Director, Tax Reporting and Cost Basis

Your Role

As Director, Tax Reporting & Cost Basis, you will define and lead Alpaca’s global tax reporting strategy, with a U.S.-first foundation and expanding international complexity. You will own the end-to-end design, build, and execution of a proprietary cost basis engine and scalable tax reporting infrastructure. This includes ensuring accurate, timely, and compliant reporting across regimes such as 1099, 1042-S, 5498, and contribution-related reporting, while building frameworks to support global clients.

Your mandate is to deliver a clean, accurate, and on-time tax season every January, supported by rigorous processes, repeatable playbooks, and proactive system validation throughout the year.

Things You Get to Do

• Define and execute Alpaca’s global tax reporting strategy, balancing U.S. requirements with international client needs
• Architect and lead the build of a proprietary cost basis engine from the ground up, in close partnership with Engineering
• Design and implement a global tax matrix (country of residence vs. security domicile) to determine treaty rates and withholding logic
• Oversee all reporting obligations including 1099, 1042-S (non-U.S. persons), 5498 (retirement accounts), and contribution-related reporting
• Establish a year-round tax readiness program, including multiple test cycles, reconciliations, and “dry runs” to validate systems and data pipelines
• Own delivery of a flawless January tax season, with clear guidelines, SLAs, and operational rubrics for execution
• Build and scale a high-performing team, setting standards for accuracy, accountability, and continuous improvement
• Partner cross-functionally with Product, Engineering, Compliance, and Operations to embed tax logic into core systems
• Act as the primary point of contact for audits, regulators