Payroll Leader

Your career is an investment that grows over time!

Wealthsimple is on a mission to help everyone achieve financial freedom by reimagining what it means to manage your money. Using smart technology, we take financial services that are often confusing, opaque and expensive and make them transparent and low-cost for everyone. We’re the largest fintech company in Canada, with over 4 million users who trust us with more than $50 billion in assets.

Our teams ship often and make an impact with groundbreaking ideas. We're looking for talented people who keep it simple and value collaboration and humility as we continue to create inclusive and high-performing teams where people can be inspired to do their best work.

Wealthsimple is seeking a Payroll Leader to oversee our payroll operations and ensure accurate, compliant, and timely payroll processing across our Canada and US based employees. We are looking for a dynamic professional who is comfortable in a rapidly growing organization and has the ability to navigate challenging payroll projects with ease. Reporting to the leader of HRIS and Payroll, you will lead payroll execution, provide strategic direction for payroll systems, and support our growing workforce. The ideal candidate will have deep expertise in payroll management, compliance, and system optimization, as well as a passion for fostering seamless processes and employee experiences.

As the Payroll Leader, you will:

• 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
  
  
  

Compliance & Tax Reporting:

• 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
  
  
  

Payroll Systems:

• 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
  
  
  

Ad Hoc Projects:

• 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
  
  
  

What you bring:

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

Why Wealthsimple?

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

We’re a remote-first team, with over 1,000 employees coast to coast in North America. Be a part of our Canadian success story and help shape the financial future of millions — join us!

Read our Culture Manual and learn more about how we work.

DEI Statement

At Wealthsimple, we are building products for a diverse world and we need a diverse team to do that successfully. We strongly encourage applications from everyone regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.

Accessibility Statement

Wealthsimple provides an accessible candidate experience. If you need any accommodations or adjustments throughout the interview process and beyond, please let us know, and we will work with you to provide the necessary support and make reasonable accommodations to facilitate your participation. We are continuously working to improve our accessibility practices and welcome any feedback or suggestions on how we can better accommodate candidates with accessibility needs.