Senior Payroll Specialist

Accountabilities:

• Own and oversee full-cycle payroll processing for a diverse portfolio of Canadian clients across weekly, bi-weekly, semi-monthly, and monthly payroll cycles.
• Manage complex payroll transactions including new hires, compensation changes, terminations and ROEs, taxable benefits, statutory holiday pay, commissions, deductions, EHT, WSIB, RRSPs, and other payroll adjustments.
• Review payroll calculations, reconciliations, remittances, filings, and year-end reporting, including T4 and T4A information slips.
• Maintain strong oversight of Canadian federal and provincial payroll compliance, proactively identifying risks related to accuracy, deadlines, legislation, and service delivery.
• Act as a senior escalation point for complex payroll questions, discrepancies, CRA matters, government registrations, and other payroll-related issues.
• Build trusted client relationships by providing clear, proactive guidance on payroll, compliance requirements, process improvements, and emerging issues.
• Take ownership of client concerns from identification through resolution, maintaining timely communication and a high-quality client experience.
• Perform detailed payroll reviews and audits to identify discrepancies, strengthen controls, and prevent recurring issues.
• Use cloud-based tools such as Wagepoint and Karbon to improve payroll accuracy, visibility, efficiency, and communication, while identifying opportunities for automation.
• Identify root causes of payroll issues and lead sustainable improvements to workflows, controls, documentation, and standardized procedures.
• Develop and maintain payroll SOPs, checklists, training resources, and step-by-step procedures to support consistency and scalability.
• Serve as a payroll subject-matter resource for Cloud Accountants and other team members by providing guidance, coaching, and support on complex matters.
• Research changes to payroll legislation, CRA guidance, and industry practices, proactively communicating relevant updates and recommendations to colleagues and clients.
• Collaborate with payroll and finance leadership on initiatives that improve service quality, team capabilities, and the overall payroll offering.

Requirements

• 4–5+ years of progressive full-cycle Canadian payroll experience, ideally supporting multiple businesses or clients simultaneously.
• Demonstrated ability to independently manage complex payroll portfolios, resolve escalated issues, and exercise sound judgment in payroll and compliance matters.
• Strong understanding of Canadian federal and provincial payroll legislation, tax requirements, remittances, year-end reporting, and government filings.
• Canadian Payroll Compliance Practitioner (PCP) designation is an asset; additional payroll certifications or related accounting credentials are also considered an asset.
• Exceptional attention to detail, accuracy, and analytical ability, with a proactive approach to identifying and resolving discrepancies.
• Strong experience with payroll software and cloud-based systems, combined with an interest in automation, reporting, and technology-enabled process improvement.
• Proven ability to build credibility and trust with clients and communicate complex payroll matters clearly and confidently.
• Strong organizational skills and the ability to manage multiple priorities, clients, and relationships simultaneously.
• Comfortable acting as a senior resource for colleagues, sharing knowledge, providing guidance, and supporting team development.
• Proactive, solutions-oriented, and capable of working independently with limited supervision while recognizing when escalation is appropriate.
• Excellent written and verbal communication skills, with the ability to collaborate effectively with clients, colleagues, and leadership.
• High level of professionalism, discretion, integrity, and confidentiality when handling sensitive payroll and employee information.
• Commitment to staying current with payroll legislation, CRA guidance, technology, and evolving industry practices.
• Entrepreneurial mindset with a willingness to take initiative, improve processes, and contribute to the growth and evolution of the service offering.
• Must be based in Canada and eligible to work in Canada.

Benefits

• $75,000–$80,000 annual compensation.
• Competitive compensation and bonus structure.
• Fully remote work from anywhere in Canada.
• Flexible working hours with a results-focused approach rather than measuring performance by hours worked.
• Half-day Fridays during August.
• Career advancement and growth opportunities within a rapidly expanding organization.
• Comprehensive benefits package.
• $500 annual training allowance.
• Hardware and software provided to support effective remote work.
• $250 contribution toward home office setup.
• Ongoing coaching and mentorship from experienced leadership.
• Exposure to modern cloud-based technologies and opportunities to explore new platforms.
• Opportunity to work with a diverse range of Canadian businesses, entrepreneurs, non-profit organizations, and high-growth companies.
• Collaborative, inclusive, entrepreneurial environment with significant autonomy and visibility.