Toast Payroll: Get Started With SimplyInsured

Last updated: Apr 8, 2026, 10:20 AM

Toast Payroll Pro offers customers a way to get in touch with health, vision, and dental benefits through SimplyInsured.

This article only applies to customers who are using SimplyInsured through Toast Payroll Pro. This does not apply to customers using the Classic Benefits module (Legacy Customers Only) or customers using the deductions-only method.

 

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Benefits Through SimplyInsured and Toast Payroll Pro

Toast is partnered with SimplyInsured, a benefits broker, to help you get quotes, compare plans, and enroll in different types of health coverage for you and your employees. SimplyInsured has a licensed support team that can help guide you toward plans for your situation and answer any questions along the way.

 

You must have Toast Payroll Pro in order to set up SimplyInsured benefits.

 

  • If you don't have a Toast Payroll subscription at all, you can add it as a new service. To see what SimplyInsured offerings exist, refer to the SimplyInsured + Toast website.
  • If you have Toast Payroll Essentials and want to upgrade to Toast Payroll Pro, navigate to Benefits and select Get a demo.

 

You need an HR+/Admin security role to access SimplyInsured. If you have a custom security role in Toast Payroll, you might not be able to access the Benefits tab. If you think you should have access, contact us via the blue chat dot in the lower-right corner of any Toast Payroll page to resolve this.

 

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Set Up SimplyInsured Benefits

You can sign up with SimplyInsured whether you have an existing plan/broker or not. Begin by navigating to the Benefits tab in Toast Payroll. Then follow the instructions below:

 

 

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Onboard Employees to Benefits With SimplyInsured

Your employee must be hired into Toast Payroll in order to enroll in benefits with SimplyInsured via Toast Payroll.

 

  1. When you sign up for a SimplyInsured plan, you can configure employee eligibility requirements within the SimplyInsured portal.
    1. You can base eligibility on items like the length of employment, employment status, and/or the company's and/or state's requirements.
  2. If eligible, employees will receive an email from SimplyInsured sent to the email on record in Toast Payroll. The email will be sent from toastsupport@simplyinsured.com and the subject line will be "[SimplyInsured] Action Required: Your [company name] Health Insurance Application".
    1. You can set a delay for how soon eligible employees receive an automated invite (e.g. 90 days after hire in Toast Payroll).
    2. Alternatively, you can set a "trigger event" that you may base on other eligibility factors, such as hours worked for the company. Once the trigger has been reached, that will send the employee an automated invite email.
  3. When it's time for employees to complete their enrollment, whether they accept or decline, refer to Toast Payroll: Employee Enrollment in SimplyInsured Benefits.

 

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SimplyInsured Onboarding FAQ

How do I log into SimplyInsured?

Navigate to Benefits > View and manage health benefits and select an FEIN from the Active benefits tile. Access is limited to HR+ users.

 

Employees can use Toast Payroll: Employee Enrollment in SimplyInsured Benefits as their guide.

 

How can I contact SimplyInsured?

SimplyInsured's email address is toastsupport@simplyinsured.com. They can also be reached via phone at 800-610-4923 from 9:00 a.m. - 8:00 p.m. EST Monday through Friday.

 

How can I check if my employees were invited or are eligible for benefits?

Once you've signed up for a new plan or connected your existing plan/broker, navigate to Benefits > View and manage health benefits and select an FEIN in the Active benefits tile. After logging into SimplyInsured, you'll see a list of employees on your dashboard that are a part of one or both categories.

 

Can I configure employee eligibility?

Employees will be eligible based on the criteria you set on the SimplyInsured portal. You can:

 

      • Set a delay for how soon eligible employees receive an invite
      • Manually trigger invites for employees
      • Trigger invites based on eligibility events such as new hire, hours worked, etc.

 

How will an employee's SimplyInsured plan show up in Toast Payroll?

Employee deductions will match the pay frequency of their primary job. These deductions will be applied automatically and can be found as a recurring deduction by navigating to the employee's profile > Recurring > Deductions. You can easily recognize SimplyInsured deductions because they will begin with "SimplyInsured".

 

Am I allowed to set up different enrollment tiers through SimplyInsured?

Yes, you can set up multiple tiers per FEIN.

 

What do I need to know about open enrollment, annual health insurance renewal, and changing or updating health coverage plans?

Use The SimplyInsured Guide to Your Annual Health Insurance Renewal (external link) for a comprehensive look at each of these items and more.

 

How do I pay my company's insurance premiums?

This is done automatically through the SimplyInsured portal via Toast Payroll once you sign up for a plan. Customers can contact SimplyInsured via email at toastsupport@simplyinsured.com or via phone at 800-610-4923 for questions about billing. Billing for company insurance premiums will appear under the name of the carrier that you select to provide benefits.

 

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Additional Resources

 

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Insurance policies available through Ten 250 Corporation, dba SimplyInsured, pursuant to its licenses. Neither Toast, Inc., nor any of its affiliates or subsidiaries, sells or underwrites insurance. However, Toast Insurance Services, Inc. (“TIS”) maintains various insurance licenses and may receive compensation in connection with policies purchased through SimplyInsured. Not all applicants may qualify. Coverage examples are for illustrative purposes only. Your policy documents govern, terms & exclusions apply.

 

This content is for informational purposes and is not intended as legal, tax, HR, or any other professional advice. Please contact an attorney or other professional for advice.