Senior Payroll Tax Specialist

Robinhood•Chicago, IL

12d•$78,000 - $118,000•Hybrid

About The Position

Robinhood is seeking a Senior Payroll Tax Specialist to help build its global payroll ecosystem. Reporting to the Sr. Manager, Global Payroll, this role serves as the internal payroll tax subject matter expert and primary operational contact for external providers. The specialist owns payroll tax processing and reporting across US, Canadian, and global entities, ensuring compliance with local, state, federal, and international regulations. Responsibilities include configuring and testing withholding tax setups in Workday, reconciling liabilities, leading quarter-end and year-end activities, and preparing for audits. Early priorities include resolving legacy tax account discrepancies and establishing scalable reconciliation processes. The role also partners with Finance, Engineering, Accounting, Corporate Tax, and People teams to provide accurate reporting and analysis. The role is based in Robinhood's Chicago, Illinois; Menlo Park, California; or New York, New York offices. In-person attendance is expected at least three days per week.

Requirements

At least 8 years of progressive, hands-on payroll tax experience across US 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, and corrections and amendments.
Advanced Excel skills for data analysis and reconciliations.
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 tax configuration 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.
Support payroll transitions resulting from M&A activity.
Verify payroll accuracy through parallel reconciliations after each payroll.
Reconcile payroll tax liabilities weekly across US, Canadian, and global entities, and reconcile quarterly returns filed by third-party providers.
Resolve legacy tax discrepancies and historical imbalances, including GL payroll clearing account variances and unclaimed payroll check (escheatment) requirements.
Lead quarter-end and year-end execution, including W-2s, T4s, 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 payroll and tax providers and hold vendors accountable.
Deliver reporting and liability analysis to Finance, Accounting, Corporate Tax, and People Operations.

Benefits

Performance-driven compensation with multipliers for outsized impact.
Bonus programs and equity ownership.
401(k) matching.
100% paid health insurance for employees, with 90% coverage for dependents.
Access for eligible US employees to the Robinhood Employee Fund, which provides exposure to Robinhood Ventures funds.
Access to AI tools and continuous AI skill-building.
Lifestyle wallet: a flexible benefits spending account for wellness, learning, and more.
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.