Senior Payroll Tax Specialist

Robinhood • Chicago, NY

11d • Onsite

About The Position

Robinhood is building a global payroll ecosystem that supports weekly, bi-weekly, and international payroll cycles. The Senior Payroll Tax Specialist reports to the Sr. Manager, Global Payroll and serves as the internal payroll tax subject matter expert and primary operational contact for external providers. The role owns payroll tax processing and reporting across U.S., Canadian, and global entities, maintaining compliance with local, state, federal, and international regulations. An early priority is resolving legacy tax account discrepancies and establishing scalable reconciliation processes. The position partners with Corporate Tax, Corporate Engineering, Accounting, Benefits, Legal, Global Mobility, Finance, and People teams to support accurate payroll, reporting, and analysis.

The role is based in the Chicago, Illinois; Menlo Park, California; or New York, New York offices, with in-person attendance expected at least three days per week.

Requirements

• At least 8 years of progressive, hands-on payroll tax experience across U.S. and Canadian payroll.
• Hands-on experience configuring and maintaining payroll tax rules in an enterprise ERP.
• Experience with payroll tax reconciliation, including liability reconciliation, quarter-end and year-end filings, corrections, and amendments.
• Advanced Excel skills for data analysis and reconciliations, and comfort using AI tools to streamline reconciliations and filings.
• An analytical approach to resolving ambiguous tax scenarios with limited guidance.
• Experience holding vendors accountable and collaborating across Engineering, Finance, and Tax teams.

Nice To Haves

• International payroll tax experience.
• Workday Payroll experience.
• Experience working with third-party tax filing providers such as ADP SmartCompliance.
• Certified Payroll Professional (CPP) certification.
• A bachelor's degree in Finance, Accounting, Taxation, or a related field, or equivalent practical experience.

Responsibilities

• Own withholding tax configuration in Workday, including setup, mapping, and maintenance of state, local, and international tax tables; partner with Corporate Engineering to test changes in a sandbox before production release.
• Run payroll tax processing and reporting across weekly, bi-weekly, and international payroll cycles, including for multi-state and internationally mobile employees, and support payroll transitions resulting from M&A activity.
• Verify payroll accuracy after each cycle through parallel reconciliations, and reconcile payroll tax liabilities weekly across U.S., Canadian, and global entities, as well as quarterly returns filed by third-party providers.
• Resolve and permanently close legacy tax discrepancies and historical imbalances, including general ledger payroll clearing account variances and unclaimed payroll check (escheatment) requirements.
• Lead quarter-end and year-end execution, including W-2s, T4s, and global equivalents, corrections, and amended returns such as W-2C and Form 941-X.
• Prepare for payroll tax audits with the IRS, CRA, HMRC, and state and local authorities.
• Manage agency notices and new tax account setups, serve as the point of contact for third-party providers, and provide reporting and liability analysis to Finance, Accounting, Corporate Tax, and People Operations.

Benefits

• Performance-driven compensation, bonus programs, equity ownership, and 401(k) matching.
• 100% paid health insurance for employees and 90% coverage for dependents.
• Access for eligible U.S. employees to the Robinhood Employee Fund, which provides exposure to Robinhood Ventures funds.
• Access to AI tools and continuous AI skill-building.
• Lifestyle wallet for wellness, learning, and other spending.
• Employer-paid life and disability insurance, fertility benefits, and mental health benefits.
• Company holidays, paid time off, sick time, parental leave, and more.
• Catered meals, events, and comfortable workspaces.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed