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

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

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

Remote (Worldwide)

Team size: 230. Structure: globally distributed

Alpaca is hiring a Director, Tax Reporting and Cost Basis