Payroll Manager in Winnipeg

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The Manager, Payroll leads payroll operations and the payroll project/change portfolio for approximately 14,000 U.S. employees and 2,000 Canadian employees within a complex, high-volume, multi-jurisdictional environment. This role provides leadership to a Payroll team of approximately 16 employees, including 1–2 direct reports, and is accountable for payroll accuracy and timeliness, regulatory compliance, tax administration, time and attendance, controls, reconciliations, audits, systems, projects, and operational excellence. The Manager also serves as the payroll project owner and subject‑matter expert for implementations, system changes, integrations, and process improvements, and leads the Payroll workstream for M&A activities in partnership with cross-functional teams.

Key Job Responsibilities

• Payroll Operations & Team Leadership
  • Lead day-to-day payroll operations for approximately 14,000 U.S. employees and 2,000 Canadian employees, including weekly U.S. and biweekly Canadian payrolls.
  • Ensure payrolls are accurate, timely, appropriately reviewed, reconciled, approved, and compliant with applicable requirements.
  • Provide leadership, coaching, workload prioritization, and direction to the Payroll team while establishing clear ownership, accountability, service expectations, and escalation protocols.
  • Review payroll results, exceptions, variances, and high-risk transactions and serve as a senior escalation point for complex payroll and employee pay matters.
  • Drive operational excellence through standardization, performance metrics, root-cause analysis, automation, effective controls, and continuous improvement.
• Payroll Regulatory Compliance, Wage & Hour & Pay Practices
  • Provide leadership and oversight of payroll regulatory compliance across the United States and Canada, including U.S. federal, state, and local and Canadian federal and provincial requirements, with specific expertise in California wage and hour compliance.
  • Apply strong knowledge of FLSA overtime and regular rate of pay requirements, including appropriate treatment of commissions, bonuses, incentives, premiums, and other variable compensation.
  • Oversee time and attendance and complex pay practices, including commission, incentive, productivity, flat-rate/flag-hour, guarantee, premium, bonus, and other variable compensation arrangements.
  • Monitor regulatory developments, assess payroll impacts, and partner with Legal, HR, Tax, Compensation, and Operations to implement required changes and mitigate compliance risk.
  • Identify compliance gaps and trends and lead corrective action, remediation, and sustainable process improvements.
• Payroll Tax, Controls & Audit
  • Oversee U.S. federal, state, and local and Canadian federal and provincial payroll tax administration, remittances, reconciliations, and regulatory reporting.
  • Ensure accurate quarterly and annual reconciliations and filings, including Forms 941, 940, W-2/W-3, applicable state/local withholding and unemployment filings, and Canadian T4/T4A, CPP/QPP, EI, income tax, and applicable provincial reporting.
  • Maintain a strong payroll control environment, including applicable SOX controls, approvals, reconciliations, segregation of duties, documentation, and audit readiness.
  • Lead and support internal and external payroll, tax, SOX, and wage and hour audits across U.S. and Canadian operations and ensure timely resolution and remediation of identified issues.
• Systems, M&A & Project Leadership
  • Provide operational ownership of payroll processes within Workday and ADP and ensure the accuracy and completeness of payroll-related data and integrations.
  • Serve as the payroll project owner and subject‑matter expert for implementations, system conversions and upgrades, integrations, enhancements, process transformation, and other strategic initiatives impacting payroll.
  • Lead the Payroll workstream for M&A activities, partnering with the broader M&A/project team to assess payroll requirements and coordinate system setup, data conversion, testing, reconciliation, and integration into ongoing payroll operations.
  • Lead payroll projects from planning through stabilization, including requirements, timelines, dependencies, risk assessment, configuration review, data validation, testing/UAT, parallel payrolls, cutover, go-live, and transition to ongoing operations.
  • Partner with HRIS, IT, Finance, Tax, Legal, HR, Compensation, Operations, and external vendors to align project priorities, requirements, dependencies, and deliverables.
  • Lead payroll technology, automation, and process improvement initiatives that strengthen operational excellence, scalability, compliance, controls, and employee experience while maintaining continuity of payroll operations.
• Process Governance & Business Partnership
  • Lead the creation, implementation, and ongoing maintenance of payroll standard operating procedures (SOPs), controls, process documentation, and business continuity procedures.
  • Ensure payroll processes and completed projects are transitioned into standardized, scalable, documented, and sustainable operations.
  • Partner effectively with HR, HRIS, Compensation, Benefits, Legal, Finance, Tax, IT, Operations, Internal Audit, and external vendors.

Education and/or Experience Required

• Bachelor’s degree and 4+ years of progressively responsible experience in payroll operations, payroll systems, implementations, or related disciplines within a complex, high-volume, multi-jurisdictional environment OR High school diploma and a minimum of 6+ years of progressively responsible experience in payroll operations, payroll systems, implementations, or related disciplines within a complex, high-volume, multi-jurisdictional environment.
• Minimum 1 year of payroll leadership experience with responsibility for a team of at least 10 employees, including a minimum of 2 direct reports.
• Demonstrated experience owning and leading complex, cross-functional payroll initiatives, including M&A, payroll implementations, system upgrades/conversions, integrations, process improvements, or enterprise system initiatives.
• Experience with payroll controls, quarterly and annual reconciliations and filings, SOX requirements, and internal/external payroll, tax, and wage-and-hour audits.
• Experience supporting payroll implementations, system upgrades, integrations, M&A, testing/UAT, and other cross-functional payroll initiatives.
• Experience with Workday and ADP strongly preferred.

Required Skills/Abilities

• Comprehensive understanding of U.S. federal, state, and local payroll taxation and wage and hour requirements, including FLSA regular rate of pay and overtime requirements, with specific expertise in California wage and hour compliance, as well as Canadian federal and provincial payroll requirements.
• Experience administering complex pay practices, including commission, incentive, productivity, flat-rate or job base pay, guarantee, premium, bonus, and other variable compensation arrangements.
• Proficiency with enterprise payroll and HRIS systems, with Workday and ADP experience preferred, and a strong understanding of complex payroll integrations, data flows, controls, reconciliations, and exception management.
• Demonstrated project leadership capability, with the ability to own and lead payroll initiatives from requirements and planning through testing, implementation, stabilization, and transition to ongoing operations.
• Proven ability to lead, coach, prioritize, and provide direction to a payroll team while simultaneously managing complex projects and critical payroll deadlines.
• Demonstrated analytical and problem-solving capabilities, including the ability to identify root causes, evaluate payroll, system, and compliance risks, and implement sustainable solutions.
• Proven ability to develop, implement, and maintain SOPs, controls, process documentation, and scalable practices that support operational excellence and continuous improvement.
• Effective communication, organizational, project management, and cross-functional leadership skills, with the ability to collaborate across HR, Finance, Legal, Tax, IT, Operations, and external partners.

Other Requirements

• Some travel may be required.