Director, Advice Incubation & Experience

Wealthsimple Technologies

1d • Remote

About The Position

Wealthsimple is building the most sophisticated wealth platform in Canada — and we're just getting started. As Director of Advice Incubation & Experience, you will be the person who figures out what "premium" actually means for our clients and then goes and builds it.

Reporting to the VP of Wealth Management, this is a rare 0-to-1 role: part strategist, part builder, part entrepreneur. You won't be managing existing operations or defining core product features — you'll be designing and manually launching the next generation of high-touch advice experiences, proving they work, and handing off proven playbooks for our Service team to own and scale. You'll also be identifying and structuring the external partnerships that extend what Wealthsimple can offer to its most complex, high-net-worth clients.

This role lives at the intersection of service design, fintech 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?

Requirements

• 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 management and fintech landscape is evolving globally, with sharp instincts for what's a real shift versus noise
• Brings deep knowledge of what premium service actually feels like — from the client's perspective — and can translate that into a wealth management context
• Understands the difference between incubating a service and building a product — and is energized by the former
• Thinks commercially — you build beautiful experiences, but you always know what the business case is and how you'll prove it
• Is a natural lateral leader who can bring Sales, Service, Product, and Compliance together around a shared vision without direct authority over any of them
• Is tech-forward — comfortable using AI tools, low-code platforms, and lightweight scripting to build functional prototypes that test real concepts in market
• 7+ years of experience 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 platforms, or lightweight scripting — to rapidly prototype and test solutions
• Experience developing or managing strategic partnerships with external service providers
• Strong commercial instincts and the ability to design pilots that prove measurable ROI
• Experience working alongside scaled operational teams and transitioning V1 pilots into standardized, scalable 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 financial services 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

Responsibilities

• Define what "5-star" looks like in wealth management.
• Incubate and personally run new advice services.
• Stay ahead of where the industry is going.
• Build the partnerships that expand our offering.
• Arm our advisors and sales team with the tools to win.
• Prove commercial impact.

Benefits

• Top-tier health benefits and life insurance
• Long-term group savings with employer match using our Wealthsimple for Business platform
• 20 vacation days + 4 wellness days per year, and unlimited sick and mental health days
• 90 days away program: Employees can work outside of Canada for up to 90 days per calendar year
• A wide variety of peer and company-led Employee Resources Groups (e.g., Rainbow, Women of Wealthsimple, Black @ WS)

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed