Live Q&A: Ask us anything about Square Payroll

On Tuesday, December 4th at 11am PST, we will host a Live Q&A about Square Payroll. If you’ve been thinking about switching payroll providers, or you’re just curious to learn more about Square’s full-service payroll product, you should check this out. The best time of year for changes in how you run payroll is now! This is because you can start fresh with a new provider at the beginning of 2019, simplifying your setup and tax filing process.


In this Q&A we’ll explain how our product works and introduce our newest features, including benefits like health insurance and retirement savings for your and your team, automatic tip splitting, integrated timecard importing, employer and employee mobile apps, and our nationwide availability. We’ll have Square Payroll General Manager, Caroline Hollis, here to answer all your questions and help you get the most out of Square Payroll for your business.


@caroline has been part of the Square Payroll team since its inception in 2014. In her time on the Payroll team she has been an integral part in building the product from the ground up. She understands that Payroll is critical for both small business owners and their employees. For employers, payroll is often the business’ largest recurring expense. For employees, a paycheck makes up most or all of their income.

- .gif


A few example questions:

  • What does ‘full-service’ payroll mean, and what is included with my subscription?
  • Do you really do all my payroll tax calculations and filings?
  • What are my benefits options with Square Payroll?
  • How does payroll work with the rest of my Square account?
  • What can my employees do with the Square Team App?
  • Can I run payroll from the Square Payroll mobile app?
  • Why did Square build a payroll product?
Message 1 of 93
1 Best Answer

Accepted Solutions
caroline Square

Re: Live Q&A: Ask us anything about Square Payroll

Best Answer

Thanks to everyone for the great questions today! We built Square Payroll because we wanted to make payroll so simple it could become invisible. You’ve raised great suggestions about how we can improve the product that we’ll be sharing with the team and addressing in 2019. Your requests are what drive what we build, so please keep sending us your thoughts!


Here’s my summary of a few themes I saw in today’s questions:

  • You are busy! There are many factors that go into managing payroll, and anything we can do to help you save time is a huge win.  By making it easier for you to track employees’ time, import and pay out credit card tips, deal with cash tips, or calculate and import commissions, we let you focus on other parts of your business. Our automatic payroll feature works great for people who want to set and forget payroll. Our Payroll app enables you to manage payroll on the go. And we handle all your tax calculations, payments and filings so you don’t need to worry about the details.
  • Every business is different, so flexibility matters. From ownership structures to pay cadences to how tight you are on your cash flow each month, we strive to build a payroll product that works for your needs. We’ve made a lot of progress, but there’s more we can do to make it easier to customize how you track and distribute tips and continue automating these steps for you. Thank you for sharing your ideas on how we can improve.
  • Benefits are important to you and your employees. We were thrilled to launch our suite of benefits products last month which includes health insurance, retirement savings plans, pre-tax benefits and pay-as-you-go workers’ comp. Many of you are already taking advantage of this, and hopefully our answers below about who is eligible, how to sign-up, whether you can offer benefits to part-time employees (you can!), and more are helpful as you evaluate different options. See here for more details on our benefits offering.
  • We’re here to help you. We know payroll is tricky. So whether you’re getting setup with a payroll provider for the first time, switching from another provider, or already using Square Payroll and you have some questions, our US-based team is here to help you. New customers can reach out to our sales team, and existing customers can contact our CS team with your customer code!

Again, thanks for your participation today. Remember that if you want to make the switch to Square Payroll, this is a great time of year to do it. And if you already use Square Payroll, tell your friends - they get their first month free and you get a $100 Amazon.com gift card when they sign up using your referral link [valid at time of publishing, but subject to change without notice]. Just visit the ‘Earn Rewards’ tab in your Payroll Dashboard to see your code.

Message 92 of 93
Pesso Super Seller

Re: Live Q&A: Ask us anything about Square Payroll

Thanks so much @caroline for hopping on here to do the Q&A! So cool!


We’re looking at finally making the jump to Square Payroll this year with all the awesome new features unveiled!


A few questions:

Does tip splitting work across shifts or only across the entire pay period? I have busy shifts where a lot of tips come in and non busy shifts where very few tips come in, and I would prefer my tips to split by shift or by hour rather than by total hours worked across all shifts in the pay period. 


I use homebase to track hours because of the scheduling system - how does creating/importing/editing employees work across these services, especially when my existing employees already have Homebase accounts that they log into?

How does editing & fixing clock in and out times work across these two? Especially with automatic imports to Square Payroll. 




Message 2 of 93

Re: Live Q&A: Ask us anything about Square Payroll

I also would like to know when Square Payroll will account for the amount of time that an employee works and the tips that were earned during this time.  We are not concerned about cash tips, but I have a very busy morning shift that receives a lot more tips than the afternoon.  We really need to account for the tips during the time that the employee worked, not an even split across all hours for the employees that worked during that day.

Message 3 of 93
caroline Square

Re: Live Q&A: Ask us anything about Square Payroll

Hi @TorpedoCoffeeThanks for the feedback. Similar to what we told @Pesso up above, you can currently pool and split tips across the entire pay period or pay the tips directly to the employee who collected the tips. We are looking to build out additional tip splitting options and splitting tips across shifts is one of our top requests as you can see from the multiple comments in this Q&A. We will let you know as soon as this feature is available!

Message 4 of 93

Re: Live Q&A: Ask us anything about Square Payroll

If I want to sign up to offer benefits in my company, can the employee use that offering as a life event to leave the benefits at another job?

Message 5 of 93

Re: Live Q&A: Ask us anything about Square Payroll

How many employees do you have to have to offer employee benefits? 

Message 6 of 93
caroline Square

Re: Live Q&A: Ask us anything about Square Payroll

Great questions on benefits, @qrobertson!


To offer health benefits to your business, there need to be at least 2 people in the company, and at least one person must be a W-2 employee. You can start group insurance as long as you meet eligibility even if not all your employees need insurance. There are some restrictions if the only two people in the group are husband and wife.


If your employees receive coverage through another job or through the individual market, they can switch to your group health plan. No qualifying life event is needed to make this switch. They will have approximately 1-2 weeks to switch onto your plan from the time they become eligible to enroll.


If you have a unique circumstance, don’t hesitate to reach out to our health insurance partner, SimplyInsured at squaresupport@simplyinsured.com.


In addition to health insurance, you can also sign up for 401(k), pre-tax benefits and workers’ compensation through the Square Payroll dashboard.

Message 7 of 93
caroline Square

Re: Live Q&A: Ask us anything about Square Payroll

Hi @Pesso!

With Square Payroll, tips can be pooled and split across the entire pay period or paid directly to the employee that collected the tip. We are looking to build out additional tip splitting options in the future and splitting tips across shifts is one of our top requests as you can see from additional comments below!


Square Payroll integrates with Homebase. Make sure that your Square and Homebase accounts are connected in the Apps section of your online Square dashboard. Your employees can continue to clock in/out directly from Homebase. All timecards will automatically transfer over to Square in the timecards section. Any timesheet adjustments or deletions will automatically update to Square in real-time. When it’s time to run payroll you can then seamlessly import your employees’ timecards with the click of a button. We automatically calculate regular and overtime hours.


Thanks again for these questions! 😀

Message 8 of 93
Pesso Super Seller

Re: Live Q&A: Ask us anything about Square Payroll

@caroline Thanks so much! Huge help!


For Homebase, I already have homebase accounts set up for my employees - can I import my Employees from Homebase into Square so they maintain their homebase accounts?
When I make new employee accounts in the future, do I make them in Square first or in Homebase?


I saw there are 2 places to connect Square and Homebase - as the POS and the Payroll provider.
Can I just connect Square as my Payroll provider and will that work for syncing employees?



Message 9 of 93

Re: Live Q&A: Ask us anything about Square Payroll

Jumping in for Caroline! 


She recommends connecting your Square and Homebase accounts from your online Square dashboard. If you navigate to the Apps section, you can find Homebase under the Employee Management Category. Select "Get Started" and you will be prompted to login to your Homebase account. One the setup is complete, your employees, timecards and Payroll will sync.


Your employees will also be able to maintain their existing Homebase accounts. In the future when you add a new employee, add them directly to Square and we will import their information over to Homebase. Any changes made in your Homebase account will update to your Square account.


If you need assistance syncing the two, you can reach out to Homebase support by calling (415) 361-5685 between 7am-7pm Pacific Time, Monday to Friday.

Message 10 of 93