields | US-focused |
AP Automation (Incoming Invoices)
| Feature | InvoiceQuickly | Square Invoices |
|---|---|---|
| AI OCR data extraction | Yes — PDFs, images, scans, any language | No |
| Duplicate detection | Automatic with anomaly flagging | No |
| PO matching | 2-way and 3-way (Business+) | No |
| Approval workflows | Configurable multi-level (Business+) | No |
| ERP/accounting push | QuickBooks, Xero, Sage, SAP, API/webhook | No |
Pricing & Limits
| Feature | InvoiceQuickly | Square Invoices |
|---|---|---|
| Free plan | Yes — 5 free invoices, 5 clients. Upgrade for unlimited. | Yes — free to send (fees on payment receipt) |
| Branding | Full customization (logo, colors, layout) | Limited — Square branding present |
| Users | 1 user on free plan, unlimited on paid | 1 (free), unlimited (Plus $20/mo) |
Pros & Cons
InvoiceQuickly strengths
- AI generates invoices in seconds from plain-text descriptions
- 200+ templates for global tax compliance — not limited to US
- No payment processing fees eating into your revenue
- Advanced AP automation for incoming invoices (Autopilot)
- Full brand customization without third-party branding
Square Invoices strengths
- Built-in payment processing with card, ACH, Cash App, and Apple Pay
- Deep POS integration for retail and restaurant businesses
- Estimates and deposit requests built in
- Part of the broader Square ecosystem (payroll, banking, appointments)
Who should pick which?
Pick InvoiceQuickly when…
Pick InvoiceQuickly if you're not also running Square POS or Square's appointment system. Square Invoices is excellent inside the Square ecosystem (sync with POS sales, Square Customer Directory, payment-on-arrival workflows) but bare outside it. InvoiceQuickly's AI generation, 200+ templates, and Autopilot AP automation give you a fuller invoicing platform without the Square hardware/POS coupling.
Pick Square Invoices when…
Pick Square Invoices if you already use Square for in-person payments — restaurants, salons, retail, mobile services. Square Invoices integrates natively with your sales history, customer records, and payment methods you've already configured. The 2.9% + 30¢ online card fee mirrors what you're already paying for in-person card sales.
Three worked scenarios
Real situations and the recommendation we'd actually give.
Mostly accepts payment at job site via Square reader; occasionally invoices for fleet accounts.
→ Square Invoices — keep in-person and invoicing in one ecosystem.
Sends 2-3 invoices per booking; needs branded templates.
→ InvoiceQuickly — photography-specific template, deposit tracking, professional brand presentation. Square's invoice template is utilitarian.
POS in Square, catering invoices needed monthly.
→ Square Invoices for catering inside the same ecosystem; InvoiceQuickly only if catering grows enough to warrant separate workflows.
Switching from Square Invoices
Square exports invoices and customer records as CSV. The sticky migration cost is payment processing — if you've already onboarded clients to Square's payment links, switching them to a new processor adds friction. Most service businesses run both systems for a quarter, sending new invoices via InvoiceQuickly while completing in-flight Square invoices.
The Verdict
Choose InvoiceQuickly if you want AI-powered invoicing with a free tier (5 invoices, 5 clients), professional templates, global multi-currency support, and no platform transaction fees on invoice creation. Choose Square Invoices if you're already in the Square ecosystem and need seamless payment collection with POS integration, especially for US-based retail or service businesses.
Last verified: April 2026
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Get Started FreeFrequently Asked Questions
Is Square Invoices really free?
Square Invoices is free to create and send, but Square charges 2.9% + $0.30 on every online payment and 3.5% + $0.15 for manually keyed transactions. On a $3,000 invoice, that's roughly $87–$105 in fees. InvoiceQuickly includes up to 5 invoices on the free plan with no subscription fee; unlimited invoicing is available on paid plans.
Can I use Square Invoices internationally?
Square operates in the US, Canada, UK, Australia, Japan, and a few other countries, but invoicing is USD-focused with limited multi-currency support. InvoiceQuickly supports 25+ currencies and 200+ templates for international tax compliance.
Does Square Invoices have AI features?
No. Square Invoices uses traditional form-based invoice creation. InvoiceQuickly's AI generates complete invoices from plain-text descriptions in about 5 seconds.
Can I use InvoiceQuickly and Square together?
Yes. Create professional invoices in InvoiceQuickly with your preferred template, then include your Square payment link in the invoice for clients who want to pay via card or Cash App.
What is InvoiceQuickly Autopilot?
Autopilot is the paid tier that automates incoming invoice processing — forward vendor invoices via email, Gmail/Outlook connection, or upload, and AI extracts data, validates it, detects duplicates, and pushes it to your accounting system. Autopilot is included on the Business plan ($29/month).
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