Estate Planning Specialist, Wealth Management

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.

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

This is the first role of its kind at Wealthsimple. As our Estate Planning Specialist, you'll build the foundation of how we review and optimize estate plans for our Wealth Management clients — an area that many HNW clients fail to properly address, even when the rest of their financial plan is sound.

You'll join a growing specialist bench that already includes our Tax Planning team and our Family Enterprise Advisor. Like those functions, your job isn't to draft legal documents or sell products — it's to review clients' existing wills, trust documents, and broader estate plans, identify where they no longer align with (or never accounted for) the client's actual goals, and clearly explain in plain language what needs to change and who can help make that happen.

This is not a sales role and will not be selling insurance, or anything else. Your job is to advocate for the client's best interests — identifying gaps and misalignments, and connecting clients to the right resource to solve them, whether that's our estate lawyer referral network, our documentation-drafting partners.

As the newest Specialist to the team, you won't just be executing an established process — you'll be responsible for helping design and build the estate review and planning process itself, in partnership with the Wealth Management leadership team. Naive ambition is one of our core values, and this role is a chance to define, from scratch, what great estate planning support looks like for HNW clients in Canada.

This position is fully salaried, with no commission structure or sales targets.

What You'll Do

• Review clients' existing wills, trust documents, and broader estate plans to assess whether their current form and structure will actually accomplish the client's goals
• Clearly identify and articulate, in plain language, where an estate plan is misaligned with a client's goals — and what specifically needs to change
• Lay out the concrete next steps a client needs to take, and connect them to the right resource to take them — whether that's a referral to our estate lawyer network for will or trust drafting, a partner such as Willful, or another appropriate solution
• Apply a deep understanding of trusts to identify planning opportunities and gaps across complex, multi-entity estates
• Review existing insurance policies as one input into the overall estate plan — assessing how a policy does or doesn't support the client's estate goals
• Act as the internal liaison to our Advisor team, supporting them on complex estate planning cases and client conversations where they need additional expertise
• Support client-facing conversations on sophisticated estate planning questions, in partnership with the client's advisor
• Help design and build Wealthsimple's estate review and planning process from the ground up, as the first person in this role — including how it integrates with our existing tax and family enterprise offerings
• Bring an AI-native mindset to the role — using AI tools to review documents faster, model scenarios, and raise the bar on what the team can deliver

What You Bring

• 5+ years of experience in estate planning, trusts and estates law, or a related wealth management advisory function
• A legal background, with hands-on experience reviewing or drafting wills, trusts, and related estate documents
• TEP designation strongly preferred
• Deep, demonstrated understanding of trusts — structures, taxation, and use cases across complex estates
• A solid working understanding of insurance policies and how to read them, with the ability to assess their role in an estate plan — note that this is not an insurance sales or advisory role
• Proven experience identifying gaps in existing estate plans and translating them into clear, actionable next steps for clients
• Excellent communication skills, with the ability to explain complex legal and estate concepts clearly to both advisors and clients
• Comfort operating without an established playbook — you'll be helping build the process, not just following one
• 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

• The rare opportunity to build a brand-new function from the ground up, not just fill an existing seat
• A purpose-driven role focused on client outcomes, not sales targets — you'll never be asked to sell a product
• 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, with the chance to shape a team as it scales
• Competitive salary and benefits package
• Be part of revolutionizing how estate planning is delivered as part of wealth management 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.
• Unlimited paid sick days, Wellness Days and the 90 day away program do not apply to certain roles.

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.

Compensation Range: CA$153.6K - CA$192K

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