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Live Q&A: Ask us about Benefits through Square Payroll

On July 30th at 11am PST, we hosted a Live Q&A about Benefits through Square Payroll here on the Seller Community.


We answered questions about health insurance, 401(k), workers’ compensation, and pre-tax benefits. Our industry-leading providers offer comprehensive benefits for all types of businesses and budgets. 


Curious on why or how to offer a certain benefit? We invited specialists from our benefit partners to answer these questions for you!


Here are a few example questions: 

  • What considerations should I make before offering health insurance? 
  • Do employers lose money by offering pre-tax benefits? 
  • What loss does workers’ compensation insurance cover/not cover? 
  • How do deductions work and when are those made? 
  • What is a Safe Harbor (401k) plan? 




Message 1 of 17
1 Best Answer

Accepted Solutions
SydneyCohen Square

Re: Live Q&A: Ask us about Benefits through Square Payroll

Best Answer

Thank you to everyone for joining us and asking some great questions today! Our benefits offering is just another way Square Payroll gives you the tools you need to grow your business. With benefits accessible through Square Payroll, you can provide “big company benefits” to your employees and to yourself! 


We partner with @GUIDELINE401K, @SimplyInsured, @AP_Intego, and @Alice-Pretax to provide 401(k), health, pre-tax benefits, and workers’ compensation, respectively. Our partners answered questions about each of their benefits offerings and love providing their expertise and hearing feedback from all of you, so please keep the questions and suggestions coming! 


Here’s my summary of the themes that we saw in today’s Q+A: 


  • Affordable benefits: We’ve partnered with Guideline, SimplyInsured, Alice, and AP Intego because all four are forward-thinking about the way they approach their respective benefits. Each of our partners take an innovative and technology-led approach to benefits, which, amongst other things, drives down the cost for employers that want to provide them. With features like pay-as-you-go workers’ compensation or pre-tax benefits that have no out-of-pocket cost (you can actually save money), we’re making benefits accessible and within budget.  
  • The best option for your employees: We made our benefits offerings completely customizable so you can pick the benefits your employees want most. If you don’t know which benefits your employees want, you can ask them directly or conduct a survey. There are also certain labor laws that may require you to provide certain employee benefits, so be sure to check your local labor laws to ensure you’re staying compliant. 


Thank you again to everyone that participated in today’s Q+A! And a special thanks to our partners for joining us to answer your questions about Square Payroll’s benefits. 


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Message 17 of 17

Re: Live Q&A: Ask us about Benefits through Square Payroll

How do I know if I’m eligible to offer health or 401(k) benefits to my employees?

Message 2 of 17

Re: Live Q&A: Ask us about Benefits through Square Payroll

A 401(k) is an employer-sponsored retirement plan, so the only real restriction is that only employers can offer one. This means that you pay W-2 employees, or you are your own employer (you earn self-employed income). There is no minimum number of employees needed to start a plan. 

Right now Guideline (our 401(k) provider through Square Payroll, is giving employers 3 month free when you set up a new Safe Harbor 401(k) if you want to learn more, visit this link: guideline.com/safe-harbor.

Message 3 of 17

Re: Live Q&A: Ask us about Benefits through Square Payroll

I'm not asking about Benefits specifically. I have a general question about Square Payroll which I have been trying to get a clear definitive answer on for over a year now with no luck. I have a bookkeeping client opening a pizza place who will use Square and wants to use Square Payroll as well. But, we need to know if Square Payroll will work with QuickBooks Online SIMPLE START specifically. I've been assured Square Payroll will work with QuickBooks Online but there are various versions of QuickBooks Online and I have never been completely confident in the answers from anyone that Square Payroll will work with the Simple Start version of QuickBooks Online without requiring purchase of QuickBooks Payroll or a more expensive version of QuickBooks Online. Can you please give me s definitive and actually well researched answer to this question rather than just an offhand sales pitch reassurance? Thanks.

Message 4 of 17
SydneyCohen Square

Re: Live Q&A: Ask us about Benefits through Square Payroll

Hi @Marcella - Square Payroll syncs with Quickbooks Online. The Simple Start variation of Quickbooks does sync with banks and apps. If you want step-by-step instructions on how to integrate Quickbooks with Square Payroll, visit this support article.


Let me know if this answers your question!

Message 5 of 17

Re: Live Q&A: Ask us about Benefits through Square Payroll

If we offered health insurance through our company to our employees, would that prevent them from getting a subsidy if they chose to purchase from Healthcare.gov or do they even have the option to purchase from them then?  Does it make any difference if we pay a certain percentage of the cost vs all of it?

Message 6 of 17
SimplyInsured Partner

Re: Live Q&A: Ask us about Benefits through Square Payroll

Great question, @JAFloydAn individual is not eligible for Healthcare.gov subsidies if they are offered a plan by their employer that is considered “affordable” by Affordable Care Act standards. For 2019, “affordable” is defined as costing less than 9.86% of the employee’s gross income, based on the employee’s share of the premium. So, if your company pays for 100% of the premium, then the plan would automatically be deemed affordable, and the employee would not qualify for subsidies on plans sold through healthcare.gov. If you pay only a portion of the cost, then you will need to calculate the employee’s portion as a percent of their gross income to determine whether it’s considered affordable.

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Should you offer benefits to all employees after a certain employment timeframe? How much is the minimum to put towards their benefits to make it worth while for everyone? 

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SydneyCohen Square

Re: Benefits

Hey @Colies - Depending on your location, the size of your company, and the kinds of employees you have (1099, W-2, etc.), there are different labor laws that may or may not mandate you to provide benefits to your employees. How much you contribute also is dependent on your budget, the size of your business, and the benefits you plan to offer. We recommend that you consult a financial professional on how much you should contribute based on what’s best for you.

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Hawaii benefits

When will Square benefits (health) be available in Hawaii?

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