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

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.

Manager, Tax Reporting, Cost Basis

About this role