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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 $125 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.

About the AI Products team

Our team, AI Products, is leading the AI effort across Wealthsimple. Setting the vision, building the intelligence layer, and experimenting with new ways the power of AI can shape the future of fintech to deliver better financial outcomes for our clients.

One of our primary focuses, and where this person will step in to lead, is building new client-facing experiences powered by AI. We believe these new capabilities will let us make Wealthsimple more proactive, more personalized, and fundamentally rethink how clients engage with us. That means reshaping both the in-app experience and interactions beyond the app itself. This is a true zero-to-one effort, and we're looking for someone who can lead and own it end to end.

What you’ll do

• Help define the product vision and strategy for a new set of client-facing AI experiences at Wealthsimple, and own the roadmap to bring them to life.

• Lead the planning, development, launch, and ongoing iteration of new AI-powered client experiences. Exploring what’s now possible and turning those possibilities into products clients truly value.

• Support a cross-functional team of engineers, designers, and data scientists as we collectively explore new ways of working.

• Partner with other product teams and departments across the company (e.g. Marketing, Operations, Customer Support, Legal and Compliance, and more) to build these new experiences.

• Help elevate the Product Management practice at Wealthsimple and create an inclusive and supportive team culture.

Skills you bring

• A multi-year track record of building and shipping products that customers love, and experience across both customer-facing and platform product management. You’ve owned a complete product or large parts of an offering and are comfortable leading large cross-functional projects with significant technical complexity (e.g., a system re-architecture, a major data migration, etc.).

• Experience working in a fast moving tech company.

• A shipping mentality. We don't believe in spending forever analyzing and debating. The best way to validate something is to ship it — so let's ship it, learn, and iterate.

• Enough technical know-how to talk with engineers about architecture and technical considerations that impact product, and a desire to learn what you don’t know to help drive decision making.

• A passion for financial inclusion and building products that increase access to financial freedom for everyone.

• Bonus: Experience building, shipping, iterating and growing products from 0 to 1 over multiple years. We know building new client experiences that client love will require a sustained multi-year effort.

Who you are

• A systems thinker that can distill many use-cases into a simple, elegant, generic logical solution design.

• A strong technical partner who is comfortable working with engineering to translate a logical system design into a technical architecture design.

• Able to navigate uncertainty and ambiguity and adept at synthesizing actionable problems, insights, and requirements from raw, unstructured qualitative and quantitative data.

• A thoughtful, critical thinker who follows a systematic and rigorous approach to problem solving.

• Scrappy and comfortable flexing into different roles to support your team. For example:

  • Business model and business case development

  • Workflow and operational process development

  • Negotiation with external vendors, regulatory bodies, and more

• An excellent communicator that can convey complex ideas succinctly and clearly.

• A naturally collaborative and empathetic leader; comfortable working with a diverse group of stakeholders, making sure every voice is heard.

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.