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Wealthsimple, Canada's leading financial innovator serving 4+ million Canadians with $155B+ in assets under administration, is building a new Estate Planning function within its Wealth Management division. This is the first role of its kind at the company.
You will be the founding Estate Planning Specialist, responsible for designing and executing Wealthsimple's estate review and planning process for high-net-worth clients. Unlike traditional advisory roles, this is not a sales position—you'll focus entirely on client advocacy and outcomes.
Key responsibilities include:
- Reviewing clients' existing wills, trust documents, and broader estate plans to assess alignment with their goals
- Identifying gaps and misalignments in estate structures, articulating them clearly in plain language
- Laying out concrete next steps and connecting clients to appropriate resources (estate lawyers, documentation partners, etc.)
- Applying deep trust expertise to identify planning opportunities across complex, multi-entity estates
- Reviewing insurance policies as inputs to overall estate planning
- Acting as internal liaison to the Advisor team on complex estate cases
- Supporting client-facing conversations on sophisticated estate planning questions
- Designing Wealthsimple's estate review process from the ground up, including integration with tax and family enterprise offerings
- Leveraging AI tools to review documents faster, model scenarios, and enhance team capabilities
This role offers the rare opportunity to build a new function rather than fill an existing seat. You'll work with a fast-moving, ambitious team in a purpose-driven environment with no sales targets or commission structure. The company emphasizes an AI-native mindset and is committed to challenging industry norms.
Wealthsimple offers competitive benefits including top-tier health coverage, employer-matched savings, 20 vacation days plus 4 wellness days and unlimited sick/mental health days, 90 days annual work-from-anywhere flexibility, and employee resource groups. The team is hybrid with 1,500+ employees across North America.
REQUIREMENTS:
- 5+ years of experience in estate planning, trusts and estates law, or related wealth management advisory function
- Legal background with hands-on experience reviewing or drafting wills, trusts, and related estate documents
- TEP (Trust and Estate Practitioner) designation strongly preferred
- Deep, demonstrated understanding of trusts—structures, taxation, and use cases across complex estates
- Solid working understanding of insurance policies and ability to assess their role in estate plans
- Proven experience identifying gaps in existing estate plans and translating them into clear, actionable next steps
- Excellent communication skills; ability to explain complex legal and estate concepts clearly to advisors and clients
- Comfort operating without an established playbook; ability to help build processes from scratch
- Client-first mentality
- AI-native mindset and enthusiasm for using AI tools
- Bilingual (English/French) capability is a significant asset
