About Square

Category: Payroll Services
Square Payroll software is a part of the Square family of products and is designed to help businesses make an easy job of paying workers and tax authorities. In this review, we’ll break down the services it provides to give managers a better idea if it’s what they could use.

Company: Square

Square Inc., is a San Francisco, California-based financial services and digital payments company. Its first platform was launched in 2010 by Jack Dorsey and Jim McKelvey. Since November 2015, it has been traded on the New York Stock Exchange under the ticker symbol SQ. Millions of companies use Square to take payments, manage staff, and conduct business in-store and online.

In-Depth Analysis

0 Overall
Price 4.5
Ease Of Use 4.0
Features 3.5
Support 4.0


  • Covers all payroll needs
  • Simple platform to use
  • Good integration with other Square apps


  • No site for HR ·
  • Direct deposit policy is four days
  • Some accounting apps don’t integrate

Square Comparisons

Plans & Pricing

There is a straightforward pricing system in place with the Square payroll offering. There are two different plans to choose from. The first of these is for both employees and contractors and it will cost $29 each month, as well as $5 per employee or contractor that gets paid in a given month.

The other plan will only be for 1099 contractors and it will cost just $5 each month and no monthly charge. This is a very good pricing plan and will be an ideal fit for a lot of smaller businesses. There is also a free trial period on offer, allowing you to explore these options without committing straight away.

Among the features that are offered as part of Square payroll included the filing of local, state, and federal taxes, as well as managing benefits, and full service for payroll needs. There is no annual contract that you need to commit to and there is even a feature for those hospitality companies that handle tips. This system sees the tracking and subsequent distribution of these tips.

Contractors only
up to 1,099 contractors, FREE Trial
Contractors & Employees
/mo +$5 /mo /employee
FREE Trial
Ease of Use

It can take some time for you to get fully set up with Square, particularly if there is a lot of prior data that has to be entered into the system. In terms of the navigation system, it is pretty much straightforward. Once you get up and running, you will be able to manage all relevant processes from the same dashboard.

However, there is still some work to be done to make the overall payroll offering to be as user-friendly as many of Square’s competitors. In terms of employee accounts, this side of the platform has been well done. It is simple for workers to create an account and manage their various types of payments.

Customer Support

There is a good level of quality replies when you pose a question or query to the Square support team. You can choose between live chat, email, and phone support. Most of these options will only be available during normal working hours. You will also get access to a somewhat limited collection of FAQs.

Phone Support
Phone Support
Available on weekdays on a toll-free number from 9am to 9pm CT
Live Online Chat
Live Online Chat
Available with extended response times
Available- response within 24-48 hours
Limited range of FAQs available
Features & Functionality
General Features

Automating key processes

One of the best features offered by Square’s payroll offering is the automatic calculating and filing of tax payments. This covers local, state, and federal taxes. You will also have your payroll processes automated in a similar fashion. This means that timesheets, salary info, overtime, etc. will be automatically taken into consideration.

There is the option for the payments to be sent via paper check or direct deposit. The administration of health and retirement benefits couldn’t be easier and there are now even capabilities to provide on-demand payment to workers.

Simply interface for workers

Contractors and employees can create their own accounts as part of Square payroll. This allows them to always be able to access their payroll info. This includes tax info, pay stubs, benefits, and so on. They can update different info, such as their tax withholdings and direct deposit accounts.

Management of benefits

Small businesses are able to choose and manage different types of benefits packages for their workers. This includes the likes of retirement benefits and health insurance. The employer is able to set the number of deductions for the paychecks to cover the various benefits for a given worker. Employees will use their personal payroll accounts to sign up for the benefits, meaning that there will be no paperwork on the business owner’s end.

Regular releases of new features

Square is known for being very innovative and it is regularly releasing new types of payroll features to make the user experience even better. Recent improvements include on-demand pay and instant payments. Over time, it is likely that more and more great features will be issued by Square.

  • 401(k) Tracking
  • Benefits Management
  • Check Printing
  • Direct Deposit
  • Multi-Country
  • Multi-State
  • Payroll Outsourcing
  • Payroll Reporting
  • Self Service Portal
  • Tax Compliance
  • Vacation/Leave Tracking
  • W-2/1099 Preparation
  • Wage Garnishment
Attendance Tracking
  • Calendar Management
  • Employee Scheduling
  • FMLA Tracking
  • Overtime Calculation
  • Reporting/Analytics
  • Self Service Portal
  • Time Tracking
Supported Devices
  • Windows
  • Android
  • iPhone/iPad
  • Mac
  • Web-based
Pricing Model
  • Monthly Payment
  • One-Time Payment
  • Annual Subscription

The Square payroll offering has a good range of features that covers all of the necessary functions that a small business needs to be taken care of. While it is still not the most user-friendly of platforms and it has a limited selection of integrations, these aspects are likely to improve over time. The pricing plans are very affordable and this is a no-brainer payroll solution if you already use other Square solutions.

Andrew O'Malley
Author: Andrew O'Malley
Andrew is a freelance writer who has been crafting valuable pieces of content relating to personal finance for more than five years. Previously, he studied Economics and Finance at university and he has professional qualifications relating to financial advice.

Square User Reviews

Veronica L
HR Director
Legal Services, 51-200 employees
Used for: 6-12 months
25 Jan - 2021

Simplicity at its finest!

Square Payroll quite literally takes most of the labor and difficulty out of running Payroll. If you are like me and work in administration or HR then this is the right software for you without the tedious entries and way more control of your payroll proc

Bill W
Financial Administrator
Government Administration, 11-50 employees
Used for: 1-2 years
15 Feb - 2021

It makes my job look too easy

Square payroll is an all-in-one payroll solution that's easy to use, so you don't have to worry about sending receipts, 1099 statements, quarterly reports, or new hire reports.


The one thing that I found problematic was that it is not easy to understand at first,and can be confusing to use at first

Lara B
11-50 employees
Used for: 6-12 months
13 Feb - 2021

Easy Payroll

Square made it easy for me to see how much I made and received my paycheck really quickly. It is equipped with great features and really am appreciating the simplicity of the software


It is alittle pricey for my liking

Tim W
Fishery, 11-50 employees
Used for: Less than 6 months
05 Apr - 2021

Easy enough

Covers all bases of the payroll aspect and does the job. We recently switched, so still need to get used to the software and if it can benefit us


-Easy to use.
- iOS & Android apps


Not so robust customer service. Better history options can be added

Barbara M
Airlines/Aviation, 1001+ employees
Used for: 1-2 years
05 Mar - 2021

Good Payroll

Overall, I enjoyed my use of Square but our company grew dramatically and it didn't fit our requirements anymore but overall a great product for beginners and getting started with handling your payroll processes