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.