Start with a federal Employer Identification Number if you don’t have one. Apply through the IRS website and you’ll receive it immediately. You need this before you can register with Massachusetts or process any payroll.

Register with the Massachusetts Department of Revenue for withholding tax. File Form TA-1 to get a withholding account number. Massachusetts requires employers to withhold state income tax from employee wages based on exemptions claimed on the employee’s M-4 form.

Register with the Massachusetts Department of Unemployment Assistance. You’ll need a DUA account to file quarterly wage reports and pay unemployment contributions. New employers typically pay around 2.42% on the first $15,000 of each employee’s wages annually, though rates vary by industry and experience rating.

Set up Paid Family and Medical Leave contributions. Massachusetts requires PFML contributions from both employers and employees. As of 2024, the combined rate is 0.88% of wages. Employers can deduct the employee share from paychecks and remit the total to the Department of Family and Medical Leave quarterly. This is easy to miss because not every state has it, but Massachusetts enforces it.

Collect employee paperwork before the first paycheck. You need a federal W-4 for federal withholding, a Massachusetts M-4 for state withholding, an I-9 to verify work eligibility, and direct deposit authorization if you’re paying electronically. Keep these on file and update them when employees request changes.

Choose how you’ll run payroll. Manual calculation works if you have one or two employees and understand the math, but mistakes are easy and costly. Payroll software like QuickBooks Payroll or Gusto automates calculations, tax deposits, and quarterly filings. Full-service payroll providers handle everything so you just approve hours and employees get paid correctly. Many owners providing small business bookkeeping in MetroWest Massachusetts find that outsourcing payroll removes a significant compliance burden.

Get workers’ compensation insurance before you hire anyone. Massachusetts requires coverage for most employers. Rates depend on your industry classification and claims history.

Make tax deposits on schedule. Federal payroll taxes deposit monthly or semi-weekly depending on your total liability. Massachusetts withholding follows a similar schedule. Miss a deposit deadline and penalties start immediately.

File quarterly reports. Form 941 goes to the IRS. Massachusetts requires quarterly withholding returns and DUA wage reports. Year-end brings W-2s for employees and reconciliation forms for all the agencies involved.

The process isn’t complicated in theory, but Massachusetts has more moving parts than some states with PFML, DUA, and the various registrations required. Getting it wrong means penalties, unhappy employees with incorrect paychecks, and compliance problems that compound over time. Most small businesses either use payroll system setup services to configure everything correctly from the start or outsource payroll entirely to avoid the ongoing compliance burden.