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

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 perks packages

Work-life balance in a hybrid environment with at least 3 days in office

Growth opportunities 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 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.

In this role, 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 recent 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

📌 Senior Analyst, U.S. Tax Reporting (Canada)
🏢 Community Trust
📍 Canada