Payroll and Systems Administrator (Boston, MA)

About The Role

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.

What You’ll Do

• 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.
  
  

What You Bring

• 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 Have

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

Why Join Us

• Opportunity to shape and improve payroll and HR systems as we scale.
• Collaborative team culture that values innovation and continuous improvement.
• Competitive compensation and benefits package.
• Room for growth into systems administration, HR operations, or payroll leadership.
• Excellent communication skills and a customer-focused approach.
  
  

Our Benefits

Regular full-time US employees are eligible to participate in the following 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
• To learn more, visit winnbenefits.com
  
  

Why WinnCompanies?

A job you can be proud of: WinnCompanies is a nationally recognized leader in apartment community management and development. Our team members are committed to helping people in the communities we serve and making a positive difference in their lives.

A job that challenges you: Our employees are responsible for our growth and success, and we challenge our team members to always be their best in our fast-paced, dynamic and rewarding workplace.

A job you can learn from: We offer multi-faceted leadership and learning opportunities to support our team members’ career growth and professional development.

A team that cares: We value teamwork, innovation, diversity and mutual respect. Through our recognition and rewards programs, we’re committed to celebrating and uplifting our team members.

About Us

WinnCompanies is a mission-driven, national business focused on building and operating top quality affordable housing communities for individuals and families of all incomes, including members of the U.S. Armed Forces and their families. Our people are the source of our success – 4,300 team members working together to create the best possible living communities in 27 states, Washington, D.C., and Puerto Rico.

Whether your skills are in operations, maintenance, leasing, compliance, marketing, IT, HR, accounting or finance, there’s a role for you at WinnCompanies. Your passion for excellence can help us make a positive impact in the lives of real people every day.

If you are a California Resident, please see our Notice of Collection here.

It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Salary will vary based on job responsibilities and scope, geographic location, candidate’s relevant experience, and other factors.

Internal candidates, please apply here: Internal Careers Hub