Senior Analyst, U.S. Tax Reporting & Cost Basis

Questrade Financial Group; Toronto; Hybrid; CAD 70,000 - 80,000; Full time

Benefits offered by this job

Health & wellbeing resources

Paid vacation and personal days

Hybrid work environment with 3+ days/週

Career growth and development

Community involvement

Job summary

Questrade Financial Group is seeking a Senior Analyst, U.S. Tax Reporting to manage client tax residency, with emphasis on U.S. and Canadian reporting.

The role involves regulatory compliance across CRA, MRQ, and IRS, and hands-on reporting for 1099/1042 series and related slips. Applicants will analyze tax residency, classify securities, and coordinate remittances and reporting while staying current with QI regulations and IRS guidance.

Qualifications

• Post-secondary education in Finance, Economics, or related field.
• 2+ years in a Tax Reporting role with focus on U.S. and Canadian tax reporting rules.
• 2+ years in an operational/continuous improvement or client service role in financial services.

Responsibilities

• Analyze client account documentation to determine tax residency.
• Prepare and coordinate payment requests for withholding tax remittances.
• Reconcile income and withholding tax accounts and respond to queries.
• Calculate withholdings for manual transactions and various securities actions.
• Process stock dividends, spin-offs, and mergers.
• Enter tax factors and client transactions into tax systems.
• Verify information on U.S. and Canadian investment slips.
• Monitor changes to QI regulations and IRS guidance.

Skills

Analytical skills

U.S. tax reporting

Regulatory knowledge

Excel macros

Coding languages

Research and analysis

Education

Finance/Economics related field

Tools

Excel/Google Sheets

Broadridge systems

Job description

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

We’re looking for our next Senior Analyst, U.S. Tax Reporting. Could It Be You?

Questrade Inc. has multiple client tax reporting obligations to various tax regulators, including the Canada Revenue Agency (CRA), Ministère du Revenu du Québec (MRQ), and the Internal Revenue Service (IRS). We are looking for a Senior Analyst, U.S. Tax Reporting to play a critical role in ensuring we meet these regulatory obligations.

The ideal candidate is a highly analytical self-starter with a strong understanding of U.S. tax regulations. You will be responsible for obtaining client tax residency documentation, classifying securities and income, and ensuring accurate reporting and remittance to regulators. This role requires in-depth research into evolving Qualified Intermediary (QI) regulations and hands-on experience both U.S. (1099, 1042-S, 1042) reporting to IRS.

Responsibilities include but are not limited to:

• Perform periodic tasks to ensure compliance with U.S. and Canadian tax reporting regulations.
• Analyze client account documentation to accurately determine tax residency.
• Prepare and coordinate payment requests for withholding tax remittances to regulators.
• Reconcile income and withholding tax accounts, responding to internal and external tax-related queries.
• Calculate withholdings for manual transactions, including Hybrid/Dual Source securities, 871(m), SEC 302/304, SEC 305C, and Dividends with Options.
• Process Stock Dividends, Spin-Offs, and Merger transactions.
• Enter provided tax factors and client/securities transactions into the tax system.
• Verify information on U.S. investment slips (1099-DIV, 1099-INT, 1099-MISC, 1042-S Aggregate, 1042-S Individual, and Form 1042).
• Validate information on Canadian investment slips (T5, T3, T5013, CRS, and FATCA).
• Continuously monitor and research changes to QI regulations and IRS guidance, ensuring accurate implementation for year-end reporting.
• Research new tax rules and conduct gap analyses to assess their impact on Questrade's clients, systems, and processes.
• Participate in monthly securities research to classify new securities and income (including deemed income), ensuring correct representation on tax slips and appropriate withholding.
• Classify corporate actions to ensure accurate U.S. and Canadian tax withholding and reporting.

So are YOU our next Senior Analyst, U.S. Tax Reporting? You are if you…

Education

• Post-secondary education, preferably in Finance, Economics, or related field

Work Experience

• 2+ years of prior work experience in a Tax Reporting role, focusing on research and analysis of U.S. and Canadian tax reporting rules (strongly preferred).
• 2+ years of experience with U.S. client tax reporting (strongly preferred).
• 2+ years in an operational, continuous improvement, or client service role, ideally within a financial services organization.
• Experience writing operational proposals based on external research or internal gap analysis is an asset.

Hard Skills

• Strong knowledge of client/securities taxation rules, operational impacts, and U.S./Canadian client tax reporting.
• Strongly preferred knowledge of security types, income types, and corporate actions.
• Experience with Qualified Intermediary (QI) obligations.
• High Intermediate to Advanced knowledge of Excel or Google Sheets (strongly preferred).
• Understanding of the securities industry and IIROC-regulated brokerage operations.
• Ability to build macros and knowledge of coding languages (preferred).
• Experience with Broadridge systems is a nice-to-haves.

Additional Kudos If You…

• Expert research, analytical, and problem-solving skills, capable of managing large datasets.
• Excellent written and verbal communication skills.
• Detail-oriented, self-motivated, and capable of working independently with minimal supervision.
• Strong organizational skills and a results-focused, deadline-driven work ethic.
• Collaborative team player with a strong customer service and continuous improvement mindset.

Compensation Information:

• Base salary range: $70,000- $80,000
• 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.

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.