Senior US Payroll Specialist

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy. We are seeking a Senior Payroll Specialist 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 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. A day in the life (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 our internal and external customers who have payroll inquiries. Manage and respond to ServiceNow tickets accurately on the first instance. Proactively ensure all errors and issues are being resolved as indicated in 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 the 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-2’s, T4’s) 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 the number of payroll-related errors. Determine the root cause of payroll errors by collecting and analyzing information under strict deadlines. Assist with the 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 the accounting team to assist with complex variance queries and balance sheet reconciliations, drawing on 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. 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. This must include executing EIB data loads, release and regression testing, and troubleshooting configuration or calculation issues. Regional Expertise: In-depth working knowledge of NAM payrolls (US, Canada & 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. US payroll certifications such as FPC (Fundamental Payroll Certification) or CPP (Certified Payroll Professional) are a plus. 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 Smart Compliance, Cloud Pay, ServiceNow, or similar global payroll and tax software. AI at Toast At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture. Our Total Rewards Philosophy We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits . How Toast Uses AI in its Hiring Process Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. We ask that you complete interviews and assessments on your own, without real-time AI tools, recording, or transcription bots, unless we tell you otherwise in advance. To learn more: https://careers.toasttab.com/ai-in-hiring Our Approach to Hybrid Working We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in-office expectations by region: https://careers.toasttab.com/locations-toast People Are the Secret Ingredient in Our Recipe for Success At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry brings together people with a wide range of backgrounds, experiences, and perspectives, and we value that same breadth at Toast. We strive to build a culture grounded in authenticity, respect, and humility, where every Toaster has a real opportunity to grow, contribute, and do their best work—raising the bar in delivering exceptional experiences for our customers and each other. Apply today! Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact candidateaccommodations@toasttab.com . ------ For roles in the United States, 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.