"Over 75% of Square Invoices get paid within a day."
0 Price
0 Ease Of Use
0 Features
0 Help And Support
Pros
  • Estimate and invoice management
  • Beginner-friendly UI
  • No recurring or upfront fee — pay per transaction only
  • Recurring invoices and automated payment reminders
Cons
  • No time tracking features
  • No late fee capabilities
Company Background

Square offers billing, invoicing, and Point-of-Sales tools to small businesses. Twitter founder Jack Dorsey and tech entrepreneur Jim McKelvey founded Square in 2009 as a Point-of-Sales software solution, but over time, it evolved to offer billing and payment management features.

Plans & Pricing

Square doesn’t charge any subscription or upfront fees. You only pay per transaction. Thus, you can sign up for Square and take your time without worrying about throwing money away.

That also means Square doesn’t have any formal “plans”. When you sign up for Square, you get all its basic billing and invoicing features.

Square Invoicing
2.9% + $0.30
per transaction

Square Invoicing

Square charges 2.9% + $0.30 per transaction on most transactions. You pay this every time your client pays you through their client portal.

Square’s invoicing fee is about on par with other big names, such as PayPal.

Square Invoicing + Card on File

When your customer doesn’t have a card present — usually meaning you have a customer’s stored card on file — Square increase the fee to 3.5% + $0.15 per transaction. This is because stored cards are slightly riskier, as neither your client nor their card need be present.

Thus, Square bumps up the fee to offset the risk.

That said, letting your customers save card info makes purchasing from you effortless. You’ll boost revenue and improve customer satisfaction.

This charge also occurs if you manually key in your customer’s card number. Again, this is slightly riskier than swiping or chipping the card.

Features & Functionality
General Features
Recurring Invoices

Many service businesses have retainer agreements with clients, meaning they get paid a fixed fee every month for an agreed-upon workload. Creating and sending retainer invoices every month is tedious, though.

Square lets you can store client credit or debit cards and set up recurring billing with ease. Square bills the card automatically, reducing work for both parties and increasing your chance of being paid on time.

Payment Reminders

Square also lets you set automated payment reminders to keep your clients in the loop about invoices or purchases coming up soon. You can schedule these ahead of time.

Deposits

Plenty of service businesses require clients to pay a deposit up front. This holds their spot in line and protects the company’s revenue in case of a dodgy client.

Square built in features that let you accept deposits and milestones, ensuring you get paid at the appropriate times for your hard work.

Estimates

Square has a host of estimate creation and management features. You can create and send multi-package estimates to give clients options depending on their budget and needs. You can then convert their chosen estimate into an invoice for easy money.

Square also provides numerous contract templates you can fill in and send with the invoice.

Features
  • Customizing your invoice
  • Tracking Invoice Views
  • Customizing invoice payment terms
  • Offer Discounts
  • Estimates
  • Recurring Invoices
  • Multi-Currency
  • Multi-Language
  • Client Portal
  • Send Emails
  • Automated Tax Circulations
  • Invoice Previews
  • Banking Data Synchronization
Payments
Features
  • Send receipts to customers
  • Online payments
  • Late Payment Fees
  • Track refunds and credits issues
  • Deposit Payments
  • Track Offline Payments
  • Credit Card Payments
  • Auto Payment
  • Payment reports
Time Tracking
Features
  • Automated bills for tracked hours per project
  • Different Rates for each Project
  • Generate Invoices
  • Timer
  • Tracking against clients and projects
Track Expenses
Features
  • Record Expenses
  • Record Mileage
  • Generate Invoices
  • Recurring Expenses
Supported Devices
Features
  • Windows
  • Android
  • Linux
  • iPhone/iPad
  • Mac
  • Web-Based
Pricing Model
Features
  • Monthly Payment
  • One-Time Payment
  • Annual Subscription
Ease of Use

Square has excellent, beginner-friendly UI and navigation. Plus, it’ll walk you through the software with a three-step onboarding sequence, helping you set up your account and familiarizing you with the basic features. It caps things off by guiding you through a mock invoice so you know how to perform the most important function included.

Customer Support

Square shines in customer service, offering everything from phone to live chat to blog posts and walkthroughs.

Like many companies today, though, Square constantly nudges users towards self-help resources like its forums and FAQs to minimize the need for support agents.

Phone Support
Phone Support
Available from 6AM to 6PM PCT on weekdays
Live Online Chat
Live Online Chat
You can find live chat support on the Square website
Email
Email
Email Square’s customer service from the customer support portal
Video Tutorials
Video Tutorials
Available on Square's support center and YouTube channel
FAQ
FAQ
Available for both prospective customers and current customers
Final Word

Square is a simple, budget-friendly way to streamline billing and invoicing. It skips fancy functions, instead of focusing on simple tools that automate and streamline your billing and invoicing processes. That said, Square offers other POS and eCommerce features in case you need them. Overall, Square is an excellent choice if you need a simple and efficient billing and invoicing management app.

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.