Senior Advisor, Tax Planning

Build something people love

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.

The Role

As a Senior Tax Planner on our Wealth Management team, you'll ensure that financial plans built for our high-net-worth clients are optimized for tax efficiency. Your job isn't to build a financial plan from scratch — it's to take an already sound plan and push it further: identifying every applicable strategy and maximizing tax alpha for each and every wealth management client we serve.

This is a role for someone who thinks like both a tax expert and a financial planner. You'll need the technical depth to spot the strategy, and the CFP-level fluency in financial planning to know how it fits into the bigger picture of a client's plan.

We move fast here, and we expect this role to move with us. Naive ambition is one of our core values — and this team pushes hard to find better, faster ways to do the work, including using AI as a genuine extension of how we operate.

Unlike traditional roles in this space, this position is fully salaried with no commission structure or sales targets.

What You'll Do

• Review and optimize financial plans across our $1MM–$3MM client segment (with some exposure up to $5MM), ensuring every applicable tax strategy has been identified and applied

• Maximize tax alpha for every wealth management client — finding the incremental value that even a good plan misses

• Act as the internal liaison to our Advisor team on complex tax strategies, including building and modeling those strategies as needed

• Apply your expertise to complex situations involving corporations, trusts, and estates

• Support occasional client-facing conversations on sophisticated tax planning questions — note that you will not be providing specific tax advice directly to clients or acting in the capacity of their accountant

• Contribute to the ongoing evolution of our "CPA Designed" financial planning offering

• Bring an AI-native mindset to the role — using AI tools to work faster, model strategies more efficiently, and raise the bar on what the team can deliver

What You Bring

• CPA designation required

• CFP designation required, with genuine comfort and fluency in financial planning — this isn't a tax-only role

• 5+ years of experience in tax planning, wealth management, or financial advisory roles

• Strong knowledge of Canadian tax law and financial planning strategies

• Proven track record of implementing effective tax optimization strategies for HNW clients

• Experience with Conquest strongly preferred

• Excellent communication skills, with the ability to explain complex tax concepts clearly to advisors and clients alike

• A client-first mentality in everything you do

• An AI-native mindset and enthusiasm for using AI tools to move faster and work smarter

• Bilingual (English/French) capability is a significant asset

Why You'll Love Working Here

• A purpose-driven role focused on client outcomes, not sales targets

• The chance to challenge industry norms and put clients first, for real

• A fast-moving, ambitious team that isn't satisfied with the status quo

• Access to cutting-edge fintech tools and an AI-forward way of working

• Career growth in a rapidly expanding company

• Competitive salary and benefits package

• Be part of revolutionizing how wealth management is delivered in Canada

Why Wealthsimple?

🌸 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.

ICYMI

Technology & 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.