Senior Tax and Compliance Analyst (Payroll)

This position is needed to lead payroll tax compliance and regulatory adherence across multiple regions, ensuring risk mitigation and operational efficiency for a global, mobile workforce.

We are looking for a Senior Tax and Compliance Analyst to oversee payroll tax compliance and mobility regulations across the US, Canada, and LATAM. This role requires expert knowledge of complex tax laws and social security frameworks to manage a highly mobile, fast-growing tech workforce. Reporting to the Senior Manager Americas Payroll, you will drive risk mitigation, compliance accuracy, and scalable process improvements within a dynamic multinational environment.

• Manage all payroll tax compliance, filings, and reconciliations across the US, Canada, and LATAM.
• Monitor employee movement across US states and international borders to ensure accurate tax withholding.
• Evaluate corporate tax footprint implications resulting from remote worker locations.
• Ensure correct application of local social security taxes and international totalization agreements.
• Track changing tax laws, statutory rates, and local compliance requirements in all active jurisdictions.
• Act as the primary point of contact for tax authorities, external auditors, and local payroll partners.
• Lead year-end tax reporting processes, including US W-2s, Canadian T4s, and local LATAM statutory filings.
• Build scalable internal workflows to automate tax adjustments for mobile employees.

• 6+ years of payroll tax and compliance experience, ideally within a high-growth technology company.
• Proven expertise in US federal, state, and local taxes, as well as Canadian provincial taxes.
• Advanced knowledge of multi-state taxation, trailing liabilities, and cross-border remote work risks.
• Proficiency with global payroll platforms (e.g., Workday, One Source Virtual, ADP, Deel, etc).
• Exceptional ability to translate complex statutory tax laws into clear, actionable corporate policies.

Nice to have

• Expertise in LATAM payroll regulations (e.g., Brazil, Mexico, Colombia).
• Certified Payroll Professional (CPP) or equivalent international certification.
• Experience navigating compliance for equity compensation (RSUs, stock options) across multiple tax jurisdictions.

• Working at Twilio offers many benefits, including competitive pay, generous time off, ample parental and wellness leave, healthcare, a retirement savings program, and much more. Offerings vary by location.