Senior NAM Payroll Specialist

We are seeking a Senior Payroll Specialist (North America) to join our in-house North America (NAM) payroll team.

This is a high-impact, hybrid role that owns the most complex payroll processing, escalations, and systems and compliance initiatives, while overseeing and reviewing the day-to-day transactional work delivered by the Payroll Specialist team.

As part of Toast’s internal payroll organization,not a third-party payroll bureau or outsourced provider,you will act as a subject-matter expert across payroll operations, compliance, and systems; mentor Payroll Specialists and help prepare them for advancement; and serve as a key backup to the Payroll Team Lead.

Based in India, this position supports payroll for employees in the NAM region; it does not involve India payroll processing.

Key Responsibilities

• Payroll Operations & Volume: Oversee accurate and timely processing of bi-weekly multi-state payrolls for more than 5,700 employees across the US, Canada, and Mexico, with day-to-day transaction processing primarily executed by the Payroll Specialist team.
• Personally owns and processes the most complex, escalated, and Mexico payroll cycles.
• Complex Transactions & Global Mobility: Own complex and escalated payroll transactions that fall outside standard Specialist-level processing, including benefits-in-kind processing and overpayment calculations and repayments.
• Coordinate with third-party consultants and Global Mobility to input transferred employees’ payroll information accurately and in a timely manner.
• Employee Ticketing & Tier 2 Support: Support internal and external customers with payroll inquiries.
• Manage and respond to ServiceNow tickets accurately on the first instance.
• Proactively ensure errors and issues are resolved in line with the Service Level Agreement (SLA).
• System & Data Management: Ensure Workday is maintained as the primary source of data integrity.
• Responsible for Workday EIB (Enterprise Interface Builder) mass data uploads, global mobility transactions, and serving as lead tester for User Acceptance Testing (UAT) and semi-annual Workday system releases.
• Reporting & General Ledger: Review and analyze payroll and data analysis reports, including those generated by the Payroll Specialist team, to ensure audits are completed accurately and on time.
• Maintain and reconcile General Ledger accounts, ensuring accounts are balanced.
• Create content for dashboards and metrics as needed.
• Compliance, SOX & Audits: Work with the Payroll Team Lead on quarterly reviews of the SOX (Sarbanes-Oxley) payroll process and support Internal Audit requirements.
• Manage audits for 401K (US retirement savings plans), ESPP, Workers’ Compensation, and review/approve monthly, quarterly, and annual equity audits.
• Review annual tax statements (W-2s, T4s) for all expatriate personnel to ensure accuracy.
• Vendor Management & Tax Filings: Coordinate with ADP SmartCompliance and CloudPay on tax filings, notice resolutions, and reconciliations.
• Own ADP tax-registration administration, including applying for new SIT, SUI, and local tax IDs and maintaining accurate payroll tax records.
• Process Prior Quarter/Prior Year Tax adjustments as needed.
• Manage responses to all tax agency inquiries through ADP Tax Service and CloudPay.
• Process Improvement & Troubleshooting: Audit current processes to reduce payroll-related errors.
• Determine root causes of payroll errors by collecting and analyzing information under strict deadlines.
• Assist with development and final review of payroll policies, workflows, knowledge bases, and contingency plans.
• Maintain and update Standard Operating Procedure (SOP) documentation, which is under the care of the Specialist.
• Cross-Functional Collaboration: Work closely with Accounting to assist with complex variance queries and balance sheet reconciliations, using supporting data and documentation prepared by the Payroll Specialist team.
• Partner with Total Rewards to ensure smooth integration of payroll with other HR functions.
• Leadership & Mentorship: Assist the Payroll Team Lead with training and mentoring the payroll team, including onboarding, upskilling, and preparing Payroll Specialists for advancement into the Senior Payroll Specialist role.
• Serve as a primary backup for Payroll Specialists.

What you'll need to thrive (Requirements)

• Education: Bachelor’s degree or equivalent practical payroll experience preferred.
• US payroll certifications such as FPC (Fundamental Payroll Certification) or CPP (Certified Payroll Professional) are a plus.
• Experience: 8+ years of hands-on payroll processing experience, including 4+ years working directly in Workday, and ownership of complex, high-volume payroll cycles across multiple jurisdictions.
• US Workday Payroll & Absence Proficiency (Hard Requirement): Demonstrated hands-on experience processing US payroll and absence management in Workday is required.
• Regional Expertise: In-depth working knowledge of NAM payrolls (US, Canada, and Mexico), including multi-jurisdiction statutory and year-end requirements.
• In-House / Corporate Payroll Environment: Demonstrated experience operating within an in-house or corporate payroll function, as opposed to a third-party payroll bureau or BPO, including direct partnership with internal stakeholders (HR, Total Rewards, Accounting) and end-to-end ownership of the payroll process.
• Work Environment & Soft Skills: Ability to work independently as part of a team in a fast-paced environment and deliver results against deadlines, including performing effectively under sustained pressure.
• Shift Commitment: Willingness and ability to work aligned to US Eastern business hours on an ongoing basis, including adapting to US daylight saving time transitions.
• Leadership: Experience mentoring, training, or providing technical guidance to junior payroll staff.

Preferred Qualifications

• Escalation Ownership: Experience acting as the primary point of escalation for complex payroll issues within an in-house or corporate payroll team.
• Advanced Tools: Experience leveraging AI-powered reconciliation, analytics, or reporting tools (e.g., automated exception management, intelligent transaction matching, AI-assisted dashboards) to strengthen audit readiness.
• Software Familiarity: Familiarity with ADP SmartCompliance, CloudPay, ServiceNow, or similar global payroll and tax software.