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.

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, and external stakeholders on tax reporting matters

Who You Are (Must Haves)

• 10+ years of experience in brokerage tax reporting and cost basis, with deep U.S. expertise
• Hands-on experience building or leading the development of a cost basis engine or similar financial calculation system
• Strong knowledge of 1099-COMP, 1042-S, 5498, and contribution reporting, including retirement account considerations
• Experience supporting global clients, including understanding of withholding, treaty rates, and cross-border tax implications
• Proven ability to design scalable systems, controls, and processes from scratch
• Track record of leading teams and delivering accurate, on-time tax reporting cycles
• Ability to operate at both strategic and deeply operational levels, especially under time-sensitive conditions

Who You Might Be (Nice-to-Haves)

• Experience building a residence vs. security domicile matrix for treaty rate application
• Background in API-first brokerages, clearing firms, or multi-asset platforms
• Familiarity with international tax regimes and reporting beyond the U.S.
• Experience running mock tax seasons, parallel runs, or large-scale system validation cycles
• CPA or equivalent certification
• Experience working directly with regulators or leading large-scale audits

How We Take Care of You:

• Competitive Salary & Stock Options
• Health Benefits
• New Hire Home-Office Setup: One-time USD $500
• Monthly Stipend: USD $150 per month via a Brex Card

Alpaca is proud to be an equal opportunity workplace dedicated to pursuing and hiring a diverse workforce.