Senior Manager, Tax Reporting & Cost Basis5700 Yonge St, North York, ON M2N 5M9, CanadaOverviewQuestrade Financial Group (QFG) provides securities and foreign currency investment, professionally managed investment portfolios, mortgages, real estate services, financial services and more. Questrade uses cutting-edge technologies to develop innovative products. This role focuses on end-to-end execution, integrity, and regulatory compliance of tax reporting and cost basis administration across Canadian and US tax reporting for all clients.ResponsibilitiesStrategic Leadership & Team Management – Directly lead and mentor three teams (Tax Reporting for Registered Plans, Canadian Tax Reporting for Non-Registered Accounts, and US Tax Reporting for Non-Registered Accounts); oversee resource planning, staff scheduling, performance management, and development of a learning framework with the Operational Excellence team.Compliance & Operational Excellence – Oversee daily BPO performance against key metrics, enforce SLAs, monitor KPIs, and drive risk mitigation through root-cause analysis and corrective action for missed targets.Financial & Audit Oversight – Direct reconciliations and tax payments to CRA, MRQ, and IRS; conduct Post-Season Reviews and annual policy/procedure reviews; maintain satisfactory Audit/Regulatory Reviews.Tax Reporting Oversight – Own Canadian tax reporting lifecycle for Registered Plans and Non-registered accounts; ensure accurate production of tax slips; oversee US tax reporting,



CRS and FATCA; manage amendmentsand remediation across jurisdictions; advise on Non-QualifiedInvestments and estate settlements; ensure documentation toidentify client tax residency and withholding obligations.Cost Basis Administration – Lead the cost basis function, ensure data integrity across all client accounts, resolve complex adjustments, and align systems with industry standards and CIRO requirements; drive improvements to tracking and reporting capabilities.Compliance, Risk & Process Improvement – Perform gap analyses on tax rule compliance, drive process improvements for quality, efficiency, and scalability; manage relationships with internal/external auditors and regulators; act as escalationpointfor complex or high-net-worth queries; coordinate QI reviews/certification every three years.Automation & Technology – Champion automation and AI integration to streamline operations; collaborate with Front-office, Product, and CX teams to redesign workflows and improve customer service; contribute to business testing and release readiness for new processes and technologies.Stakeholder Collaboration – Work with tax authorities, internal stakeholders, and product/technology partners to protect the firm’s compliance and reputation.QualificationsUniversity degree in Finance, Accounting, Economics,



or related field; CPA/CFP (preferred).8+ years in tax reporting or related roles; proven leadershipexperience with people management.Expert knowledge of Canadian Registered Plan rules and CRA/MRQ year-end reporting forms; strong US Tax Reporting(QI/FATCA) and Cost Basis experience.Advanced analytical skills with a strong attention to detail; ability to identify root causes in large datasets.Exceptional leadership, coaching, and communication skills; ability to explain complex tax concepts to diverse audiences.Proficiency in Excel/Google Sheets (VLOOKUP, Pivot Tables) and experience with complex financial software; experience with Broadridge BPS/TFP is a plus.Understanding of CIRO requirements and data privacy standards.Solid collaboration, training, and onboarding capabilities; ability to decompose complex concepts into explicit messages.Compensation & BenefitsBase salary range: $140,000 - $155,000Comprehensive benefits package; bonus program forFull-Time Permanent rolesHybrid work environment with at least 3 days in-officeHealth & wellbeing resources, paid vacation, personal and sick daysCareer growth and opportunities to contribute to community causesNotesThis job posting is for an existing vacancy.We’re looking for our next Senior Manager, Tax Reporting & Cost Basis. Could It Be You?Questrade Inc. has multiple client tax reporting obligations to CRA, MRQ, and IRS and requires documentation to identify client tax residency.Application– This posting may include AI-assisted screening. Candidates selected for an interview will be contacted directly. If accommodation is required, please let us know.#J-18808-Ljbffr

📌 Senior Manager, Tax Reporting & Cost Basis - C$140,000 - C$155,000 A Year (Winnipeg)
🏢 Questrade Financial Group
📍 Winnipeg