Senior Payroll Specialist

Payroll Processing & Operations (US & Canada)

• Lead end-to-end semi-monthly and bi-weekly payroll processing for US and Canadian employees, including exempt, non-exempt, hourly, and salaried workers.
• Process complex payments, including equity tax withholding for NSOs, ISOs, and RSUs; bonuses; commissions; retroactive pay; terminations; severance; and off-cycle runs.
• Partner with Service Delivery on hires, transfers, compensation adjustments, leaves of absence, and terminations.
• Calculate and process statutory deductions, garnishments, court orders, 401(k) and RRSP contributions, and benefit withholdings.

Compliance & Tax Management

• Ensure compliance with US federal, state, and local payroll tax laws, FLSA overtime regulations, and labor standards.
• Manage Canadian payroll compliance across Ontario and British Columbia, including EI, CPP/QPP, EHT/CNESST, and ROE issuance.
• Partner with external payroll vendors and tax accountants on quarter-end and year-end processes, including US W-2/1095-C auditing and Canadian T4, T4A, and RL-1 filings.
• Support internal and external payroll, benefits, and financial audits, including 401(k), workers' compensation, and tax authority notice audits.

Process Improvement & Systems

• Identify opportunities to automate, streamline, and scale payroll processes across HRIS, time-tracking, and accounting systems.
• Audit payroll inputs and outputs systematically to maintain a near-zero error rate.
• Reconcile payroll tax accounts and ledger entries with Finance and Accounting.
• Leverage generative AI and automation tools to optimize multi-country payroll workflows, draft employee communications, and accelerate tax and compliance research.

Employee Experience & Collaboration

• Serve as the primary contact for employee inquiries about paychecks, withholdings, tax forms, and deductions.
• Maintain comprehensive payroll process documentation, standard operating procedures, and compliance controls.
• Work cross-functionally with Human Resources, Benefits, Finance, Accounting, Treasury, and other stakeholders.

Requirements

• 5+ years of hands-on experience independently running both US and Canadian payroll in high-growth or mid-to-large multi-state and multi-province environments.
• Deep expertise in US payroll tax mechanics, including multi-state withholding, FLSA rules, and fringe benefits.
• Strong knowledge of Canadian payroll mechanics, provincial employment standards, and ROE processing.
• Proficiency with ADP Workforce Now, UKG Payroll, and Workday.
• Intermediate to advanced Microsoft Excel skills, including analysis, reconciliation, auditing, and validation of large payroll datasets.
• AI-first mindset and experience using generative AI and automation tools for process optimization.
• Ability to research payroll issues independently, evaluate options, exercise sound judgment, and recommend practical solutions while maintaining confidentiality.
• Exceptional accuracy, attention to detail, integrity, organization, time management, and written and verbal communication skills.

Preferred Certifications

• Certified Payroll Professional (CPP) or Fundamental Payroll Certification (FPC).
• Payroll Compliance Professional (PCP) via the National Payroll Institute.

Compensation & Benefits

• Full-time employees receive Restricted Stock Units and merit-based refresh grants.
• 24 weeks of fully paid parental leave for primary carers and 12 weeks for supporting carers.
• Unlimited PTO in applicable regions and generous PTO globally.
• Flexible hybrid work model.
• Learning, mentorship, well-being, mental health, volunteering, and inclusion programs.