Square Payroll

2019 is starting out great for Square. If you think that Square is a payroll dongle company watch the video and imagine what financial service business they will disrupt next!


They are giving their customers everything they need and desire. Personally I think Dorsey is a creative genius but whatever. Planning to hold my shares for a long time. I like a CEO who will try anything.



I manage a number of (very) small companies and we have gone through a number of payroll services:

  • QuickBooks Online
  • QuickBooks Desktop
  • Square Payroll

All the services are priced somewhat similarly, with a monthly base price plus a per employee cost.
All the services purport to simplify the filing of federal and state paperwork which had to be done monthly, quarterly or annually.

Quickbooks Payroll online is integrated with the the Quickbooks online accounting package and does a good job of taking care of paying employees, entering hours, bonus, etc… and the filing of government forms is pretty easy, with online reminders and most forms able to be filed electronically.
The cost is about $35 + 3/employee

Quickbooks Desktop is by far the worst. Cost is roughly $40/mo + $3/mo/employee. There is a rebate on an annual basis.

It shows that the heritage is desktop based. The interface is pretty bad, you have to download constant updates, some things can be filed electronically, but some forms have to be filed via paper or go through a convoluted process.

I’m sure if I was steeped in the QB Payroll environment as a day job, it would become second nature, but to me it is just a big hassle and is what prompted the change to Square Payroll.

Square Payroll can be done either from the square website or from an App for phone or tablet. Interface is pretty easy. You can add/remove employees, it’s easy to track, and if you use the square POS for employee management and clock-in/clock-out, if can import those hours in the payroll app seamlessly, so you don’t have to enter the hours manually.

One interesting aspect is that when you get a new employee, you add them to the system and with their email address, they can self-enboard on the square system. So for direct deposits, SSN, address, etc… they fill it out directly and you don’t have to store it or even see any financial info.
The drawback is that they need to remember their logins to get their paystub and W-2 at the end of the year.
Cost is $28/mo + $5/employee that are active in a given month.
So if you have lots of part-time employees (like in retail) you don’t get charged if they don’t have any hours on a given month. Square also supports 1099 contractors at a flat $5/mo.

One significant difference between Quickbooks and Square is that Square takes ALL the tax liabilities are taken out of the bank account every pay period.
Employers have a portion of SS and Medicare they need to remit along with the tax witholding from your paycheck and a few other fees.
Most payroll package will wait until the payment to the IRS/Govt is due and then say “write this check” (usually the next month). Square takes the payment at the same time as the check is issued.

This is good & bad. Good in that you don’t have to “save” the money to pay the tax in 30 days, bad because it impacts your cash flow right now.

Verdict is still out, but definitely good points for ease of use.