Payroll & People Generalist

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About the Role

As Headway’s Payroll & People Generalist, you’ll be a critical member of our growing People Ops team, helping us deliver a seamless employee experience while ensuring operational excellence across payroll, compliance, and employee support. You’ll primarily support payroll processes, while also partnering with our Benefits, HR Compliance and HR Business Partner (HRBP) functions to drive high-impact work for our team of 750+ employees.

This is an ideal role for someone with strong payroll and HR generalist experience who’s looking to continue to deepen their skills in these areas, as well as expand to HR compliance and employee programs at a high-growth, mission-driven company.

You will:

• 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.

You’d be a great fit if:

• 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

Compensation and Benefits:

• The expected base pay range for this position is $84,000 - $124,000, based on a variety of factors including qualifications, experience, and geographic location.

  We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Benefits offered include:

• 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