Manager, Tax Reporting and Cost

Role Summary

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.

• 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‑8
  
  BEN, W‑8
  
  BEN‑E, and W‑8
  
  IMY 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.

• 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‑8
  
  IMY 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.

• 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.

• 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.