North America Payroll Lead

Overview

The organization is seeking a North America Payroll Lead to manage payroll operations across the U.S., Canada, Mexico and limited EOR-supported populations. This role oversees payroll delivery for a multi-country employee population, ensuring payroll accuracy, compliance, timely processing, strong vendor management, and operational excellence—specifically including support for month-end, quarter-end, and year-end payroll-related financial close activities and payroll audits.

Responsibilities

• Lead end-to-end payroll operations across North America, including the U.S., Canada, Mexico, and limited EOR-supported populations.
• Ensure payroll is processed accurately, timely, and in compliance with applicable federal, state/provincial, local, and country-specific payroll, tax, labor, and statutory requirements across 30+ U.S. states and multiple Canadian provinces.
• Serve as the primary payroll lead for Workday Payroll, including payroll processing, configuration, testing, audits, reporting, integrations, releases, system changes, data validation, and ongoing process optimization.
• Manage payroll delivery through internal processes, third-party payroll providers, and Workday implementation/support partners, ensuring vendor performance, SLA management, project deliverables, issue resolution, and continuous improvement.
• Act as a payroll subject matter expert for North America, partnering with HR, Finance, Legal, Benefits, Compensation, and external vendors.
• Support payroll inputs and employee lifecycle events: new hires, terminations, transfers, leaves of absence, bonuses, equity-related payments, benefit deductions, and other payroll adjustments.
• Oversee payroll impacts of stock/equity transactions, executive compensation, retention bonuses, relocation benefits, taxable fringe benefits, and other complex compensation programs.
• Partner with Finance on payroll accounting, balance sheet reconciliations, accrual calculations, variance analysis, funding, reporting, SOX-compliant controls where applicable, and month-end, quarter-end, and year-end close activities.
• Manage year-end payroll activities, including:
  • U.S. W-2
  • Canada T4/T4A/Relevé 1
  • Mexico annual reporting
  • statutory obligations, payroll audits, tax statements, and employee inquiries.
• Develop and maintain payroll policies, SOPs, process documentation, governance frameworks, controls, and audit-ready processes.
• Support international expansion activities, including new state/province registrations, entity setup support, and oversight of EOR payroll arrangements where applicable.
• Establish and track payroll KPIs, service levels, audit findings, compliance metrics, and continuous improvement initiatives to streamline payroll processes, improve data quality, reduce manual work, and strengthen cross-functional workflows.

Qualifications

• 7+ years of progressive payroll experience, including independent ownership of multi-state, multi-jurisdiction payroll operations for geographically dispersed workforces, with exposure to Canada and/or Mexico payroll.
• Hands-on Workday Payroll experience required, including payroll processing, testing, reporting, production support, data validation, and issue resolution.
• Strong knowledge of U.S. federal, state, and local payroll requirements, including payroll tax, wage and hour considerations, garnishments, wage attachments, leaves of absence, benefit deductions, multi-state taxation, and year-end processes; familiarity with Canadian and Mexican payroll compliance preferred.
• Strong understanding of payroll accounting, payroll funding, general ledger interfaces, accruals, reconciliations, variance review, controls, and financial close processes.
• Experience supporting internal and external payroll audits, including SOX, statutory, tax, regulatory compliance, and control reviews.
• Experience managing payroll vendors and outsourced payroll providers, including SLA management, service reviews, issue escalation, and contract governance.
• Strong analytical, problem-solving, stakeholder management, and communication skills, with the ability to influence senior stakeholders across HR, Finance, Legal, Tax, Benefits, and external service providers.
• Ability to operate independently in a fast-paced, evolving environment with strong attention to accuracy, confidentiality, and operational follow-through.

Preferred Qualifications

• Workday Payroll certification or advanced experience implementing, optimizing, administering, or supporting Workday Payroll, integrations, and payroll transformation initiatives.
• Experience working with OneSource Virtual managed payroll services.
• Experience supporting payroll operations during M&A, carve-out, stand-up, or broader business transformation initiatives.
• Exposure to global payroll governance, shared services, or payroll center-of-excellence models.
• Certified Payroll Professional (PCP Canada) or equivalent payroll certification.
• Experience supporting payroll operations in high-growth technology or SaaS environments.
• Familiarity with EOR models and international workforce compliance.

Compensation & Benefits

• Competitive benefits and compensation (details not provided).

Location

• Boston, United States – Hybrid
• United States, Canada, Mexico – Hybrid/Remote options available