Director of Digital Advice
Wealthsimple
Remote
Posted on Jan 28, 2026
Build something people love
Wealthsimple is on a mission to help everyone achieve financial freedom by reimagining what it means to manage your money. Using smart technology, we take financial services that are often confusing, opaque and expensive and make them transparent and low-cost for everyone. We’re the largest fintech company in Canada, with over 3+ million users who trust us with more than $100 billion in assets.
Our teams ship often and make an impact with groundbreaking ideas. We're looking for talented people who keep it simple and value collaboration and humility as we continue to create inclusive and high-performing teams where people can be inspired to do their best work.
Role Overview
As the Director of Digital Advice at Wealthsimple, you will shape the future of how we deliver personalized financial guidance at scale. Reporting to the VP of Wealth Management, you'll lead the strategic vision for our digital advice offerings to create transformative financial experiences for our 3+ million clients.
Your Impact
· Drive Digital Advice Strategy: Develop and implement a multi-year roadmap for Wealthsimple's digital advice offerings that significantly enhances client value and drives asset growthLead
· Innovation: Identify and execute on the next 5 major bets in digital financial advice that will differentiate Wealthsimple in the market
· Deliver Scalable Guidance: Transform how we provide investment advice and financial planning through digital channels to reach more clients effectively
· Bridge Investment Expertise and Technology: Work collaboratively with product and tech teams to translate investment philosophy into engaging digital experiences
In this role, you will have the opportunity to:
- Collaborate with the VP of Wealth Management and Product leaders to develop and execute a transformative digital advice strategy
- Identify emerging technologies and approaches to deliver personalized financial guidance at scale
- Partner cross-functionally with marketing, sales, and product teams to create cohesive digital advice journeys
- Translate client needs and market opportunities into innovative digital advice solutions
- Drive growth in net deposits and assets under management through superior digital engagement
We're looking for someone who:
- Is passionate about revolutionizing how financial advice is delivered digitally
- Has a proven track record scaling digital advice offerings at a fintech or wealth management firm
- Thrives in fast-paced environments and enjoys cross-functional collaboration
- Actively tracks and possesses deep knowledge of emerging trends in investing and financial planning, leveraging a robust network of industry contacts and relationships.
- Can balance regulatory requirements with pushing boundaries in digital advice delivery
- Is energized by the opportunity to shape the future of digital wealth management
What You’ll Bring:
- 8+ years experience in the investment industry, with significant focus on building digital products in the wealth management industry - ideally digital advice offerings
- Demonstrated success developing and implementing digital advice strategies that drove user engagement and AUM growth
- Strong understanding of how technology enhances investment advice delivery and client outcomes
- Experience working with product teams to translate financial concepts into engaging digital experiences
- Ability to identify emerging trends in digital wealth management and translate them into actionable strategies
- Outstanding leadership skills with a track record of building and developing high-performing teams
- Exceptional communication abilities with the capacity to influence across technical and non-technical audiences
- 3-5 years leading small, high-impact teams or emphasizing experience building 0-to-1 initiatives with lean teams
- Experience building digital products or scaled solutions in wealth management, fintech, or adjacent industries, with deep understanding of investment advice delivery.
Why Wealthsimple?
🤑 Competitive salary with 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)
🌎 We’re a remote first team with over 1,500 employees across North America - and one of the best things about working here is the people. You’ll be collaborating with incredibly talented, curious, and driven teammates who care deeply about doing great work.
Technology & Innovation at Wealthsimple
We believe the future belongs to those who innovate boldly. At Wealthsimple, every team member is expected to lean into new technologies, including AI, and tooling to rethink how we work, solve problems faster, and create even greater value. We're looking for people who are not just comfortable with change but energized by it. Our commitment is to build a company that evolves at the pace of the world around us, and we want you to help lead that future.
DEI Statement
At Wealthsimple, we are building products for a diverse world and we need a diverse team to do that successfully. We strongly encourage applications from everyone regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.
Accessibility Statement
Wealthsimple provides an accessible candidate experience. If you need any accommodations or adjustments throughout the interview process and beyond, please let us know, and we will work with you to provide the necessary support and make reasonable accommodations to facilitate your participation. We are continuously working to improve our accessibility practices and welcome any feedback or suggestions on how we can better accommodate candidates with accessibility needs.
