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Wealthsimple, Canada's leading financial innovator with 4+ million clients and $155B+ in assets under administration, is seeking a Senior Manager of Client Tax to lead its client tax function across brokerage products and regulated entities.
You will own the end-to-end delivery of client tax slips, registered-account reporting, client statements, and regulatory filings across Canadian and applicable U.S. requirements. This includes establishing robust governance for QI, FATCA, CRS, non-resident withholding, and client reporting obligations, ensuring risks and regulatory gaps are identified and addressed.
Key responsibilities include:
- Leading strategy, operating model, and execution of the client tax function across Canadian and U.S. requirements
- Owning readiness, controls, quality assurance, amendments, and regulator communications for tax reporting deliverables
- Serving as trusted advisor to CXO, Product, Engineering, and Operations on new-product tax treatment, reporting logic, data quality, system requirements, and scalable process design
- Leading, coaching, and developing the Client Tax team, including hiring, performance management, and career development
- Implementing AI and automation strategies to drive operational efficiencies and support growth
- Providing technical research, recommendations, and executive-level communication on tax reporting issues and regulatory change
You bring 8+ years of progressive experience in client tax reporting, financial services tax, brokerage operations, or regulatory reporting, with significant people-leadership experience. Deep knowledge of Canadian brokerage tax reporting, registered-account requirements, CRA/Revenu Québec obligations, and U.S. reporting is essential. Experience with QI, FATCA, CRS, withholding tax, and high-volume regulated reporting is required. You have a track record of leading cross-functional programs and translating complex regulatory requirements into strategic product design and practical operating decisions.
Nice-to-have qualifications include CPA designation, In-Depth Tax Program certification, experience with CIRO/CRM2/CRM3 reporting, fintech/digital brokerage background, experience scaling reporting through automation and modern data tooling, or Big Four/national accounting firm experience.
You are a strategic, hands-on leader who moves fluidly between technical detail and enterprise-level priorities. You bring sound judgment in ambiguous or evolving regulatory environments and are an experienced people leader who builds high-trust teams with clear expectations, direct feedback, and strong development practices.
