"Square is an excellent billing solution, offering a budget-friendly way to streamline your invoices and ensure you get paid on time."
0 Price
0 Ease Of Use
0 Features
0 Help And Support
Pros
  • Robust estimate and invoice management
  • Recurring invoices and automated payment reminders
  • Simple UI
  • Competitive transaction fees
Cons
  • No time tracking
  • Can’t charge late fees
  • Can’t add expenses to invoices
Company Background

Square is a suite of billing, invoicing, and Point-of-Sales tools serving small product-based and service businesses. It was founded by Twitter founder Jack Dorsey and tech entrepreneur Jim McKelvey in 2009 as a Point-of-Sales software solution but has since evolved to encompass many other billing and payment management features.

Plans & Pricing

Square is free in terms of upfront or recurring fees. Instead, you only pay per transaction. This makes it easy to sign up for Square on your own schedule without worrying about wasting money.

With that said, they charge two different transaction fees depending on how the customer pays.

Square Invoicing
2.9%+$0.30
per transaction
No monthly fee
Square Invoicing + Card on File
3.5%+$0.15
per transaction
No monthly fee

Square Invoicing

Square’s regular invoicing fee is 2.9% + $0.30 per transaction — you pay this when your client pays you via their client portal. This is comparable with many other free solutions like PayPal invoicing. You have access to all Square Invoicing features under this “plan”.

Square Invoicing + Card on File

Square bumps the fee up a bit to 3.5% + $0.15 per transaction for “card-not-present” payments, which most often occurs when a client uses a stored card to pay an invoice. Stored cards are slightly riskier — as neither your client nor their card need be present. This somewhat higher fee helps Square cover this risk. Still, allowing your customers to save cards makes purchasing from you effortless, so you’re also likely to earn more revenue to cover the fees. Note that this charge also occurs if you manually key in your customer’s card number.

Features & Functionality
General Features
Recurring Invoices

Service businesses are often on retained for some of their clients. Sending your retainer clients invoices every month can be a headache, which is only made worse when they seem to dodge around paying you.

However, thanks to Square, you can store client credit or debit cards and set up recurring billing quite easily. Their card will be charged automatically, so they won’t have to remember to pay, and you won’t have to stress about non-payment.

Payment Reminders

Another automation feature Square offers is payment reminders. When creating your invoice, you can schedule payment reminders ahead of time to increase your clients’ chances of paying on time.

Deposits

If you run a service business, you likely require your clients to put down a deposit upfront to reserve a spot in your calendar or protect yourself if they’re a bad client.

Square lets you set up deposits and other milestones, so you can get paid when you complete essential portions of each client project.

Estimate Management

Square provides excellent estimate creation and management features. You can create and send custom, multi-package estimates so that clients can pick the best one based on their needs and budget. Once they choose their package, you can convert the estimate into an invoice with a few clicks.

To streamline documents even further, Square offers numerous contract templates you can fill in and send with the invoice.

Features
  • General Ledger
  • Bookkeeping
  • Manages Accounts Payable/Receivable
  • Income & Expenses Tracking/Management
  • Account Reconciliations
  • Financial Reporting
  • Receipt Scanning
  • Invoicing
Track Expenses
Features
  • Record Expenses
  • Record Mileage
  • Generate Invoices
  • Recurring Expenses
Tax Preparation
Features
  • Tax Compliance
  • Manage Tax Calculations/Reporting
  • Accountant-Prep Friendly
Time-Saving Automations
Features
  • Automation of Invoices/Notifications
  • Suggests Transaction Matches
  • Purchase Order Automation
Add-Ons

Square offers numerous other small business management beyond their invoicing. Some are free, while others cost money.

Additionally, Square integrates with several administrative and marketing tools to streamline your operations, such as Acuity scheduling software, ActiveCampaign, JotForm, Mailchimp, and TSheets.

Features
  • Payment Processing
  • Payroll Processing
  • Project Management
  • Time Tracking
  • Third-Party Integrations
Supported Devices
Features
  • Windows
  • Android
  • Linux
  • iPhone/iPad
  • Mac
  • Web-Based
Ease of Use

Square’s UI is excellent and easy for beginners to learn. It walks you through the product with a three-step onboarding sequence to get your business set up and explain some basics. It’ll even let you send yourself a mock invoice to ensure everything works how you want it to.

Customer Support

Square provides its customers with nearly every common support option, from phone to live chat to tutorials and blog posts. Customer support is generally pretty strong, too.

That said, the company nudges users towards the Square community, FAQs, and other resources to minimize the need for support agents.

Additional customer support:
Social Media
Square support will respond on social media channels such as Twitter.

Community
Join Square’s seller community to talk about Square and business with other users.

Blog
Square’s blog has more articles about software and small business in general.

Phone Support
Phone Support
Access phone support Monday-Friday from 6 am to 6 pm
Live Online Chat
Live Online Chat
You can ask for help via live chat
Email
Email
Email the Square customer service from the support portal
Video Tutorials
Video Tutorials
Available in the Square support center as well as YouTube
FAQ
FAQ
Simple presale FAQs, guides, and other resources available
Final Word

Square is an excellent billing solution, offering a budget-friendly way to streamline your invoices and ensure you get paid on time. Rather than focus on fancy features, it hones in on automating your invoicing and payment reminders — and does them well. And if you want to add more tools to your business, Square has other PoS and e-commerce features. Square won’t do your bookkeeping for you, but fortunately, you can integrate it with other products to cover those areas. So if you need a way to manage your billing more efficiently, consider Square.

Bradley Schnitzer
Author: Bradley Schnitzer
Bradley Schnitzer helps businesses gain loyal customers through informative content pieces and persuasive copy. He is passionate about personal finance and helping budding freelancers further their careers.