Payroll Execution:Oversee day-to-day payroll administration and processing, acting as an advisor to People & Culture Leads for life cycle events with complex payroll implications.
Take full accountability for overall payroll compliance and accuracy, validating all inputs and outputs across Canada, USA, UK, Chile, and EoR ahead of each cycle.
Provide backup payroll processing coverage to ensure uninterrupted, on-time payroll.
Monitor and improve data quality and speed when generating new employee profiles to seamlessly trigger the HRIS onboarding processes.
Partner with Finance to perform monthly general ledger reconciliations and ensure accurate accruals and cost forecasting for payroll and benefits-related expenses.
Total Rewards & BenefitsServe as a subject matter expert across the global advantages programs (Canada, USA, UK, EoR), interfacing with benefits brokers, managing renewal dates, producing regular reporting and executing reconciliation processes.
Manage employee health benefits and retirement plan administration.
Collaborate with People & Culture Leads to initiate, manage, and track leave of absences, aligned to global policy and compliance requirements.
Support recurring pay equity analysis in partnership with the People Operations Lead.
HRIS & Systems Administration:Manage the day-to-day relationship with Deel, holding the vendor accountable for product enhancements and support levels.
Monitor day-to-day HiBob and Deel administration performed by People Operations Specialists, including regular data quality audits and ongoing system integrity monitoring.
Design and build HiBob and Deel workflow enhancements,



administer complex edge-case scenarios, and leverage system data to deliver actionable Business Insights to leadership.using Claude) that streamline payroll, benefits, and HRIS processes, reduce manual effort, and improve data accuracy.
Analytics & InsightsOwn the development and tracking of key People & Culture metrics, creating dashboards and data models that translate raw HRIS data into strategic analytics and insights for the global team.7+ years of progressive experience in Payroll and People Operations, with at least 3+ years at a lead level within a fast-growing, global organization.
Experience with Canada and USA payroll (UK and Chilean experience an asset).
Proven track record of managing and supporting finance and payroll audits, ensuring accurate general ledger reconciliations and full audit readiness.
Proven experience administering payroll and total rewards across the employee lifecycle for a global employee base (compliance, benefits, and leave management).
High-ownership mentality with the ability to evaluate business opportunities and risks to make sound decisions independently and communicate to stakeholders.
Workday, Rippling, BambooHR), including building complex workflows and automations.
Advanced proficiency with spreadsheets (VLOOKUPs, Pivot Tables, Index/Match) with experience translating raw HR data into dashboards and executive insights (Google Sheets preferred).
Experience managing sensitive payroll escalations or complex leave/benefits cases with empathy and discretion.
Fluent in Spanish an asset.
Familiarity with employer of record models and tools like Deel, Remote, or Oyster.

📌 Payroll & Rewards Operations Lead (Winnipeg)
🏢 Apply Digital
📍 Winnipeg