Director, Global Tax Information, Reporting & Withholding

You will lead customer and payee tax reporting, documentation, and withholding across Square, Cash App, Afterpay, and other Block businesses. You will also lead the team and providers, embed requirements in products and onboarding, modernize operations to improve compliance and customer experience.

Responsibilities:

• Own global reporting and withholding strategy, governance, and implementation of regulatory changes.
• Own Forms 1099 and 1042-S, including filing, recipient delivery, reconciliations, and corrections. Lead digital asset reporting, including applicable cost basis and transfer-reporting requirements.
• Own backup and foreign-person withholding, including under Chapters 3 and 4, state obligations, deposits, reconciliations, and Forms 945 and 1042.
• Lead applicable FATCA, Form 8966, CRS, DAC7, Australian and other local reporting.
• Partner with Product, Engineering, and Data to build and test documentation, reportability, withholding, and reporting logic.
• Lead notices, B-Notice processes, examinations, and penalty defense.
• Own reporting and withholding controls; coordinate SOX requirements with Tax Reporting and Internal Audit.
• Develop the team and manage platforms and providers.
• Deliver an automation roadmap with Tax Technology and Engineering.

Requirements:

• 10+ years of information reporting and withholding experience.
• Bachelor's degree in Accounting, Finance, or a related field.
• Deep 1099, Chapters 3 and 4, FATCA, and CRS expertise.
• Experience translating tax requirements into tested product specifications.
• Experience rebuilding high-volume workflows and delivering measurable improvements through automation or AI.
• People leadership and clear communication of reporting risk.

Preferred Qualifications:

• Form 1099-DA or other digital asset reporting implementation.
• Platform implementation or migration, high-volume corrections, and coordination with Support, Legal, and Compliance.