I have a super similar business to this and have the same issues. 20 events annual, about 40 contractors per event with about 10 that are first time staff members. I'm looking for a streamlined and affordable process.

Thanks for posting this! Also a massage business here, struggling with ALL payroll providers, including Quickbooks. Considering a switch to Square but I’m currently uncertain. Microsoft Excel and Venmo are my go-to because no one else seems to offer simple software solutions for simple businesses.

Hi @TheMassageTeam , @Clinton_Grider , @brbmassage ,

Thanks for your comments and for walking us through your thought process. Apologies for the delayed response here. I wanted to ensure I had all the correct information for you.

If you have a small business that pays contractors only, I understand the appeal of trying to take a “DIY” approach to payroll by using some of the peer-to-peer payment tools mentioned above. That being said, there are a few benefits of using a tool like Square Payroll over those methods. I will try and outline them for you below:

1. Cost can stay low: If you are only paying contractors, Square Payroll has a contractor-only plan that allows you to pay-as-you-go. You would only pay $6 per person paid each month, but you can pay them as many times as you want within that month at no extra cost. Ex: if you pay one massage therapist once per week (4 times over the month), you are still only paying $6 that month.
2. Reducing errors with tax calculations: Square Payroll will manage your payroll tax calculations and supply 1099-NEC forms to your team members at year end with the contractor-only plan. If you ever were to upgrade to the full-service plan then we also will file and pay your payroll taxes on your behalf.
3. Easier accounting and reporting: Alongside the 1099-NEC forms that are supplied to your contractors, Square Payroll also makes recording and exporting payroll history records much easier. So you can keep track of all those payments you make over the year.
4. We can scale with you as you grow: Even if you start with contractors, over time it will be easy for you to start paying W2 employees or expand your team if you are already set up and running with Square.

*Using EIN instead of SSN for contractors - we have a workaround for this

• Even though it is not advertised in the current Square Payroll system, we do have a workaround that will allow you to enter an EIN instead of an SSN. You may still pay contractors with EINs by entering their EIN in the SSN field. It is not something we promote to all sellers since we are working on product improvements that will make this experience easier and more clear in the future. However, if you call our support center they can give you the instructions or you can DM me here on the Seller Community and I can provide them as well.

Thank you, Ryan, this is super helpful! Looking forward to the webinar.

Thanks Ryan; this is just what I was looking for; Unfortunately, I won't be able to attend the webinar, but I will watch the video; Best,

Great to hear @Lovewell ! 😄 If there's any part of the experience you find causes some confusion or you wish was better, feel free to DM me about it.

Hi @capers,

Thanks for reaching out. There are no fees associated with onboarding or switching, but I'll outline the cost of our Square Payroll plans below.

Full-service payroll: $35 per month + $6 per person paid each month (pay them as many times as you want within the month)

• Pay W2s and 1099s - unlimited pay runs per month at no extra cost
• Get automated tax filings
• Timecard importing and scheduling up to 10 days out
• Run auto-payroll
• Faster pay speeds like two-day pay or next-day pay
• Digital delivery of W2 and 1099-NEC forms at year-end

Contractor-only payroll: $6 per person paid each month (pay them as many times as you want within the month)

• Pay 1099s only - unlimited pay runs per month at no extra cost
• Timecard importing
• Automatic payroll tax calculations
• Digital delivery of 1099-NEC forms at year-end

You can review these plans in more detail on our pricing page. 

Checking back in with anyone subscribed to this post! 🚨 The recording of this event is now available: New Year, New Payroll: Why This is the Best Time to Switch - Event Recording. You can watch it anytime in the Video Library! ✨

@BofBArtStudio @isavvydesigns @BakerA