Payroll Leader

Summary

Join Wealthsimple as our Payroll Leader and oversee payroll operations for our Canadian and US employees. You will lead a team of payroll specialists, ensuring accurate and timely payroll processing while maintaining compliance with all regulations. This role requires deep expertise in payroll management, system optimization, and a passion for seamless employee experiences. You will develop and implement protocols to enhance employee support and satisfaction, manage payroll systems, and lead payroll-related projects. The ideal candidate will have extensive experience in multi-country payroll management and a strong understanding of Canadian and US payroll regulations. This is a leadership position within a rapidly growing fintech company.

Requirements

• 8+ years of experience in payroll management, with at least 3 years in a leadership role
• Proven expertise in managing payroll operations for a multi-country workforce
• In-depth knowledge of payroll regulations, compliance, and tax reporting requirements in Canada and the US (experience with other regions is a plus)
• Experience with payroll platforms such as ADP, Workday, Gusto and Deel
• Strong analytical skills with a keen eye for detail and accuracy
• Demonstrated ability to lead audits, reconciliations, and year-end payroll processes
• Exceptional problem-solving skills and ability to manage complex payroll issues
• Strong communication and interpersonal skills, with a focus on collaboration and employee experience
• Ability to manage multiple priorities and meet tight deadlines in a fast-paced environment

Responsibilities

• Lead a team of payroll specialists who support day to day processing of payroll processes and act as the approver of all payrolls
• Develop and implement protocols to enhance employee support and satisfaction with payroll services
• Oversee end-to-end payroll processing for all employees, ensuring timely and accurate payments
• Manage Canadian and US payroll operations, including integration with external platforms like Deel for international workforce management
• Coordinate payroll schedules and deadlines with internal and external stakeholders to ensure timely and accurate payroll processing
• Oversee the management and process improvement of both semi-monthly and bi-weekly payroll cycles
• Ensure payroll compliance with local, federal, and international regulations
• Manage tax withholding, remittance, and reporting processes in all relevant jurisdictions
• Stay updated on legislative changes affecting payroll and implement necessary adjustments
• Lead payroll reconciliations to ensure data integrity and accuracy across systems
• Prepare payroll data and documentation for internal and external audits
• Manage year-end processes, including issuance of tax forms (e.g., T4s, T2200s, etc.) and reconciling annual payroll records
• Oversee payroll system functionality, ensuring it meets the organization’s needs
• Business lead for system updates, enhancements, and integrations with other HR or finance systems
• Partner with HRIS and external vendors to troubleshoot and resolve system issues
• Generate and analyze payroll reports for internal stakeholders, including Finance and HR teams
• Provide insights and recommendations based on payroll data to inform decision-making
• Drive payroll-related projects, such as process improvements, system migrations, and policy updates
• Collaborate on cross-functional initiatives that involve payroll considerations
• Support business expansion efforts by establishing payroll operations in new regions

Preferred Qualifications

Payroll certifications (e.g., PCP) are an asset

Benefits

• Competitive salary with top-tier health benefits and life insurance
• Retirement savings matching plan using Wealthsimple Work
• 20 vacation days per year and unlimited sick and mental health days
• Up to $1,500 per year towards wellness and professional development budgets respectively
• 90 days away program: Employees can work internationally in eligible countries for up to 90 days per calendar year
• A wide variety of peer and company-led Employee Resource Groups (ie. Rainbow, Women of Wealthsimple, Black @ WS)
• Company-wide wellness days off scheduled throughout the year