Set up health insurance benefits with SimplyInsured
About health insurance with SimplyInsured
Square Payroll partners with SimplyInsured to allow employers to offer medical, dental, and vision insurance to their employees.
SimplyInsured integrates seamlessly with Square Payroll, and all contributions and deductions sync automatically each pay run. 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.
Before you begin
Employers can enroll in SimplyInsured directly from their Square Dashboard and pick the health plan that best fits them and their business.
SimplyInsured is a separate insurance partnership from the direct-to-employee benefits Learn more about how to add employee benefits with Square Payroll.
Premiums depend on a variety of factors including the plan type, state, and age of employees. The company must contribute at least 50% of the premium.
SimplyInsured is currently available in all states except Hawaii, Minnesota, North Dakota, South Dakota, Vermont, and the District of Columbia.
For more information, contact SimplyInsured at 855-409-5767, email SimplyInsured at [email protected], or visit the SimplyInsured website.
Set up health insurance benefits with SimplyInsured
Sign in to Square Dashboard and go to Staff > Payroll, then select Benefits.
Find the Health Insurance tile and click Get Started.
Select Start Setup to start the process with SimplyInsured. Square Payroll syncs your business information with SimplyInsured to provide you with an instant quote.
Choose the best plan and complete the health application online within SimplyInsured.
Once approved, your employees will receive an invitation to enroll in coverage within their Square Payroll employee dashboard.
Report S-Corp owner health insurance premiums
For S-Corporation shareholders who own more than 2% of the business, health and accident insurance premiums paid by the company are subject to special IRS reporting rules. These premiums must be included in the employee's Form W-2 Box 1 (Wages, tips, other compensation), but excluded from Boxes 3 and 5 (Social Security and Medicare wages). To correctly report S-Corp owner health insurance premiums:
Mark applicable employees as Owners within their employee profile in Square Payroll. Learn how to add team members to Square Payroll.
Track owner health insurance premiums outside of Square Payroll throughout the year.
Complete the Square Payroll year-end checklist, which is available in the Payroll tab in Square Dashboard from late November through December.
Enter the total premiums paid for each owner as part of the year-end process.
Square Payroll will use this information to apply the correct W-2 reporting treatment by including the premiums in Box 1 while excluding them from Boxes 3 and 5.
Note: Do not run S-Corp owner health insurance premiums through regular payroll as a benefit or deduction. The available benefit options are intended for pre-tax employee health insurance plans and do not support the specialized W-2 reporting requirements for S-Corp owners.