North America Payroll Lead

Cielo Projects•Boston, MA

3d•$80,000 - $100,000•Hybrid

About The Position

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

Requirements

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.

Nice To Haves

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.

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, supporting 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 effective vendor performance, SLA management, project deliverables, issue resolution, and continuous improvement.
Serve as the payroll subject matter expert for North America, partnering closely with HR, Finance, Legal, Benefits, Compensation, and external vendors.
Support payroll inputs and employee lifecycle events, including 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, and 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 to support compliance and operational scalability.
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.