Senior Payroll Tax Specialist (Fintech)

Location: Chicago, IL; Menlo Park, CA; or New York, NY, with in-person attendance expected at least 3 days per week.

Base pay: $100,000–$118,000 for Zone 1; $88,000–$104,000 for Zone 2; $78,000–$92,000 for Zone 3, plus bonus opportunities, equity, and benefits.

Company

Robinhood is a fintech company building financial products to democratize finance.

What you will do

• Own withholding tax configuration, mapping, maintenance, and sandbox testing in Workday with Corporate Engineering.
• Run payroll tax processing and reporting across weekly, bi-weekly, and international payroll cycles, including multi-state and internationally mobile employees.
• Reconcile payroll tax liabilities and verify payroll accuracy across US, Canadian, and global entities.
• Resolve legacy tax discrepancies, historical imbalances, GL payroll clearing variances, and escheatment requirements.
• Lead quarter-end and year-end execution, including W-2s, T4s, global equivalents, corrections, amended returns, and audit readiness.
• Manage agency notices, new tax account setups, external providers, and reporting for Finance, Accounting, Corporate Tax, and People Operations.

Requirements

• 8+ years of progressive, hands-on payroll tax experience across US and Canadian payroll; international experience is a plus.
• Hands-on experience configuring and maintaining payroll tax rules in an enterprise ERP; Workday Payroll preferred.
• Experience with third-party tax filing providers such as ADP SmartCompliance.
• Strong understanding of payroll tax liability reconciliation, quarter-end and year-end filings, corrections, and amendments.
• Advanced Excel skills for data analysis and reconciliations, plus comfort using AI tools to streamline reconciliations and filings.
• Analytical ability to resolve ambiguous tax scenarios with limited guidance.
• Experience holding vendors accountable and collaborating across Engineering, Finance, and Tax.

Nice to have

• Certified Payroll Professional (CPP).
• Bachelor’s degree in Finance, Accounting, Taxation, or a related field, or equivalent practical experience.

Culture & Benefits

• High-impact work within a fast-moving, ethics-focused environment.
• Performance-driven compensation with bonus programs, equity ownership, and 401(k) matching.
• Health, life, disability, fertility, mental health, paid time off, sick time, parental leave, and company holiday benefits.
• Flexible lifestyle wallet for wellness, learning, and other expenses.
• US employees may access the Robinhood Employee Fund; office locations offer catered meals, events, and comfortable workspaces.
• AI tools and continuous AI skill-building are available to all employees.