Wealthsimple is Canada’s leading financial innovator. The company offers a full suite of simple, sophisticated financial products across managed investing, do-it-yourself trading, cryptocurrency, tax filing, spending and saving. Wealthsimple currently serves more than 4 million Canadians and holds over $155 billion in assets under administration. The company was founded in 2014 by a team of financial experts and technology entrepreneurs, and is headquartered in Toronto, Canada.
We're proud of what we've built — and we're just getting started. Read our Culture Manual and learn more about how we work.
Job Description: Senior Manager, Client TaxBuild something people loveWealthsimple is Canada’s leading financial innovator. The company offers a full suite of simple, sophisticated financial products across managed investing, do-it-yourself trading, cryptocurrency, tax filing, spending and saving. Wealthsimple currently serves more than 4 million Canadians and holds over $155 billion in assets under administration. The company was founded in 2014 by a team of financial experts and technology entrepreneurs, and is headquartered in Toronto, Canada.
We're proud of what we've built — and we're just getting started. Read our Culture Manual and learn more about how we work.
About the teamThe Client Tax team helps make investing simple, reliable, and compliant for Wealthsimple clients. We lead the systems, processes, controls, and reporting that support tax slips, registered accounts, client statements, withholding, and related regulatory obligations across our growing brokerage business.
About the roleYou’ll lead Wealthsimple’s client tax function across brokerage products and regulated entities, including the people and team capabilities required to deliver the mandate. You’ll be accountable for accurate, timely, and scalable client tax reporting, while building the controls, systems, and operating practices needed to support continued product and client growth. You’ll act as a senior partner to CXO, Product, Engineering, Operations, Compliance, Legal, and Finance, translating complex client tax and regulatory requirements into product design advice with clear decisions and reliable execution. A key part of the role is working closely with CXO to ensure reporting processes, internal & external communications, and issue resolution deliver a clear and reliable client experience.
In this role you'll have the opportunity to:Lead the strategy, operating model, and execution of Wealthsimple’s client tax operating function across Canadian and applicable U.S. requirements.
Own the end-to-end delivery of client tax slips, registered-account reporting, client statements, and related regulatory filings, including readiness, controls, quality assurance, amendments, and regulator communications.
Establish and maintain robust governance for QI, FATCA, CRS, non-resident withholding, and client reporting obligations, ensuring risks and regulatory gaps are identified and addressed.
Trusted advisor and partner to CXO, Product, Engineering, and Operations leaders on new-product client tax treatment and reporting implications, reporting logic, data quality, system requirements, testing, automation, scalable process design, and client-impacting issue resolution, excluding any corporate and sales tax implications.
Lead, coach, and develop the Client Tax team, including setting team priorities, hiring and onboarding, performance management, career development, and standards for accuracy, timeliness, escalation management, client outcomes, and audit readiness.
Implement AI and automation strategies to create significant operational efficiencies and leverage to support our ambition growth and scaling.
Provide clear technical research, recommendations, and executive-level communication on tax reporting issues, regulatory change, control environments, and investment priorities.
8+ years of progressive experience in client tax reporting, financial services tax, brokerage operations, regulatory reporting, or a related function, including significant experience directly leading and developing people.
Deep knowledge of Canadian brokerage tax reporting and registered-account requirements, including relevant CRA, Revenu Québec, and applicable U.S. reporting obligations.
Experience with QI, FATCA, CRS, withholding tax, client statements, book-of-record data, and the control requirements associated with high-volume regulated reporting.
A track record of leading cross-functional programs involving Product, CXO, Engineering, Operations, Compliance, Legal, and external stakeholders.
Strong analytical, communication, and judgment skills, with the ability to turn complex regulatory requirements into strategic product design and practical operating decisions.
CPA designation or equivalent professional qualification.
In-Depth Tax Program or an equivalent Canadian tax specialisation
Experience with CIRO/CRM2/CRM3 reporting, fintech, digital brokerage, or high-growth financial-services environments.
Experience scaling reporting through automation, modern data tooling, and operational-control frameworks.
Experience in a Big Four or national accounting firm, or a comparable advisory environment.
You are a strategic, hands-on leader who can move between technical detail and enterprise-level priorities.
You bring sound judgment in ambiguous or evolving regulatory environments.
You are an experienced people leader who builds high-trust teams with clear expectations, direct feedback, strong development practices, and a healthy performance culture.
You care deeply about accuracy, client outcomes, resilience, and doing the right thing.
You simplify complex topics and create alignment across functions.
🌸 Top-tier health benefits and life insurance
📈 Long-term group savings with employer match, through Wealthsimple for Business
🌴 20 vacation days, 4 wellness days, and unlimited sick and mental health days per year
✈️ 90 days away: work outside Canada for up to 90 days per year
👥 Employee resource groups, including Rainbow (2SLGBTQ), Women of WS, and Black at WS
🌎 We are a hybrid team with over 1,500 employees across North America. The people are one of the best parts of working here: you'll collaborate with incredibly talented, curious, and driven teammates who are deeply committed to doing great work.
ICYMITechnology & Innovation at Wealthsimple: We move quickly and build thoughtfully. That means we're always looking for better ways to work — whether that's new tools, AI, or rethinking how we approach a problem. We don't expect you to have all the answers, but we do expect curiosity and a willingness to evolve alongside the products we're building.
Inclusion Statement: We're building products for a diverse world, and we need a diverse team to do it well. We strongly encourage applications from everyone, regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.
Accessibility Statement: We're committed to an accessible hiring experience. If you need any accommodations throughout the interview process, please let us know — we'll work with you to make sure you have what you need. We also welcome any feedback on how we can better accommodate candidates with accessibility needs.
AI in Hiring: We may use artificial intelligence (AI) tools to support parts of our hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our team but don't replace human judgment – all final hiring decisions are made by people. If you have questions about how your data is used, reach out to us.
