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Canada
Remote only
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 $169 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 a 0-to-1 role: part strategist, part builder, part entrepreneur, managing a small team. You'll design and launch the next generation of advice experiences, prove they work, and hand off proven playbooks to our sales and service teams to own and scale.
Your scope is the whole of Wealthsimple's advice business, not a single client segment. This role lives at the intersection of sales, service, product innovation, and commercial execution, and it exists to answer one question: what does a truly differentiated, human-centred advice experience look like at Wealthsimple, and how do we prove it works before we scale it?
Your Impact
Define what "5-star" client experiences look like in wealth management. Draw on deep knowledge of premium service (luxury hospitality, high-end retail, or elite financial services) to design client experiences that are differentiated. You'll set the bar for what every advice client can expect from Wealthsimple, and you'll do it by building real things with real clients.
Incubate and personally run new advice services. Take a concept, like a new advice offering, an estate concierge, or a high-touch onboarding experience, and figure out how to deliver the MVP before it's ready to be scaled. The innovation is in designing a client experience that is truly differentiated and, through the use of technology & AI, highly scalable. When it works, you package it into a playbook and hand it to sales or service teams to run at scale. You own the incubation and inform the scaled delivery.
Build the advisor tooling that makes advice better and faster. Work hand-in-hand with product teams and advisors to take advisor tooling from manual to automated. You set the requirements, translate advisor reality into product specs, and work with other leaders to drive adoption.
Stay ahead of where the industry is going. You're plugged into the evolving advice and wealth landscape, the startups, the disruptors, and the best incumbents globally. You bring that intelligence back and help us sharpen hypotheses about what to build next, complemented by a close read of what our own clients value and where they feel under-served.
Prove commercial impact. Every pilot is measured against clear metrics, AUM growth, conversion, and client satisfaction. You design experiments that prove value before we commit to scaling, and you make backed recommendations on what to accelerate, refine, or sunset.
What You'll Do
Work directly with and senior leadership to shape the future of Wealthsimple's advice offering
Launch and personally run the first iterations of services that will eventually reach hundreds of thousands of clients
Shape Wealthsimple's digital advice roadmap from the front line. Our advisors talk to clients every day, you turn what you hear into validated demand signals for product teams.
We're Looking for Someone Who
Is energized by the messy, creative, manual work of building something from nothing, and doesn't need a large team or perfect infrastructure to get a pilot off the ground
Has a genuine obsession with how the wealth and fintech landscape is evolving globally, with sharp instincts for real shift versus noise
Brings deep knowledge of what premium service actually feels like from a client's perspective, and can translate it into a wealth management context
Thinks commercially: you build experiences, but you always know the business case and how you'll prove it
Is a natural leader who can bring stakeholders together around a shared vision
Is tech-forward: comfortable with AI tools, low-code platforms, and lightweight scripting to build functional prototypes that test real concepts in market
Is the person who notices the detail nobody asked for, and arrives with ideas about what would make a client tell their friends about us
What You'll Bring
5-7+ years in service design, strategy, innovation, or premium client experience (ideally with exposure to HNW or complex client segments)
A proven track record of taking a service concept from idea to live pilot (true 0-to-1 experience)
Demonstrated ability to use modern technology, AI tools, low-code/no-code, or lightweight scripting, to rapidly prototype and test
Experience working alongside scaled operational teams and transitioning pilots into standardized processes, with a clear ability to hand off and let go
Familiarity with the wealth management landscape: how different advice models work, what HNW clients value, and how firms grow AUM
Comfort working in regulated environments and partnering with compliance teams
Outstanding communication skills: you can influence executives, inspire advisors, and earn the trust of external partners
🌸 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.
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.
