Payroll Health Insurance Benefits

We’ve partnered with SimplyInsured to give employers the ability to offer medical, dental, and vision insurance to their employees.

Employers can enroll in SimplyInsured directly from their Square Payroll dashboard and pick the health plan that best fits them and their business. SimplyInsured integrates seamlessly with Square Payroll, and all contributions and deductions sync automatically each pay run.

Note: SimplyInsured is a separate insurance partnership from the direct-to-employee benefits that are accessible to payroll team members through the Square Team App. You can learn more about direct-to-employee benefits in our Support Center.

Sign Up with SimplyInsured

  1. Visit the Benefits tab of your Payroll dashboard.

  2. Click Get Started on the Health Insurance tile.

  3. Click Start Setup. Square Payroll syncs your business information with SimplyInsured to provide you with an instant quote.

  4. Choose the best plan and complete the health application online within SimplyInsured.

  5. Once approved, employees will receive an invitation to enroll in coverage within their online Square Payroll Employee Dashboard.

Run Payroll with a Health Plan

  1. Log in to Staff > Payroll in your online Square Dashboard or the Square Team App > select Run Payroll > Pay Employees as usual.

  2. After entering employee hours and any additional pay, select Continue.

  3. Employee deductions and employer contributions will show up on the Adjustments screen. You can edit the deduction amount up or down, but any balance will not roll over into future pay periods. Note: The employer contribution is not editable in Square Payroll and will need to be edited with SimplyInsured directly. If applicable, the employees deduction can be reduced.

  4. Select Continue to proceed with processing payroll.


How much does SimplyInsured cost?

Premiums depend on a variety of factors including the plan type, state, and age of employees. To get a quote, navigate to the health insurance tile on the Benefits tab of your Square Payroll dashboard. The company must contribute at least 50% of the premium.

Are there any additional fees to using SimplyInsured?

No, there are no additional costs for the employer. Plan prices are the same as if you went directly to the health insurance carrier. Premiums are billed by the insurance company monthly.

I hired a new employee. How do I add them to my SimplyInsured health plan?

When you add a new team member to Square Payroll, you’ll be prompted to indicate whether this new employee is eligible for SimplyInsured health benefits. If you indicate they are eligible, they will automatically receive an invitation to enroll in health benefits.

I terminated a employee. How do I remove them from my SimplyInsured health plan?

When you terminate and remove an employee from Square Payroll, the employee will automatically be removed from the SimplyInsured health plan on the first of the month following termination. For example, if an employee is terminated on October 15th, they will be active on the plan through October 31st and removed from the plan on November 1st.

Do I need to offer health insurance to all of my employees?

All full-time employees who work 30+ hours per week are eligible for health insurance. If you choose to cover part-time employees on your health plan, any employees who work 20+ hours per week are eligible. You are not required to offer contractors health insurance.

I’m the business owner, but I don’t see myself in the SimplyInsured quote. How do I add myself to the plan?

Everyone included on the SimplyInsured plan will need to first be added to Square Payroll. Go to the Team tab of your Payroll dashboard > Click Add Team Member. Don’t forget to activate your account and complete all of the required information.

Where is SimplyInsured available?

SimplyInsured is currently available in all states except Hawaii, Minnesota, North Dakota, South Dakota, Vermont, and the District of Columbia.

How do I contact SimplyInsured?

For more information, please contact SimplyInsured at 855-409-5767 or email squaresupport@simplyinsured.com.