Square Review 2025

Category: Bookkeeping
Square is a suite of billing, invoicing, and Point-of-Sales tools serving small product-based and service businesses.
Company:Square

Square Bookkeeping Plans & Pricing

Full-service payroll
$35
/mo
+$6 Monthly fee per person
Contractor-only payroll
$6
/mo
Per person paid

Square Comparison

Expert Review

4.3
Price
5.0
Ease Of Use
4.5
Features
3.5
Support
4.0

Pros

v-pro
Robust estimate and invoice management
v-pro
Recurring invoices and automated payment reminders
v-pro
Simple UI
v-pro
Competitive transaction fees

Cons

x-con
No time tracking
x-con
Can’t charge late fees
x-con
Can’t add expenses to invoices

Square Bookkeeping's Offerings

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.

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.

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.

x-con
General Ledger
v-pro
Manages Accounts Payable/Receivable
v-pro
Income & Expenses Tracking/Management
v-pro
Account Reconciliations
v-pro
Bookkeeping Services Integration
v-pro
Financial Reporting
x-con
Receipt Scanning
v-pro
Invoicing
v-pro
Dashboards
x-con
Auditing
x-con
Inventory Tracking/Management
x-con
Pay Bills
x-con
Cloud-based
x-con
Collections
x-con
Multi-currency
x-con
Multi-user Access
v-pro
Manage Vendors/Contacts
x-con
Manage Purchase Orders
x-con
Bank and Credit Card Synchronization
v-pro
Payroll Management
v-pro
Convert Quotes to Invoices
v-pro
Mobile App

Tax Preparation

Simplify and optimize tax filing with expert features and tools.

v-pro
Tax Compliance
v-pro
Manage Tax Calculations/Reporting
v-pro
Accountant-prep Friendly/Accessible

Time-Saving Automations

Automate repetitive tasks to improve efficiency and productivity.

v-pro
Automation of Invoices/Notifications
x-con
Suggests Transaction Matches
x-con
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.

v-pro
Payment Processing
v-pro
Payroll Processing
x-con
Project Management
v-pro
Time tracking
v-pro
Third-party Integrations

Supported Devices

Access and use on a variety of compatible devices.

x-con
Windows
v-pro
Android
x-con
Linux
v-pro
iPhone/iPad
x-con
Mac
v-pro
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.

Verdict:

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.

User Review

4.5
5
1 Users
(1)
4
1 Users
(1)
3
0 Users
(0)
2
0 Users
(0)
1
0 Users
(0)
Write a review
Leave a review, help others get it right the first time.
logoWrite a Review
2 Reviews
1-10 employees
Used for: Less than 6 months
14 Jul - 2021
Very convenient
It is a pleasure to work with Square. It offers the ability to manage sales, inventory, gift cards, rewards, and you can process any payment on the go.
Dislike:
  • The percentage that goes back to Square is rather high
11-50 employees
Used for: 2+ years
12 Jul - 2021
Helpful
I have been using Square to process my credit card sales for years, and I have never encountered any problems. It's been nothing but helpful since the beginning.
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