5700 Yonge St, North York, ON M2N 5M9, CanadaJob DescriptionPosted Monday, April 13, 2026 at 4:00 AMQuestrade Financial Group (QFG) is looking for a Supervisor, U.S. Tax Reporting. The role is responsible for planning and monitoring daily activities within the Tax Reporting team, ensuring timeliness and accuracy, providing a positive customer experience, and supporting the Senior Manager with project scope, documentation, change, and testing.What’s in it for you?Health & wellbeing resources and programsPaid vacation, personal, and sick days for work‑life balanceCompetitive compensation and benefits packagesWork‑life balance in a hybrid environment with at least 3 days in officeCareer growth and development opportunitiesOpportunities to contribute to community causesWork with diverse team members in an inclusive and collaborative environmentResponsibilitiesLead and monitor periodic and ad‑hoc Canadian & US client tax reporting activities.Prepare and monitor general tax slips (T5, T3, T5013, NR4, T5008, T1135, 1099, 1042‑S, Realized Gain/Loss report, K‑1).Prepare and monitor XML filings.Lead the tax season project plan to meet or exceed regulatory deadlines.Ensure accurate classification of securities and income for tax reporting.Timely remittance of payments to the CRA, MRQ and/or IRS.Act as point of contact with the IRS.Oversee daily tasks: security and corporate action research, FX conversions, mail and email monitoring and distribution.Supervise the reconciliation of internal tax remittance accounts with regulator accounts.Conduct audits of client documentation to meet QI/FATCA/CRS requirements.Assist with audit activities.Manage distribution of client tax‑reporting cases and recommend solutions for complex issues.Attend industry calls or conferences,



draft call memos and distribute them internally.Review and coach team members on complex re‑organization and entitlement events for tax treatment.Possess deep knowledge of the Complex QI end‑to‑end process.Assist with KPI reports and project status reporting.Ensure accurate cost basis information is reflected in client accounts and review re‑organization events for cost.Conduct interviews and make hiring recommendations.Schedule weekly team meetings and ensure active participation.Recruit, select, orient, and train employees and maintain a collaborative, safe, and legal work environment.Communicate job expectations, plan, monitor and appraise results; coach and discipline employees; enforce policies and productivity standards.Lead team process‑improvement initiatives and inspire others to improve operational processes.Collaborate with peers and department heads to identify and implement process efficiencies affecting tax reporting.Supervise policy and procedure creation and updates.Coordinate internal resources for team, departmental, and organization‑wide projects and support the Tax Manager, Project Managers, and Business Analysts.Oversee external service providers to ensure SLA compliance.Build positive and productive relationships with internal teams and external third‑party providers.Assist in establishing short‑ and long‑term goals by gathering business information and metrics, evaluating options, and defining outcomes.Perform other duties as assigned.Qualifications3+ years of client tax reporting experience,



ideally within the brokerage industry.1+ year of people‑leadership experience, ideally for client tax reporting.University or post‑graduate degree.Subject‑matter expert in Canadian and/or US client tax reporting and filing processes.Deep understanding of U.S. withholding certificates (W‑9, W‑8), Qualified Intermediary requirements, FATCA, and CRS 2.0.Knowledge of dividends, income processing, re‑organization, and registered plans.Experience with book‑of‑records and back‑office operational systems.Knowledge of database queries (SQL), Microsoft Access, and advanced Excel.Excellent written and verbal communication skills.Detail‑oriented, collaborative, and able to work in a fast‑paced, deadline‑driven workplace.Strong work ethic and focus on quality results.Organizational and time‑management skills.Independent, self‑motivated, and able to motivate others to exceed expectations.Ability to manage competing priorities effectively on personal and team levels.Strong research and problem‑solving skills with analytical ability for large datasets.Continuous improvement mindset and desire to implement improvements to completion.Team‑player who is collaborative and flexible.Completed tax‑related courses or industry designations such as CSC or CPA.Knowledge of Broadridge BPS and Tax Form Plus systems.Google Suite experience.CompensationBase salary range: $85,000 - $100,000. The final compensation package will be commensurate with the successful candidate’s experience, skills, and geographic location (Canada) and includes a comprehensive benefits plan and a competitive incentive (bonus) program for full‑time permanent roles.Equal Opportunity Employer. We welcome applicants from all backgrounds.#J-18808-Ljbffr

📌 Supervisor, U.S. Tax Reporting - C$85,000 - C$100,000 A Year (Winnipeg)
🏢 Questrade Financial Group
📍 Winnipeg