Senior Payroll Specialist – Canada

About Rippling

Rippling gives businesses one place to run HR, IT, and Finance. It brings together all of the workforce systems that are normally scattered across a company, like payroll, expenses, benefits, and computers. For the first time ever, you can manage and automate every part of the employee lifecycle in a single system.

Take onboarding, for example. With Rippling, you can hire a new employee anywhere in the world and set up their payroll, corporate card, computer, benefits, and even third-party apps like Slack and Microsoft 365—all within 90 seconds.

Based in San Francisco, CA, Rippling has raised $1.4B+ from the world’s top investors—including Kleiner Perkins, Founders Fund, Sequoia, Greenoaks, and Bedrock—and was named one of America's best startup employers by Forbes.

We prioritize candidate safety. Please be aware that all official communication will only be sent from @Rippling.com addresses.

About the role

We’re looking for a Senior Payroll Specialist to join Rippling’s Global Payroll Operations team and help lead payroll delivery for our EOR customers across Canada.

Our Global Payroll Operations team plays a critical role in ensuring the success of Rippling’s global payroll products, which are natively built and fully integrated with Rippling’s broader suite of products. This role sits at the center of Rippling’s global payroll operations, helping scale country-specific expertise, operational controls, and payroll excellence across our Canadian EOR business.

The Senior Payroll Specialist will own the most complex parts of the end-to-end payroll process, including escalations, corrections, off-cycle support, statutory payroll requirements, customer-facing payroll issues, and post-payroll resolution. Success in this role requires deep Canadian payroll knowledge, sharp judgment on tax and payroll treatment, and the ability to guide others through complex issues across pay types, earnings, deductions, reimbursements, allowances, statutory and leave-related payments, tax forms/TD1s, garnishments, terminations, Records of Employment (ROEs), and CRA or Revenu Québec-dependent cases.

This is a senior, highly cross-functional role for someone who can resolve high-complexity payroll issues, strengthen controls and documentation, coach payroll specialists, and partner with Product and Engineering on durable improvements to the EOR payroll experience.

What you will do

• Own complex EOR payroll processing for Canada, including inputs, approvals, corrections, off-cycle payments, statutory payroll outputs, post-payroll review, and issue resolution, and be accountable for accuracy, timeliness, and compliance.
• Act as the senior escalation point and trusted payroll and tax subject-matter expert for EOR customers across all provinces, responding directly to complex inquiries with clear, accurate, and timely guidance and owning resolution end to end, including overpayments, final pay, severance, bonuses, TD1/tax issues, statutory documents, ROEs, wage garnishments, EHT/provincial payroll taxes, workers’ compensation claims, and CRA/Revenu Québec disputes.
• Create, review, and validate pay types, payroll inputs, and payroll configurations, ensuring earnings, deductions, reimbursements, benefits, allowances, statutory payments, and leave-related pay receive the correct payroll and tax treatment in each jurisdiction.
• Advise customers and internal teams on Canadian payroll requirements, including federal and provincial income tax, CPP/QPP, EI/QPIP, pensions/RRSPs, taxable benefits, reimbursements, statutory deductions, and leave-related tax treatment, and interpret new or changing legislation for business impact.
• Lead payroll calendars, cutoffs, stakeholder readiness, and timelines to ensure on-time, accurate delivery across the region, anticipating risks and driving corrective action before customers are affected.
• Review, reconcile, and validate payroll outputs, including payslips, statutory remittances, correction calculations, and off-cycle calculations across federal and provincial jurisdictions, and serve as the primary liaison with CRA, Revenu Québec, and other agencies to resolve discrepancies.
• Lead year-end delivery, including T4/T4A and RL-1/RL-2 preparation, summaries, reconciliation, amendments, and customer and HR support through filing deadlines.
• Strengthen payroll controls, audit checks, quality-review processes, SOPs, escalation playbooks, customer guidance, knowledge articles, and product/process feedback loops to reduce repeat issues, improve consistency, mentor payroll specialists, and support scalable payroll operations.

What you will need

• Expert-level understanding of Canadian payroll and tax compliance, including federal and provincial income tax, CPP/QPP, EI/QPIP, CRA and Revenu Québec filings and remittances, ROE issuance, T4/T4A/RL-1 reporting, statutory pay, terminations, and year-end reconciliation.
• 5+ years of experience in Canadian payroll, payroll operations, payroll tax, or equivalent roles, ideally in a client-facing, EOR, or multi-customer environment
• Significant experience managing end-to-end payroll processing and complex escalations, including audits, notices, disputes, CRA/Revenu Québec queries, and customer-facing payroll issue resolution.
• Strong working knowledge of payroll tax treatment across pay types, payroll inputs, earnings, deductions, benefits, reimbursements, allowances, statutory payments, leave-related pay, and other payroll components, with strong judgment on when federal, provincial, pension, EI, and reporting treatment applies.
• Experience with EOR or multi-country payroll operations, including how payroll connects to contract terms, worker classification, and the client-employer-EOR relationship.
• Excellent communication, analytical, prioritization, documentation, mentoring, and quality-review skills, with the ability to manage complex payroll case queues and explain issues clearly
• Continuous-improvement mindset, strong attention to detail, and comfort working across operational systems, documentation tools, and case-management platforms; familiarity with Salesforce, JIRA, and Confluence is a plus.
• PCP (Payroll Compliance Professional) certification from the National Payroll Institute (NPI) is strongly preferred.
• C1 or C2 French language proficiency.

Additional Information

Rippling is an equal opportunity employer. We are committed to building a diverse and inclusive workforce and do not discriminate based on race, religion, color, national origin, ancestry, physical disability, mental disability, medical condition, genetic information, marital status, sex, gender, gender identity, gender expression, age, sexual orientation, veteran or military status, or any other legally protected characteristics, Rippling is committed to providing reasonable accommodations for candidates with disabilities who need assistance during the hiring process. To request a reasonable accommodation, please email [email protected]

Rippling highly values having employees working in-office to foster a collaborative work environment and company culture. For office-based employees (employees who live within a defined radius of a Rippling office), Rippling considers working in the office, at least three days a week under current policy, to be an essential function of the employee's role.

This role will receive a competitive salary + benefits. The salary for US-based employees will be aligned with one of the ranges below based on location; see which tier applies to your location here.

A variety of factors are considered when determining someone’s compensation–including a candidate’s professional background, experience, and location. Final offer amounts may vary from the amounts listed below.