Director of Product, Customer Care & AI
Wealthsimple
Software Engineering, Product, Data Science, Customer Service
Remote
Posted on Oct 22, 2025
Your career is an investment that grows over time!
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 4 million users who trust us with more than $80 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.
About this Role
We’re looking for a Director of Product to lead the vision and strategy for how Wealthsimple delivers an exceptional customer support experience — one that feels effortless, human, and unmistakably Wealthsimple.
You’ll lead the product direction for our Customer Support and AI platforms, which power both client-facing and agent-facing experiences. This includes the customer facing AI chat and AI voice as well as our internal agent tools.
Your mission will be to make support radically more efficient and more delightful — by leveraging automation, generative AI, and exceptional product design. You’ll help Wealthsimple reduce average handle times, drive self-serve resolution, and enable our support team to scale without sacrificing empathy or quality.
You’ll report directly to the VP of Product, and partner closely with leaders across Engineering, CX, and AI Research to shape the future of AI-powered support at Wealthsimple.
In this role you’ll have the opportunity to:
- Own the product strategy for Wealthsimple’s customer support and AI platforms — ensuring we deliver fast, reliable, and high-quality help experiences for clients and agents alike
- Drive measurable outcomes like reducing ticket volume, improving first-contact resolution, and shortening average handle time through automation and smart tooling
- Develop and execute the roadmap** for internal agent platforms and client chat systems, building on Wealthsimple’s foundational LLM infrastructure
- Collaborate deeply with Engineering to create and scale shared capabilities — prompt orchestration, evaluation frameworks, observability, and compliance tooling — that other product teams can build on
- Partner with CX leadership to understand pain points, uncover automation opportunities, and ensure our products meaningfully improve both client and agent experiences
- Mentor and grow a team of PMs, helping them connect daily execution to long-term strategy
- Shape the narrative of AI at Wealthsimple, helping us define what “Wealthsimple-grade” AI feels like — helpful, transparent, and human
What you'll bring:
- You’ve built and scaled product experiences at the intersection of AI and customer experience, ideally in a fintech or consumer technology environment
- You have a track record of leading 0→1 and 1→n product development — from early experimentation to scaled systems used by thousands of clients or agents
- You combine strong product intuition with an analytical mindset; you care about both the quality of an experience and the measurable outcomes it drives
- You are a hands-on leader. You get into the weeds of whatever you do whether it’s customer support tickets, analyzing SQL data, writing LLM prompts, etc
- You’re comfortable operating in high-ambiguity environments — setting clear strategy, simplifying complex systems, and bringing cross-functional teams with you
- You’re deeply collaborative, empathetic, and low-ego — you believe the best work happens in partnership with engineering, design, and operations
- You’re curious about AI, stay close to advances in LLM applications, and have experience translating technical possibilities into practical product strategy
Why Wealthsimple?
🤑 Competitive salary with top-tier health benefits and life insurance
📈 Retirement savings matching plan using Wealthsimple for Business
🌴 20 vacation days per year and unlimited sick and mental health days
📚 Up to $1,500 per year towards wellness and professional development budgets respectively
🛫 90 days away program: Employees can work internationally in eligible countries for up to 90 days per calendar year
🌎 A wide variety of peer and company-led Employee Resource Groups (ie. Rainbow, Women of Wealthsimple, Black @ WS)
💖 Company-wide wellness days off scheduled throughout the year
We’re a remote-first team, with over 1,000 employees coast to coast in North America. Be a part of our Canadian success story and help shape the financial future of millions — join us!
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.
