Senior Payroll Specialist

About the Role
We are seeking an experienced and detail-oriented Senior Payroll Specialist (IC3) to take end-to-end ownership of our multi-state US and Canadian payroll operations.
We are in the middle of an exciting AI transformation, actively embedding AI into everything we do. In this role, you will lead the accurate, compliant, and timely processing of payroll for a growing workforce while directly contributing to how we re-imagine payroll operations using modern AI and automation tools. This role exercises independent judgment while managing complex payroll operations, identifying operational risks, and recommending practical solutions that support payroll accuracy, compliance, and continuous process improvement.
As a senior individual contributor, you will act as a trusted SME for employee payroll inquiries, lead complex tax and regulatory compliance projects across US states and Canadian provinces, and help drive the future of AI-powered payroll systems and workflows.
Payroll Environment
Supports 850+ employees across three legal entities in the United States and Canada.
Processes two separate U.S. bi-weekly payrolls utilizing ADP Workforce Now (WFN).
Processes Canadian semi-monthly payroll utilizing UKG Payroll for employees located in Ontario and British Columbia.
Workday serves as the HR System of Record (HRIS) supporting employee lifecycle events, organizational changes, compensation updates, and payroll-related employee data.
Partners closely with Human Resources, Benefits, Finance, Accounting, Treasury, and other key stakeholders to ensure accurate, timely, and compliant payroll operations.
What you will do:

• Payroll Processing & Operations (US & Canada)
• Lead end-to-end processing of semi-monthly / bi-weekly payrolls for US and Canada employees (exempt, non-exempt, hourly, and salary).
• Process complex payments, including equity (NSO/ISO/RSU tax withholding), bonuses, commissions, retro pay, terminations, severance, and off-cycle runs.
• Partner with Service Delivery to process hires, transfers, compensation adjustments, leaves of absence (FMLA, STD, LTD, Canadian EI/MAT leaves), and terminations.
• Calculate and ensure accurate processing of statutory deductions, garnishments, court orders, 401(k)/RRSP contributions, and benefit withholdings.

Compliance & Tax Management

• Ensure strict compliance with US federal, state, and local payroll tax laws, FLSA overtime regulations, and labor standards.
• Oversee Canadian payroll compliance across multiple provinces (Ontario & British Columbia), including Employment Insurance (EI), Canada Pension Plan (CPP/QPP), Employer Health Tax (EHT/CNESST), and Record of Employment (ROE) issuance.
• Partner with external payroll vendors and tax accountants to manage quarter-end and year-end processes, including US W-2/1095-C auditing and Canadian T4/T4A/RL-1 filings.
• Support internal and external payroll, benefit, and financial audits (e.g., 401(k) audits, workers' comp, tax authority notices).
• Process Improvement & Systems
• Identify opportunities to automate, streamline, and scale payroll processes between 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 in partnership with the Finance/Accounting team.
• Employee Experience & Collaboration
• Serve as the primary point of contact for employee inquiries regarding paychecks, withholdings, tax forms, and deductions, delivering high-touch, empathetic support
• Maintain comprehensive documentation for payroll processes, standard operating procedures (SOPs), and compliance controls.

Qualifications & Requirements

• Experience: 5+ years of hands-on experience independently running both US and Canadian payrolls in high-growth or mid-to-large multi-state/multi-province environments.
• Deep expertise in US payroll tax mechanics (multi-state withholding, FLSA rules, fringe benefits).
• Strong working knowledge of Canadian payroll mechanics, provincial employment standards, ROE processing).
• Proficiency with ADP Workforce Now, UKG Payroll, and Workday, with the ability to navigate employee lifecycle transactions and payroll processing across integrated payroll and HR systems.
• Intermediate to Advanced Microsoft Excel skills with experience analyzing, reconciling, auditing, and validating large payroll datasets.
• AI & Process Modernization: Strong "AI-first" mindset with experience leveraging generative AI and automation tools to optimize multi-country payroll workflows, draft employee communications, and accelerate complex tax/compliance research.
• Demonstrated ability to independently research payroll issues, evaluate options, exercise sound judgment, and recommend practical solutions while maintaining strict confidentiality.
• Exceptional accuracy, attention to detail, sound judgment, high integrity when handling confidential compensation data, strong organizational and time management skills, and excellent written and verbal communication skills.

Certifications (Preferred):

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

Visa sponsorship is not offered for this role.