Payroll and Systems Administrator (Boston, MA)

WinnCompaniesBoston, MA
16h$36 - $46Hybrid

About The Position

WinnCompanies is looking for a detail‑driven, tech‑savvy Payroll & Systems Administrator to join our team in our Boston, MA (Government Center) corporate headquarters. This role is ideal for someone who enjoys the intersection of payroll operations, HR systems, and process optimization. You’ll play a key part in ensuring accurate, timely payroll while supporting the ongoing development and maintenance of our HRIS and related systems. Please note that the pay range for this position is $36.06 to $45.67 per hour, depending on experience. This position offers a hybrid work schedule and will be in-person Mondays-Thursdays with the option to work remotely on Fridays.

Requirements

  • 2 - 5 years of payroll experience, ideally in a multi‑state environment.
  • Hands‑on experience with HRIS or payroll systems (Dayforce, Workday, ADP, UKG, Paylocity, etc.).
  • Strong understanding of payroll regulations, tax rules, and best practices.
  • High attention to detail and a commitment to data accuracy.
  • Ability to analyze and troubleshoot system issues with a solutions‑oriented mindset.
  • Excellent communication skills and a customer‑focused approach.
  • Exposure to reporting tools or basic data analytics.
  • Comfort working in a fast‑paced, evolving environment.

Nice To Haves

  • Experience supporting HRIS implementations or system upgrades.
  • Property management experience

Responsibilities

  • Provide weekly/biweekly payroll support for U.S. employees with accuracy and confidentiality alongside our managed payroll services.
  • Maintain employee records, compensation changes, and payroll data within our HRIS and payroll platforms.
  • Serve as a point of contact for payroll inquiries, resolving issues with clarity and professionalism.
  • Partner with HR, Accounting, and IT to ensure data integrity across systems.
  • Support system configuration, testing, and troubleshooting for HRIS modules (timekeeping, scheduling, onboarding, etc.).
  • Conduct on-going audits and compliance reporting.
  • Identify opportunities to streamline workflows and enhance system functionality to create efficiencies.
  • Ensure compliance with federal, state, and local payroll regulations.

Benefits

  • Generous time off policies (including 11 paid holidays (12 for MA employees); Generous Accrued Time Off increasing with years of service; Generous paid sick time; Annual day of service; Floating Holiday)
  • 401(k) plan options with a company match
  • Various Comprehensive Medical, Dental, & Vision plan options
  • Flexible Spending Account, Dependent Care Flexible Spending Account, Health Savings Account options with HSA annual employer contribution
  • Long Term Disability and voluntary Short Term Disability; Basic Term Life Insurance and AD&D; optional supplemental life insurance
  • Health Expense Reimbursement program (including gym memberships, equipment, and subscriptions)
  • Tuition Reimbursement program and continuous training and development opportunities
  • Wellbeing program (group challenges, seminars, opportunities to earn points to reduce medical premiums), Employee Assistance Program, & Commuter and Parking Reimbursement options
  • Employee Corporate Discount Programs (Verizon Wireless, Home Depot Pro, Staples, and more!)
  • Flexible and/or Hybrid schedules are available for certain roles
  • Employee Relief Program supporting employees with unexpected hardships that place undue financial stress on them and their families
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