Estate Planning Specialist, Wealth Management

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.

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This is the first role of its kind  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.

• 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

• 5+ years of experience in estate planning, trusts…