[Hiring] Estate Planning Specialist @Wealthsimple Technologies

Role Description

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. 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 misalignments with clients' actual goals and explain what needs to change.
• Connect clients to the right resources to solve identified gaps.
• Help design and build the estate review and planning process itself.

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

Qualifications

• 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 understanding of trusts — structures, taxation, and use cases across complex estates.
• Solid working understanding of insurance policies and their role in an estate plan.
• 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.
• Comfort operating without an established playbook.
• A client-first mentality in everything you do.
• An AI-native mindset and enthusiasm for using AI tools.
• Bilingual (English/French) capability is a significant asset.

Requirements

• Review clients' existing wills, trust documents, and broader estate plans to assess their alignment with client goals.
• Clearly articulate misalignments in plain language and specify necessary changes.
• Lay out concrete next steps for clients and connect them to appropriate resources.
• Apply a deep understanding of trusts to identify planning opportunities across complex estates.
• Review existing insurance policies as part of the overall estate plan.
• Act as the internal liaison to the Advisor team on complex estate planning cases.
• Support client-facing conversations on sophisticated estate planning questions.
• Help design and build Wealthsimple's estate review and planning process.
• Utilize AI tools to review documents faster and model scenarios.

Benefits

• 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.
• 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.