Director, Tax Reporting and Cost Basis

About the role

This role is central to Alpaca's financial operations, requiring the Director to define and execute the company's global tax reporting strategy. A primary responsibility will be to lead the development of a proprietary cost basis engine, working closely with engineering teams. The position involves ensuring accurate and timely reporting across various regulatory frameworks, including 1099, 1042-S, and 5498, with an initial focus on U.S. requirements that will expand to support international clients.

The Director will be responsible for establishing a year-round tax readiness program, which includes multiple testing cycles and reconciliations to validate systems and data. This preparation culminates in owning the successful delivery of the January tax season, adhering to clear guidelines and operational metrics. Success in this role means building and scaling a high-performing team while partnering with Product, Engineering, Compliance, and Operations to integrate tax logic into core systems.

Alpaca is a U.S.-headquartered broker-dealer providing infrastructure for various financial assets, including stocks, ETFs, options, and crypto. The company serves financial institutions across 40 countries, managing over 9 million brokerage accounts. The global team is composed of experienced engineers, traders, and brokerage professionals, with a commitment to open-source contributions and enhancing their developer-friendly API.

The salary for this role ranges from $135,000 to $225,000 USD annually, reflecting a senior-level position with specialized expertise.

Skills that matter here

• brokerage tax reporting: This role requires leading the overall tax reporting strategy for a brokerage firm, ensuring compliance with various regulations.
• cost basis: A key responsibility is to design and build a proprietary engine for calculating cost basis, a fundamental aspect of tax reporting.
• U.S. expertise: The role demands deep knowledge of U.S. tax regulations to establish a foundational reporting strategy before expanding internationally.
• financial calculation system: Experience in developing or leading the creation of systems that perform complex financial calculations, such as a cost basis engine, is essential.
• 1099-COMP: The Director will oversee reporting obligations related to various forms, including 1099-COMP, ensuring accuracy and compliance.
• team leadership: This position involves building, scaling, and managing a high-performing team to deliver accurate and timely tax reporting cycles.

Who this role suits

• A candidate with over a decade of experience specifically in brokerage tax reporting and cost basis.
• Someone who has hands-on experience building or leading the development of financial calculation systems.
• An individual with a strong understanding of U.S. tax forms like 1099-COMP, 1042-S, and 5498, including retirement account considerations.
• A leader capable of operating at both a strategic level to define global tax strategy and a deeply operational level to ensure execution under pressure.

From the employer

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.