Senior Payroll Tax Specialist

About the team + role

We are building an elite team, applying frontier technologies to the world's biggest financial problems. We're looking for bold thinkers. Sharp problem-solvers. Builders who are wired to make an impact. Robinhood isn't a place for complacency, it's where ambitious people do the best work of their careers. We're a high-performing, fast-moving team with ethics at the center of everything we do. Expectations are high, and so are the rewards.

Our Global Payroll team is at the foundational stage of building a world-class global payroll ecosystem, and it's a great time to join! We partner closely with Corporate Tax, Corporate Engineering, Accounting, Benefits, Legal, and Global Mobility to make sure employees are paid accurately and on time. We build systems and processes that scale across weekly, bi-weekly, and international payroll cycles. We also work hand in hand with external payroll and tax providers, and we expect strong accountability on both sides. Ethics and accuracy sit at the center of how we work.

As a Senior Payroll Tax Specialist, you will report to the Sr. Manager, Global Payroll and serve as the internal subject matter expert and primary operational contact for our external providers. You will own payroll tax processing and reporting across US, Canadian, and global entities, keeping us compliant with local, state, federal, and international regulations. You will configure and test withholding tax setups in Workday, reconcile liabilities, and lead quarter-end, year-end, and audit readiness. An early focus will be resolving legacy tax account discrepancies and putting in place the reconciliation foundation we need to scale, so your work will shape how this function runs for years to come! You will also partner with teams across Finance, Engineering, and People to deliver accurate reporting and analysis.

This role is based in our Chicago, IL, Menlo Park, CA and New York, NY offices, with in-person attendance expected at least 3 days per week.

What you'll do

• Own withholding tax configuration in Workday, including setup, mapping, and maintenance of state, local, and international tax tables, and partner with Corporate Engineering to test changes in sandbox before production release.
• Run payroll tax processing and reporting across weekly, bi-weekly, and international payroll cycles, including multi-state and internationally mobile employees, and support payroll transitions from M&A activity.
• Verify accuracy after each payroll with parallel reconciliations, and reconcile payroll tax liabilities weekly across US, Canadian, and global entities, along with quarterly returns filed by third-party providers.
• Resolve and permanently close out 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, and global equivalents, plus corrections and amended returns (W-2C, Form 941-X), and prepare for payroll tax audits with the IRS, CRA, HMRC, and state and local authorities.
• Manage agency notices and new tax account setups, act as the point of contact for third-party providers, and deliver reporting and liability analysis to Finance, Accounting, Corporate Tax, and People Operations.

What you bring

• 8+ years of progressive, hands-on payroll tax experience across US and Canadian payroll, with international experience a plus.
• Hands-on experience configuring and maintaining payroll tax rules in an enterprise ERP (Workday Payroll preferred) and working with third-party tax filing providers such as ADP SmartCompliance.
• Solid understanding of payroll tax reconciliation, including liability reconciliation, quarter-end and year-end filings, and corrections and amendments.
• Advanced Excel skills for data analysis and reconciliations, plus comfort using AI tools to streamline reconciliations and filings.
• An analytical approach to untangling ambiguous tax scenarios with limited guidance.
• Experience holding vendors accountable and collaborating across Engineering, Finance, and Tax teams.
• Bonus: Certified Payroll Professional (CPP) and a bachelor's degree in Finance, Accounting, Taxation, or a related field (or equivalent practical experience).

What we offer

• Challenging, high-impact work to grow your career
• Performance driven compensation with multipliers for outsized impact, bonus programs, equity ownership, and 401(k) matching
• Top Tier benefits to fuel your work, including 100% paid health insurance for employees with 90% coverage for dependents
• Access to the Robinhood Employee Fund that gives eligible US employees the opportunity to invest in a private employee fund that provides exposure to Robinhood Ventures funds.
• Access to the best AI tools on the market and continuous AI skill-building for every employee, technical or not.
• Lifestyle wallet - a highly flexible benefits spending account for wellness, learning, and more
• Employer-paid life & disability insurance, fertility benefits, and mental health benefits
• Time off to recharge including company holidays, paid time off, sick time, parental leave, and more!
• Exceptional office experience with catered meals, events, and comfortable workspaces.