Payroll & People Generalist

Summary

Join Headway's People Ops team as a Payroll & People Generalist and play a critical role in ensuring a seamless employee experience. You will support payroll processes, partner with other teams, handle employee inquiries, maintain internal resources, assist with compliance tasks, and identify opportunities for process optimization. This role requires 3+ years of payroll processing experience, People Operations experience, and exposure to HR compliance. The ideal candidate thrives in a fast-paced environment, possesses a strong sense of ownership, and is comfortable working with HRIS and payroll systems. Headway offers a competitive total rewards package including robust health and wellness benefits, retirement savings, and equity. The company is committed to diversity and inclusion and offers remote work options.

Requirements

• You have 3+ years of experience in payroll processing, with demonstrated ownership of core payroll duties such as auditing, reconciling, and troubleshooting
• You have experience in People Operations, with hands-on ownership of employee data updates, inquiry management, and cross-functional support across People Ops, HRBPs, and Total Rewards
• You have exposure to HR compliance and/or HRBP programs and are eager to grow your skillset in these areas
• You thrive in a high-growth, fast-paced environment and enjoy building repeatable systems
• You have a strong sense of ownership and accountability for your work, and a natural service mindset when supporting employees
• You are comfortable working with HRIS and payroll systems (Workday & OSV experience is a strong plus)
• You have a sharp eye for detail and are confident working with data, spreadsheets, and documentation

Responsibilities

• Support Payroll Operations by partnering with the Payroll Lead to process bi-weekly pay cycles in Workday, perform regular payroll audits, manage tax notices, and ensure compliance with regulations
• Coordinate with People Operations, HRBPs, Total Rewards, and Finance teams to ensure accurate employee data updates, journal entry support, and seamless month-end payroll close
• Own Tier 1 People-support tickets, respond to employee inquiries related to payroll, benefits, and People Ops programs, and escalate complex issues as needed
• Maintain internal employee resources and documentation based on recurring inquiry themes and support training completion tracking across the organization
• Partner with HRBPs on lifecycle and offboarding logistics including severance agreements administration and performance documentation
• Assist with compliance-related tasks including training administration, documentation, audits, and ad hoc projects to ensure consistent recordkeeping and regulatory alignment
• Identify opportunities to automate workflows and optimize manual processes across payroll and People Operations

Benefits

• Equity Compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development