Supervisor, U.S. Tax Reporting & Cost Basis

Kinvie; Canada; Hybrid; CAD 100,000 - 140,000; Full time

Benefits offered by this job

Health & wellbeing resources

Paid vacation and personal days

Hybrid work environment (3 in office)

Job summary

Questrade Financial Group is seeking a Manager, U.S. Tax Reporting & Cost Basis to lead and optimize US tax reporting for Canadian accounts, including 1042/1099 filings and cost basis management.

You will guide a cross-functional team to ensure accuracy, timeliness, and regulatory compliance with QI, FATCA, and CRS standards in a hybrid workplace.

The role demands SME-level knowledge, strong Excel/SQL skills, and proven leadership to drive improvements and systemic accuracy.

Qualifications

• University or post-graduate degree required or equivalent
• Tax knowledge and experience with U.S. reporting (1042/1099) highly preferred
• 3+ years in client tax reporting, brokerage experience ideal
• 1+ years in people leadership role preferred
• Ability to use SQL and data tools for large datasets

Responsibilities

• Act as SME for U.S. tax reporting, including 1042/1099 filings with IRS
• Lead and monitor tax reporting activities ensuring timeliness and accuracy
• Manage cost basis calculations and reconciliation across accounts
• Review complex reorganization events affecting cost basis
• Oversee SLAs and coordinate with IT, tax, and operations teams
• Coach and develop team members, drive process improvements

Skills

Advanced Excel

SQL

Data analysis

Leadership

Education

University or post-graduate degree

Tax-related certifications preferred

Tools

Broadridge BPS

Tax Form Plus

Microsoft Access

Google Suite

Job description

5700 Yonge St, North York, ON M2M 4K2, Canada

Job Description

Posted Tuesday, September 1, 2026 at 6:00 AM

Questrade Financial Group (QFG), through its companies - Questrade, Questbank, Questrade Wealth Management, Community Trust Company, Zolo, and Flexiti, provides securities and foreign currency investment, professionally managed investment portfolios, mortgages, real estate services, financial services and more. We use cutting-edge technology to help Canadians become much more financially successful and secure.

At QFG, we combine human-centric collaboration with AI-driven innovation to redefine financial services. The ideal candidate will be a catalyst for change, using AI to transform and deliver unparalleled customer experiences and shaping a future where AI empowers our teams to do their best work.

Join our diverse, inclusive, and hybrid workplace to unleash your creativity and nurture your curiosity without limits. If you share this sense of infinite possibility, come shape your future at QFG.

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.

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

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

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.

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.

#LI-Hybrid, #LI-Onsite

At Questrade Financial Group of Companies, with multiple office locations around the world, we are committed to fostering a diverse, inclusive and accessible work environment. This is an environment where individuals are treated with dignity and respect. Here, the unique skills and experience you bring will be valued. You will be supported and motivated, so that you can harness your unlimited potential. Our team reflects the diversity of the communities we serve and operate in. Having a collaborative and diverse team helps us push boundaries to bring the future of fintech into existence—not only for the benefit of our customers, but for those who build their career with us.

Questrade Financial Group of companies Applicant Tracking System utilizes artificial intelligence (AI) for application screening. The AI system operates on predetermined criteria, with final decisions subject to human review.

Candidates selected for an interview will be contacted directly. If you require accommodation during the recruitment/selection process, please let us know and we will work with you to meet your needs.

5700 Yonge St, North York, ON M2M 4K2, Canada