Director, Tax Reporting and Cost Basis

Your Role:

As the Manager, Tax Reporting and Cost Basis, you will serve as the right-hand and operational backup to the Senior Manager of Tax Reporting and Cost Basis Operations. This role combines hands-on execution with strategic oversight, ensuring tax reporting, cost basis, and withholding operations run smoothly, accurately, and on time.

You will play a critical role in ensuring accurate U.S. tax reporting, withholding, and regulatory compliance across domestic and cross-border accounts, including fully disclosed and omnibus-style arrangements, while partnering closely with Product, Engineering, and Operations to scale and mature Alpaca’s tax program.

Things you get to do:

• Lead annual tax reporting cycles, including timely and accurate production of Composite 1099 statements and Forms 1042-S
• Execute and oversee withholding agent responsibilities under Chapter 3, Chapter 4 (FATCA), and backup withholding
• Prepare, file, and reconcile Forms 1042 and 945, including timely tax deposits and reconciliation of reported amounts
• Ensure compliant setup and execution of tax reporting and withholding for complex ownership structures, including: Qualified Intermediaries, Non-Qualified intermediaries, fully disclosed and omnibus arrangements
• Serve as an internal SME on beneficial owner determination, withholding rates, and reporting responsibility
• Review and operationalize W-8BEN, W-8BEN-E, and W-8IMY documentation, including withholding statements and income allocation
• Manage Alpaca’s tax reporting vendor, FIS, relationship, including data quality, error and warning remediation, delivery timelines, and process improvements
• Coordinate and respond to tax-related audits, examinations, and IRS notices (e.g., CP2100)
• Act as a backup to the Senior Manager, ensuring continuity of tax reporting and cost basis operations
• Partner with Product, Engineering, Legal, and Compliance on tax reporting requirements, system enhancements, and program scalability

Who you are (Must Haves):

• 3+ years of hands-on tax reporting and/or cost basis experience at a securities broker-dealer
• Direct experience with Composite 1099 statements and Forms 1042-S production
• Working knowledge of Chapter 3 and Chapter 4 withholding and reporting requirements
• Working knowledge of Form W-8IMY analysis and application, such as Qualified Intermediaries, Non-Qualified intermediaries and both fully disclosed and omnibus arrangements
• Experience acting as or supporting a withholding agent
• Series 7 registration (or ability to obtain)
• Strong understanding of IRS regulations covering securities products (equities, options, fixed income)
• Exceptional attention to detail with strong documentation and reconciliation skills
• Comfortable operating in evolving environments where processes are still being built
• Proven ability to manage multiple priorities while maintaining accuracy and deadlines
• Clear communicator across Slack, email, and ticketing systems with a strong sense of ownership

Who You Might Be (Nice-to-Haves):

• Bachelor’s degree or equivalent practical experience
• Experience supporting a global or cross-border customer base
• Familiarity with Chapter 3, Chapter 4, and FATCA classifications, withholding statements, and complex ownership structures
• Exposure to digital asset tax reporting and emerging regulatory requirements
• Process and automation-oriented mindset
• Ability to retain, structure, and document institutional knowledge
• Foundational technical fluency (APIs, data models, system integrations) to partner effectively with Engineering and Product
• Previous experience working with FIS (formerly Wall Street Concepts) Tax Reporting Manager