Director, 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 https://alpaca.markets/blog/alpaca-raises-150-million-at-a-1-15b-valuation-to-build-the-global-standard-for-brokerage-infrastructure/ 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 380+ 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  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. Your mandate is to deliver a clean, accurate, and on-time tax season every January, supported by rigorous processes, repeatable playbooks, and proactive system validation throughout the year. 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. https://files.alpaca.markets/disclosures/AlpacaRecruitmentPrivacyPolicy.pdf Offices: (Remote - United States);