System updates

We’re experiencing issues that may affect your Square services. We’ll continue to update our status page with more information.


Payroll 401(k) Benefits

Square Payroll partners with Guideline so that you can offer 401(k) retirement benefits to your employees. It’s easy to setup and works in the background when you process payroll.

How it Works

Employers can enroll in Guideline directly from the Benefits tab of their Payroll dashboard and seamlessly offer retirement benefits. Guideline makes 401(k) plans easy by handling all of the onboarding of your employees, administration, compliance, and investment management. Guideline allows employees to make both traditional pre-tax 401(k) contributions as well as post-tax roth 401(k) contributions. When you process payroll through Square, all contributions and deductions sync automatically each pay run.

Guideline is a separate insurance partnership from the direct-to-employee benefits that are accessible to payroll team members through the Square Team App. Learn more about direct-to-employee benefits in our Support Center.

Sign Up with Guideline

  1. Visit the Benefits tab of your Payroll dashboard.

  2. Click Get Started on the Retirement tile.

  3. Click Start Setup. Square Payroll syncs your business information with Guideline.

  4. Enroll in the plan and decide how much (if at all) to contribute.

  5. Eligible employees will receive an invitation to enroll in the 401(k) account on their online Square Payroll Employee Dashboard and a welcome email from Guideline.

Run Payroll with a Retirement Plan

Once your employees have enrolled in the retirement plan, all contributions and deductions are automated each pay period. To process payroll

  1. Log in to the Payroll section of your online SquareDashboard or Square Payroll app > click Pay Employees as usual.

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

  3. Employee deductions and employer contributions will appear on the Adjustments screen. You are able to edit the employee deduction if needed. Note: Changes to the employer contribution will need to be made directly in Guideline.

  4. Click Continue to proceed with processing payroll.

Guideline will debit for the full 401(k) amount (company contribution and employee deferral) the business day after payroll is processed.


How much does Guideline cost?

Guideline’s plans start at $49/mo + $8 per active participant per month. There are no separate transaction fees for rollovers, disbursements, and loans.

The cost for participants is 0.08% per year*, which comes out to $0.67 a month for an account with a $10,000 balance**.

*The annual account fee of 0.08% applied to assets under management is calculated and deducted on a monthly basis at 1/12 the annual stated rate (0.08%) based on the account balance on the last day of each month.

**This information is for illustrative purposes only and does not represent the actual costs you may incur as a Guideline client. Information shown here assumes a static balance of $10,000 per month, an annual account fee of 0.08% on assets under management (calculated and deducted on a monthly basis at 1/12 of the annual stated rate (0.08%) based on the month-end account balance, and does not account for common factors that affect the value of your account balance over time such as gains, losses, distributions, additional contributions, etc., and is not intended to constitute investment advice nor an assurance or guidance of future performance. The fee presented does not include other fees that a 401(k) participant may incur, including from mutual fund expense ratios and a monthly maintenance fee to participants who end employment.

What are company contributions?

Employers can make contributions through Guideline’s easy to use employer dashboard. Contributions are calculated pre-tax. You can contribute a percentage of an employee’s gross pay or match an employee’s contribution. Guideline also supports profit sharing contributions.

Who is eligible for a 401(k)?

When an employer sets up a retirement plan, you can set eligibility criteria in Guideline based on minimum age and length of tenure. Once those criteria are met, the employee becomes eligible and is invited by Guideline to enroll.

How can I update employer and employee contributions?

Any changes to contributions should be made in Guideline directly. Any updates will be processed on the next pay run.

How can I switch 401(k) plans to Guideline?

If you already have a 401(k) and want to switch to Guideline, you will need to reach out to the Guideline Sales team directly at or request a call through their scheduling page.

How do I contact Guideline?

For more information, please contact Guideline at 888-228-3491 or email

Learn more about: Payroll

Can't find what you need?