Associate Director, Global Tax Operations

About Clear Street:

Clear Street is modernizing the brokerage ecosystem. Founded in 2018, Clear Street is a diversified financial services firm replacing the legacy infrastructure used across capital markets.

We started from scratch by building a completely cloud-native clearing and custody system designed for today’s complex, global market. Clear Street’s proprietary prime brokerage platform adds significant efficiency to the market, while focusing on minimizing risk, redundancy, and cost for clients. Our goal is to create a single source-of-truth platform for every asset class, in every country, and in any currency.

By combining highly-skilled product and engineering talent with seasoned finance professionals, we’re building the essentials to compete in today’s fast-paced markets.

The Role:

The role is Associate Director, leading Canadian Tax Operations reporting to the Global Head of Tax Operations. The role will be responsible for Canadian securities tax obligations for retail, tax-advantaged and institutional client reporting, including CRS/ FATCA account documentation, Canadian cost basis, withholding on non-resident account holders and annual information reporting to CRA and clients.

In this capacity the role will act as SME for continuous development of Clear Street platforms in support of Canadian tax obligations, addressing ongoing CRA regulatory developments and seeking continuous improvements to internal systems and the related external platform.

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

Key Responsibilities:

• Review and approval of CRS RC520/ 521, NR301, NR302, NR303

• Review and cleanse of Canadian Cost Basis information day-to-day

• Regulatory filings NR4, T5, T5008, T3, T5013 TFSA / RRSP / RRIF Slips and Summary

• Reconcile withholding and reporting ensuring accuracy and completeness

• Respond to and support CRA NR76 inquiries, and tax audit

• Partner with Dev Ops & Technology teams to resolve data issues and improve automation

• Maintain detailed process documentation and contribute to continuous process improvements

• Investigation and resolution of tax operations breaks across internal books and records

• Ownership and execution of daily, monthly, and quarterly operational controls, including documentation and evidence retention

• Hiring, managing, and developing tax operations staff

• Driving continuous improvement in controls, processes, and transparency as the platform scales

Requirements:

• 5-10 years of hands-on experience of meeting CRA obligations

• Prior experience at a Canadian broker-dealer or major Canadian financial institution

• Familiarity with CRA reporting and payment systems

• Detailed understanding of regulatory obligations and experience in dealing with the CRA

• Detail-oriented, with a control and risk-focused mindset.

• Practical experience with retail, broker-dealer and custodial operations

• Proven people management experience, including hiring, coaching, and performance management

• Ability to work with large data sets, reconcile reporting / withholding amounts, and identify discrepancies.

• Ability to operate with a high degree of autonomy in a fast-moving environment

• Clear, direct communicator with strong judgment under pressure

We Offer:

At Clear Street, we offer competitive compensation packages, company equity, 401k matching, gender neutral parental leave, and full medical, dental and vision insurance. Our belief has always been that we are better as a business when we are all together in person. As such, we are requiring employees to be in the office 4 days per week. In-office benefits include lunch stipends, fully stocked kitchens, happy hours, a great location, and amazing views.

Our top priority is our people. We’re continuously investing in a culture that promotes collaboration. We help each other through challenges and celebrate each other's successes. We believe that modern workplaces succeed by virtue of having high-performance workforces that are diverse — in ideas, in cultures, and in experiences. We put in the effort to make such a workplace a daily reality and are proud to be an equal opportunity employer. #LIHYBRID