Supervisor, U.S. Tax Reporting & Cost Basis

Flexiti Financial
Flexiti Financial

People & HR, Operations

North York, Toronto, ON, Canada

CAD 100k-140k / year

Posted on Sep 2, 2026
What’s in it for you as an employee of QFG? Health & wellbeing resources and programs Paid vacation, personal, and sick days for work-life balance Competitive compensation and benefits packages Work-life balance in a hybrid environment with at least 3 days in office Career growth and development opportunities Opportunities to contribute to community causes Work with diverse team members in an inclusive and collaborative environment This job posting is for an existing vacancy. We’re looking for our next Manager, U.S. Tax Reporting & Cost Basis. Could It Be You?Questrade Inc. has multiple client tax reporting obligations to various regulators, including the Canada Revenue Agency (CRA), Ministère du Revenu du Québec (MRQ), and the Internal Revenue Service (IRS). We are seeking a Manager, U.S. Tax Reporting and Cost Basis to lead and monitor daily team activities, ensuring that timeliness, accuracy, and a positive customer experience remain front and center. The ideal candidate will be our Subject Matter Expert (SME) on U.S. taxation (specifically IRS 1042 and 1099 reporting for Canadian non-registered accounts) and adjusted cost basis (ACB) for securities. You will review processes affecting client tax reporting, resolve complex client issues, and drive continuous improvement. Additionally, you will assist the Senior Manager in scoping project requirements, managing process documentation, and conducting user acceptance testing for system changes. Need more details? Keep reading…Tax Reporting Act as the firm's SME with expert knowledge in preparing and filing 1099 and 1042 tax slips with the IRS. Lead and monitor periodic and ad-hoc activities to ensure successful Canadian and U.S. client tax reporting. Prepare and monitor XML filings and manage the reconciliation of internal tax remittance accounts with respective regulatory bodies. Lead discussions to guarantee the accurate classification of securities and income for tax reporting. Ensure timely remittance of payments to the IRS, and assist management as a key point of contact with the IRS. Conduct audits of client documentation to strictly meet Qualified Intermediary (QI), FATCA, and CRS 2.0 requirements. Maintain general knowledge in the preparation of additional slips such as T5, T3, T5013, NR4, T5008, T1135, Realized Gain/Loss reports, and K-1s. Cost Basis Ensure accurate cost basis information is consistently reflected in all client accounts. Review complex reorganization and entitlement events to accurately determine taxable/non-taxable treatment and resulting cost basis. Demonstrate a comprehensive understanding of client-level cost basis calculations across all transaction types (buys, sells, corporate actions). Manage and track ACB vs. ACB per share, including the effects of transfers-in, adjustments, and corporate actions (e.g., dividends, splits) on transaction-level cost basis. General Manage the distribution of client tax reporting cases, ensuring timely resolution and providing recommendations for complex issues. Maintain the team by recruiting, training, and coaching employees, while creating personal growth opportunities in a collaborative work environment. Schedule weekly team meetings, conduct performance appraisals, and communicate clear job expectations. Lead process improvement initiatives, collaborating with peers and department heads to implement efficiencies affecting cross-functional teams. Oversee applicable outside service providers to ensure all Service Level Agreements (SLAs) are met. Coordinate internal resources for department-wide projects alongside Tax Managers, Project Managers, and Business Analysts. So are YOU our next Manager, U.S. Tax Reporting & Cost Basis? You are if you…Education University or post-graduate degree Tax related courses, or industry designations such as CSC, CPA would be an asset Work experience 3+ years experience in client tax reporting, ideally within the brokerage industry 1+ years of experience in people leadership role strongly preferred, ideally with client tax reporting Hard skills Recognized SME in U.S. client tax reporting and filing processes (specifically 1042 and 1099). Deep understanding of U.S. withholding certificates (e.g., W-9s, W-8s) and the complex QI end-to-end process. In-depth knowledge of FATCA and CRS 2.0 requirements. Working knowledge of dividends, income processing, registered plans, and complex reorganizations. Proficiency with book of records, back-office operational systems, and database queries (e.g., SQL, Microsoft Access). Advanced Excel skills required for managing large datasets. Knowledge of Broadridge BPS and Tax Form Plus systems, as well as Google Suite, is an asset. Additional kudos if you… Excellent written and verbal communication skills. Detail-oriented and capable of working collaboratively in a fast-paced, deadline-driven environment. Strong analytical, research, and problem-solving skills tailored for managing complex financial data. Self-motivated with a continuous improvement mindset and the ability to inspire others. Passionate about delivering an exceptional and positive client experience. Professional Development Recommendations: Supervisory Skills courses Industry conferences CPA tax courses Compensation Information: Base salary range: $100,000 -$140,000 The final compensation package will be commensurate with the successful candidate's experience, skills, and geographic location (Canada). It includes a comprehensive benefits plan and a competitive incentive (bonus) program for Full-Time Permanent roles. Sounds like you? Click below to apply!#LI-Hybrid, #LI-Onsite