Payroll Specialist in Toronto, Ontario at 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.

Equity compensation is complex. And doing it across international borders as an Employer of Record (EOR) is a whole new frontier. At Rippling, we enable companies to hire anywhere in the world. But when our customers grant stock options or RSUs to global team members, it triggers intricate tax, payroll, and compliance challenges. That’s where you come in.

As a Payroll Specialist on the EOR Equity Services team, you won't be managing cap tables or grant documentation. Instead, you'll be the technical mastermind who translates complex, global equity events into seamless, compliant payroll runs. No equity experience? No problem. If you bring strong multi-country payroll fundamentals, exceptional attention to detail, and a knack for problem-solving, we will teach you the equity domain.

• High Impact, Niche Domain: You aren't just pushing buttons on routine pay runs, you’re navigating the cutting edge of global EOR compliance.
• Bridge the Tech & Advisory Gap: You will be a trusted advisor to clients, a detective for edge cases, and a partner to our Engineering teams when software logic needs tweaking.
• Fast-Track Mastery: Equity is one of the most sought-after skill sets in tech payroll. This foundational role puts you at the intersection of international tax law, SaaS technology, and global equity.

Customer Advisory & Payroll Execution

• Guide Clients: Advise global customers on how to operationalize equity events—selecting earnings codes, handling taxable amounts, and setting up off-cycle pay runs.
• Process & Review: Ensure stock option exercises and RSU vestings flow through local payrolls accurately across multiple jurisdictions.
• Demystify the Complex: Clearly explain equity outcomes to clients and their employees (e.g., how imputed income works, why cash payouts don't always occur, and how tax withholding is calculated).

Compliance, Filings & Tech Collaboration

• Global Compliance: Support country-specific equity filings (e.g., UK ERS returns, Ireland RSS1, Australia ESS) alongside our filings specialists.
• Troubleshoot & Innovate: Partner with Engineering to flag logic errors, refine system workflows, and automate manual processes.
• Documentation & Process: Maintain SOPs, build internal cheat sheets, and make complex cross-border rules easy for the rest of the business to understand.

• 5+ Years in Payroll: Direct experience with payroll operations, tax compliance, or handling non-cash/imputed income (e.g., benefits-in-kind, relocation, fringe benefits). Multi-country payroll experience is a plus.
• Systems & Data Fluency: Comfort navigating case management tools (like Salesforce) and working with complex datasets in Excel/Sheets (VLOOKUPs, pivot tables, logic formulas).
• Communication Powerhouse: The ability to take dense, legalistic tax guidance and translate it into clear, simple instructions for clients.
• Technical Curiosity: Comfort collaborating with engineers to fix software bugs and improve internal systems.
• Adaptability: You thrive in fast-paced tech environments where processes evolve rapidly.

Bonus Points (Nice-to-Haves, Not Requirements):

• Direct experience processing US or international stock options (NSOs) and RSUs.

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 accommodations@rippling.com.

This role is open to fully remote for those located within British Columbia, and will require 1-3/days a week in office for those located in Ontario.

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This role will receive a competitive salary + benefits + bonus. 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.