Senior Associate, U.S Tax Operations , NY

Overview

Clear Street is building new infrastructure for today’s financial institutions. Founded in 2018, Clear Street is an independent, non-bank prime broker replacing the legacy infrastructure used across the capital markets today. We started from scratch by building a completely cloud-native clearing and custody system designed for today’s complex global markets. Clear Street’s proprietary prime brokerage platform adds significant efficiency to the market, while focusing on minimizing risk and cost for clients regardless of size or revenue opportunity.

Our goal is to create a single source-of-truth platform for every asset class, in every country, and in any currency.

The Tax Operations team is globally responsible for ensuring compliance with Clear Street Group; U.S. information reporting and withholding, FATCA, CRS, QI/QDD and securities taxation and filing obligations. The team works closely with all business lines including institutional brokerage, custody and retail businesses. This is an integrated team providing guidance on securities taxation obligations, managing tax risk and running tax processes globally.

• U.S.
  • U.S. Withholding Tax Compliance (Chapters 3, 4, 61, 871(m), 1446(f), 305(c))
  • Cost Basis and Wash Sale Reporting
  • U.S. Tax Information Reporting (Forms 1099, 1042-S, 1042)
  • Nonresident Alien (NRA) withholding and treaty eligibility validation
  • Tax documentation and W-8/W-9 validation
• Europe, North America, APAC
  • European, Asian, Canadian, LATAM securities taxation including Stamp, FTT, Securities Transaction Taxes
  • Dividend withholding and treaty relief across relevant jurisdictions
• Continuous Change
  • Partnering with Legal, Compliance, Operations, and Technology on cross-functional initiatives
  • Driving improvements through automation and process enhancements

The role is an Associate Director of U.S. Tax Operations specializing in Cost Basis. It will be responsible for all aspects of Cost Basis, working closely with third‑party providers, maintaining day‑to‑day records, and ensuring accurate and timely preparation of client reporting and annual 1099 filing. The responsibility also extends to supporting Canadian Cost Basis. In this capacity the role acts as SME for continuous development of the Cost Basis platform and reporting, addressing ongoing regulatory developments and seeking continuous improvements to external platforms and related internal systems.

This hands‑on role requires technical knowledge of U.S. information reporting and withholding obligations and practical experience applying them in a fast‑paced broker‑dealer, custody and retail environment. The successful candidate will ensure accuracy in reporting, apply complex rules and guidance, and work directly with data and systems to deliver results.

• Review and cleanse Cost Basis information day‑to‑day.
• Prepare client‑facing open lot & realized reporting.
• Prepare and file U.S. information returns 1099 Series.
• Prepare Canadian Cost Basis Reporting.
• Prepare and file U.S. information returns including 1042‑S, and related IRS filings.
• Calculate, apply, and reconcile U.S. withholding under Chapter 3, Section 871(m), Section 305(c), and 1446(f).
• Review and validate tax documentation (W‑8/W‑9).
• Perform reconciliations of withholding and reporting data to ensure accuracy and completeness.
• Respond to and support IRS, audit, and regulatory inquiries.
• Execute test cases for Cost Basis, tax reporting and withholding system enhancements.
• Partner with Operations & Technology to resolve data issues and improve automation.
• Maintain detailed process documentation and contribute to continuous process improvements.

• 5‑10 years of hands‑on experience in Cost Basis.
• Experience with U.S. information, reporting & withholding obligations.
• Technical knowledge of IRS obligations under Chapter 3, Chapter 4 (FATCA), Chapter 61, §871(m), and s.1446(a) and (f).
• Practical experience with broker‑dealer, prime brokerage and custodial operations.
• Familiarity with IRS systems (FIRE, EFTPS & the forthcoming IRIS system) and tax documentation platforms.
• Proven ability to work with large data sets, reconcile…