Manager, Tax Reporting and Cost Basis

Who We Are: Alpaca is a US-headquartered self-clearing broker-dealer and brokerage infrastructure for stocks, ETFs, options, crypto, fixed income, 24/5 trading, and more. Our recent Series D funding round brought our total investment to over $320 million, fueling our ambitious vision. Amongst our subsidiaries, Alpaca is a licensed financial services company, serving hundreds of financial institutions across 40 countries with our institutional-grade APIs. This includes broker-dealers, investment advisors, wealth managers, hedge funds, and crypto exchanges, totalling over 9 million brokerage accounts. Our global team is a diverse group of experienced engineers, traders, and brokerage professionals who are working to achieve our mission of opening financial services to everyone on the planet. We're deeply committed to open-source contributions and fostering a vibrant community, continuously enhancing our award-winning, developer-friendly API and the robust infrastructure behind it. Alpaca is proudly backed by top-tier global investors, including Portage Ventures, Spark Capital, Tribe Capital, Social Leverage, Horizons Ventures, Unbound, SBI Group, Derayah Financial, Elefund, and Y Combinator. Our Team Members: We're a dynamic team of 230+ globally distributed members who thrive working from our favorite places around the world, with teammates spanning the USA, Canada, Japan, Hungary, Nigeria, Brazil, the UK, and beyond! We're searching for passionate individuals eager to contribute to Alpaca's rapid growth. If you align with our core values—Stay Curious, Have Empathy, and Be Accountable—and are ready to make a significant impact, we encourage you to apply. 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 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. 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