
Choosing between Simple Invoices and Square Invoices hinges on business size, payment processing needs and budget. Both provide strong invoicing features but serve distinct user priorities and operational demands.
Simple Invoices offers a pricing structure of $15/month or $149/year with a 14-day trial and unlimited users, making it suitable for teams. In contrast, Square Invoices provides a free plan alongside paid tiers of Plus at $49/month and Premium at $149/month which can be costlier for businesses needing advanced features.
Invoicing features like custom templates and recurring billing are available with both Square Invoices and Simple Invoices. However, Simple Invoices lacks automated payment reminders whereas Square does, improving cash flow management. Furthermore, Simple Invoices completely lacks the ability to track expenses while Square only offers a restricted version. Time and mileage tracking are not supported by either platform which could be problematic for service-oriented companies that require precise time management.
Credit cards, Apple Pay, Google Pay, Cash App Pay, ACH transfers and Afterpay are just a few of the payment gateway methods that Square Invoices accepts which improves collection rates. Simple Invoices only accepts payments via credit cards and PayPal with higher processing costs for PayPal. Both platforms work with popular accounting programs like Xero and QuickBooks but Square uses its own Customer Directory system while Simple Invoices offers more options for CRM integration.
Square Invoices is appropriate for companies handling sensitive data because it is more secure than Simple Invoices because of its data encryption, GDPR compliance and automatic backups. Simple Invoices excels in multi-currency support and localization across seven languages, making it superior for global businesses even though it only offers manual backups and lacks data encryption and GDPR features.
While Simple Invoices relies on community forums and documentation which may not be able to satisfy users’ urgent needs, Square Invoices provides comprehensive support via phone, chat and email, available around-the-clock for Premium plan users.
For foreign independent contractors or small companies in need of community support, unlimited team members and multi-currency support, go with Simple Invoices. For flexible payment options, strong security, GDPR compliance, automated payment reminders and courteous customer service choose Square Invoices. Solopreneurs on a tight budget can profit from Square’s free plan while expanding companies should compare the $15/month cost of Simple Invoices with Square’s Premium plan for more sophisticated features.
| Simple Invoices | Square Invoices | |
|---|---|---|
| Core Features | ||
| Custom Templates | Yes | Yes |
| Send Estimates / Quotations | Information not available | Yes |
| Recurring Billing Automation | Yes | Yes |
| Expense Tracking | No | Limited |
| Time Tracking | No | No |
| Mileage Tracking | No | No |
| Automated Payment Reminders | No | Yes |
| Project-Based Billing | Yes | Yes |
| Tax Handling | Yes | Yes |
| User Permissions / Role Management | Yes | Yes |
| File Uploads | Yes | Yes |
| Pricing and Plans | ||
| Free Plan Availability | Yes | Yes |
| Pricing Range | Monthly: $15/month Annual: $149/year |
Free: $0/month Plus: $49/month Premium: $149/month |
| Trial Period | 14 days | No |
| User Limits | Unlimited users (hosted) | No strict limits |
| Client Limits | Unlimited clients | Unlimited clients |
| Storage Limits | Information not available | Unlimited cloud storage |
| Payment Processing Fees | Stripe: 2.9% + $0.30 PayPal: 3.49% + $0.49 |
Varies by payment method |
| Ease of Use | ||
| User Interface | Simple | Simple |
| Onboarding Experience | User guides & forums | Yes |
| Mobile App Availability | iOS and Android | Yes |
| Mobile App Functionality | Invoices, estimates, expenses | Full invoicing & payments |
| Integration | ||
| Payment Gateways Supported | Credit Cards, PayPal | Cards, Apple Pay, Google Pay, ACH |
| Accounting Software Compatibility | QuickBooks, Xero, FreshBooks | QuickBooks Online, Xero |
| CRM Integration | HoneyBook, Pipedrive, Salesforce | Built-in customer directory |
| API Availability | Limited (via alternatives) | Yes |
| Reporting & Analytics | ||
| Bank Connections | No | Yes |
| Pre-Built Financial Reports | Yes | Yes |
| Custom Report Creation | Yes | Yes |
| Security & Compliance | ||
| Dashboard Metrics | Yes | Yes |
| Data Encryption | No | Yes |
| GDPR Compliance | No | Yes |
| Backup Options | Manual | Automatic |
| Customer Support | ||
| Support Channels | Community forums, docs | Phone, Chat, Email |
| Help Center / Knowledge Base | Yes | Yes |
| 24/7 Support | No | Partial |
| Adaptability | ||
| Multi-Currency Support | Yes | No |
| Localization | Multiple languages | English |
| Industry-Specific Customization | No | Yes |
| Scalability | Freelancers & small businesses | Freelancers to SMBs |
| Read Simple Invoices Review | Read Square Invoices Review |