Questrade Financial Group (QFG), through its companies - Questrade, Inc., Questrade Wealth Management Inc., Community Trust Company, Zolo, and Flexiti Financial Inc., provides securities and foreign currency investment, professionally managed investment portfolios, mortgages, real estate services, financial services and more. Questrade uses cutting-edge technologies to develop innovative products that give customers better, more affordable ways to take control of their money.

We are everything a traditional financial institution is not. At QFG, you will be constantly moving forward, bringing the future of fintech into existence. You will be a part of a collaborative team that cares deeply about our mission and each other. Your team members will help you conquer challenges, push boundaries and discover what you are truly capable of.

At QFG, we have a culture of innovation where technology serves people—both our team and our customers. We see AI as a collaborative and transformative enabler, and we are seeking forward-thinking individuals who can effectively integrate it into their daily work. The ideal candidate will be a catalyst for change, helping us use AI to create a more efficient and rewarding employee experience while also developing cutting-edge solutions that delight and serve our customers. Join us in shaping a future where AI empowers our team to do their best work and helps us deliver unparalleled customer experiences.

This is a place where you can explore, discover and learn with continuous growth. As a diverse and inclusive place to work, with a hybrid working environment you can unleash your creativity and curiosity with no limits. If you share the same 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 Senior Manager, Tax Reporting & Cost Basis. 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 also obligated to obtain appropriately sufficient documentation from clients to identify their tax residency.

The Senior Manager, Tax Reporting & Cost Basis is a strategic leadership role responsible for the end-to-end execution, integrity, and regulatory compliance of tax reporting and cost basis administration at Questrade. This individual oversees a comprehensive portfolio that includes Canadian Tax Reporting (across Registered Plans and Non-registered accounts), US Tax Reporting, and the critical Cost Basis administration function for all clients.

Leading a team of three specialized Supervisors, the Senior Manager ensures that all annual filing submissions to the CRA, MRQ, and IRS are executed with surgical precision and absolute accuracy within established deadlines. As a seasoned expert, this role is accountable for establishing robust controls, driving large-scale process improvements, and managing high-level escalations. The Senior Manager acts as a key liaison with regulatory bodies and internal stakeholders, ensuring Questrade maintains its position as a leader in tax reporting excellence.

Need more details? Keep reading…

In this role, responsibilities include but are not limited to:

Strategic Leadership & Team Management

• Directly lead and mentor three teams (Tax Reporting for Registered Plans, Canadian Tax Reporting for Non-Registered Accounts; and US Tax Reporting for Non-Registered Accounts), providing high-level guidance and fostering a culture of professional growth and accountability.
• Oversee resource planning, staff scheduling, and performance management for the broader Tax Reporting department.
• Define and monitor departmental KPIs, SLAs, and internal controls to ensure operational excellence and risk mitigation.
• Collaborate with the Operational Excellence team to create and implement a robust learning and development framework that enables swift onboarding of employees and ensures continuous up/cross skilling of staff.
• Oversee daily BPO performance against key metrics for outsourced functions and strictly enforce Service Level Agreements (SLAs).
• Identify performance gaps and conduct root-cause analysis to implement corrective action for any missed targets.

Financial & Audit Responsibilities

• Direct oversight of the reconciliations and tax payments to government revenue agencies (CRA, MRQ, IRS).
• Hold Post-Season Reviews for the most recent fiscal year to identify and build-in required improvements.
• Conduct internal policy and procedure reviews and updates annually.
• Maintain satisfactory internal and external Audit/Regulatory Reviews.

Canadian & US Tax Reporting Oversight

• Own the lifecycle of Canadian tax reporting for both Registered Plans (TFSA, RRSP, FHSA, etc.) and Non-registered accounts (Cash and Margin), ensuring accurate production of all tax slips (T4s, T5s, T3s, NR4s, 1042, and K-1 ).
• Oversee the execution of US Tax Reporting requirements, ensuring compliance with IRS regulations and withholding tax obligations.
• Full accountability over CRS and FATCA reporting.
• Accountable for the successful and timely delivery of annual filing submissions to CRA, MRQ, and the IRS with absolute accuracy.
• Oversee complex amendment and remediation processes across all jurisdictions, ensuring corrections are filed promptly to minimize penalty risks.
• Act as a subject matter expert for high-level decision-making regarding Non-Qualified Investments (NQI) and complex estate settlements.
• Ensure regulatory obligations are met regarding obtaining documentation to identify client tax residency and determining subsequent withholding obligations.

Cost Basis Administration

• Lead the Cost Basis administration function, ensuring the integrity of cost basis data across all client accounts.
• Oversee the resolution of complex cost basis adjustments and ensure systems are aligned with industry standards and CIRO requirements.
• Identify and drive initiatives to enhance cost basis tracking and reporting capabilities.
• Lead cross-functional collaboration with internal and external product and technology partners to improve the firm’s infrastructure for capturing cost basis accurately across multiple systems and platforms.

Compliance, Risk & Process Improvement

• Perform ongoing gap analysis of Questrade’s compliance with evolving tax rules and research implications of new regulations.
• Drive continuous process improvement to enhance the quality, efficiency, and scalability of tax operations.
• Lead the relationship with internal/external auditors and regulatory bodies regarding tax and cost basis matters.
• Act as the final escalation point for complex or high-net-worth (HNW) client queries, maintaining exceptional levels of service.
• Coordinate the QI periodic review and certification of compliance every three years on behalf of the QI Responsible Officer.
• Be the subject-matter expert in all aspects of tax compliance, including Canadian tax, Qualified Intermediaries (QI), Foreign Account Tax Compliance Act (FATCA) and Common Reporting Standard (CRS) requirements, 871(m), 1446, or other withholding and reporting regimes.
• Work with tax authorities on all tax matters, and play a crucial role in ensuring that Questrade’s brand and reputation is protected by adhering to our compliance and risk framework.
• Champion automation & technology integration to streamline operations, reduce manual tasks, and increase scalability.
• Collaborate with Front-office, Product,and CX teams to streamline cross-departmental processes and implement redesigned workflows that focus on customer service and experience.
• Contribute to Business Testing and Release Readiness, for seamless and effective integration, release, and operation of new or enhanced processes, products and technologies.
• Champion a long-term vision for deep AI integration and adoption.

So are YOU our next Senior Manager, Tax Reporting & Cost Basis? You are if you…

• Have a University degree in Finance, Accounting, Economics, or a related field; a professional designation (CPA, CFP) is highly preferred.
• Have 8+ years of relevant experience in tax reporting or related roles, with a minimum of years in a leadership role managing other people leaders.
• Have expert knowledge of Canadian Registered Plan rules (TFSA, RRSP, FHSA, etc.) and deep familiarity with CRA/MRQ year-end reporting forms.
• Have strong expertise in US Tax Reporting (QI/FATCA) and Cost Basis administration principles.
• Have advanced analytical skills and a "detective" mindset for identifying root causes in large datasets.
• Have exceptional leadership skills with a proven ability to coach and develop high-performing teams.
• Have strong proficiency in Excel/Google Sheets (VLOOKUPs, Pivot Tables) and experience with complex financial software.
• Have excellent communication skills, with the ability to simplify complex tax concepts for diverse audiences.
• Have experience using Broadridge’s BPS and TFP systems.
• Have a firm grasp of CIRO investment dealer requirements and a commitment to maintaining the highest standards of data privacy and accuracy.
• Are an enthusiastic team player who demonstrates an infectious positive attitude and leads by example.
• Have clear written and verbal communication skills to explain complex tax implications to internal stakeholders and your team, with an ability to quickly train and onboard junior employees.
• Have excellent analytical and problem-solving skills, with an extraordinary attention to detail.
• Have strong critical thinking and ability to decompose complex concepts into simple and compelling messages.

Compensation Information:

• Base salary range: $140,000 - $155,000
• 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!

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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.