Square Payroll Review - The Good and Bad for 2022


Square Payroll is a full-service solution to help you pay your employees on time, offer them benefits, and automatically file taxes all in one place. With instant payments, seamless time tracking, and feature-rich solutions for teams, Square Payroll can help you streamline your entire payroll while complying with all relevant laws. 

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Square Payroll Compared to the Best Payroll Services

Compared to other payroll services on the market today, Square Payroll is an excellent all-in-one service. After reviewing dozens of options for our list of the best online payroll services, we found a few Golden Eggs, including the following: 

Rippling is our number one recommendation for most people because of its expansive list of integrations and excellent automation process. Rippling is a scalable payroll service that offers valuable HR management tools that help streamline all payroll needs. Sign up to see a free demo today.

Gusto is another excellent payroll service for its intuitive user interface, automatic pay runs, and seamless onboarding features. You can sign up to Gusto today with no long-term commitment.

QuickBooks offers an affordable payroll solution for accounting processes, with real-time syncing and industry-leading direct deposit speeds. With a pick-and-choose pricing model, you won’t ever have to pay for features you won’t use, making QuickBooks even more affordable. See if QuickBooks is right for you with a 30-day free trial.

Square Payroll: The Good and The Bad

Just like for all payroll services, there will be good and bad features to consider. After extensive research, we found that Square Payroll offers excellent features that most users are happy to continue using, with only a few drawbacks. Let’s take a deep dive into both sides of the spectrum before you decide.

What Square Payroll Is Good At

Square Payroll offers an all-in-one payroll service with employee benefits, automatic tax filings, and instant payments, so you don’t have to worry about the nitty-gritty while managing your employees’ pay. As a feature-rich software for teams, you will find that Square Payroll is easy to use and offers seamless time tracking, team scheduling, and expert support for all your account setup needs.

Employee Benefits: Square Payroll makes it easy to offer benefits to your team with little to no effort. From workers’ comp and health insurance to 401(k) retirement plans, Square Payroll will help you set up the benefits by calculating deductions and contributions for each pay run. You can choose from the top workers’ comp and health insurance carriers with no hidden fees. 

Square Payroll lets you customize your benefits package to suit your employees better and fit your budget. All you do is choose your benefits during setup, which takes a few minutes, and then invite your team to enjoy their benefits.  

Automatic Tax Filings: Square Payroll lets you focus on your business by filing your state, federal, and local payroll taxes automatically. Every time you run your payroll through Square Payroll, it calculates, withholds, and sends the right amount of taxes to your respective agencies. You can also run payroll across multiple states and file quarterly or yearly. 

Square Payroll also offers ongoing compliance with ever-changing tax laws and will automatically update your payroll if there are any changes at any point. Square Payroll doesn’t forget about important forms, as it has an internal revenue service for forms 940, 941, 944, and 1099-NEC—as well as social security administration for W-2 and W-3 forms.  

Instant Payments: You can connect your payroll to your Square checking account or balance to pay your employees instantly. With Square Payroll, there’s no need to submit your payroll up to four days in advance—instead, you can utilize Square’s checking account and use funds from your balance to pay your team faster. You can also hold your funds for as long as you need and run your payroll one day before your usual payday. 

Your team can expect to receive their payments the next day if you run your payroll through direct deposit. However, they will get paid instantly if they use Cash App, even on weekends.

Seamless Time Tracking: You can easily track your employees’ hours with Square Payroll’s software that syncs directly to your timecards and point of sale. When your employee checks in and signs out, Square Payroll automatically calculates overtime pay and double-time pay based on the rules you set in the Square dashboard. Square’s time tracking feature also tracks unpaid breaks, and you can save money on labor costs and prevent employees from clocking in early or for unscheduled shifts by reporting scheduled vs. actual hours worked. 

Team Scheduling: If you need to find scheduling software that works for everyone, Square Payroll’s team scheduling feature might be the perfect solution for you. You can create and publish shifts in just a few clicks and assign work schedules via the mobile app or email. You can also copy previous shift schedules, so you don’t have to waste time and start from scratch each week. 

A new tool in Square Payroll’s scheduling feature includes being able to accommodate last-minute changes, meaning your team can pick up shits, swap them, or request time off with approval. 

Expert Support: Square Payroll offers a variety of support options, including expert support with payroll specialists to help you set up your account and start paying your team immediately. Square Payroll has a phone and email support channel and live chat support from US-based onboarding specialists from Monday to Friday, 6am-6pm. Aside from live support, Square Payroll also has a support center, business resource center, and a community forum where you can receive additional support from Square users.

What Square Payroll Is Lacking

While Square Payroll exceeds in the general payroll services area and offers rich features for teams, it also lacks in some areas. We found that Square Payroll does not offer customization on many aspects of its software. According to a few reviews, users have experienced time-consuming software glitches and slow customer support.

No Customization: After looking through dozens of reviews, the most recurring negative review involved Square Payroll’s customization or lack thereof. According to a few users, you can’t customize many aspects of the software, including changing or canceling your payroll at a later date, not being able to change the cut-off times for payroll, not being able to sort through pay history, or editing timecards. Using inflexible software can be inconvenient, especially if you have a big team and many people to pay for.

Software Glitches: A few users claimed that Square Payroll had a few glitches that users couldn’t fix for a long time. One user said that whenever their employees would punch in their hours, the software would freeze, and they couldn’t fix it without calling customer support, which was a waste of time. Another user said that during a device update, Square Payroll crashed for a week for no reason, leaving this particular user to outsource an entirely new software for payroll. 

Slow Customer Support: Despite Square Payroll offering expansive support options, a few users have complained about its customer support, saying it’s very slow and not entirely helpful. One user claimed that it took up to a week to hear back from anyone via email and live chat support was confusing and kept disconnecting. Another user said that while the support was helpful, it took too long, and the user had already figured out the issue before hearing back from a representative. 

Square Payroll Options and Pricing

Square Payroll offers a wide range of products in commerce, banking, team software, and development. But Square Payroll offers two main additional products that integrate into its payroll services, which include the following:

Square Messages

Seamlessly connect with customers through Square’s messaging system. With one way to manage all of your conversations, you can transform your communication line without outsourcing a whole new system.

Screenshot showing how you can use Square’s messaging system on desktop and mobile. 

Square’s messaging system is the only solution your business needs to reach out to customers easily, respond instantly, and transact directly. You don’t have to rely on phone calls, as Square Messages lets you create a single channel for texting and emailing without using your personal number or email address. 

The messaging system is completely flexible and already integrated into the rest of Square’s software. For example, you can sync your messages with Square’s appointments feature to stay on schedule, never miss a booking, and build trust with your clients. 

Square also lets you offer coupon codes and send online payment links to ensure you never miss a sale again. You can accept multiple payments from multiple channels, and with zero monthly fees, you only pay when you make a sale. 

Instead of catching up on customer emails, you can respond to your customers in real time with Square’s simple notification system. You can also respond to feedback easier and have the option to offer a special deal to unsatisfied customers. Square is also working on a beta version of a messaging system that allows you to send and receive photos via direct message.

The best part about this messaging system is Square Assistant, which is an AI-powered tool to help answer questions for you, so you don’t have to run your business from the sidelines. Square Assistant can help you respond to customers, schedule, reschedule and cancel appointments, and automatically update your calendars. 

Square Messaging is free for all existing Square Payroll members on the Employees and Contractors plan, which is currently $40 per month. 

Square Banking

If you want to streamline your cash flow and transform your banking, Square Banking is the perfect solution for you. With zero monthly account fees and a simple interface, you can sell, save, spend, and borrow as fast as you want.

Screenshot showing how Square Banking makes it easy to view your savings. 

With zero overdraft, opening deposit, minimum balance, and monthly account fees, you can open a savings and checking account with ease. You can also become eligible for a Square loan and repay it through your sales, all in one intuitive application. 

You can access your sales instantly through Square’s FDIC-insured checking account. If you pair your checking account with a Square debit card, you can spend your funds immediately without waiting. 

If you are focused on saving your funds, Square offers a savings account that lets you earn 1% APY with no minimums or monthly fees. Square also lets you set up an automated savings process, where you can decide how much money you want to save with each transaction. 

All Square bank accounts are FDIC insured for up to $250,000. You also get free transfers between accounts, and you can view all your sales and savings in the Square dashboard.

And don’t forget about Square’s loan system. If you need money to keep your business moving forward, you can apply for a small business loan for between $300-$250,000. 

You can get a customized offer based on your sales and then choose your loan size to make it easier for you to repay the loan with a percentage of your sales. There is also no ongoing interest, just a simple flat fee. 

Similar to Square’s messaging product, you can only use Square Banking as an existing member, which is also $40 per month. 

Square Payroll in Summary

Overall, Square Payroll is an excellent payroll service because of its seamless tools, such as instant payments and automatic tax filings. Its downfalls aren’t severe but are still aspects you should consider before investing in software. 

However, Square Payroll isn’t the only payroll service with seamless solutions. We think Rippling is an excellent option for its automation processes. Gusto is great for its intuitive interface and powerful onboarding features. And if you are looking for a payroll service that offers inclusive accounting solutions, QuickBooks is the best service on the market. 

Want to read more about the best payroll services? We reviewed dozens of options and narrowed it down to the top seven. If you want to scope out all of your options, see all of our top picks here



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