Director of Product, Wealthsimple
Customer Care & Artificial Intelligence
Professional investing services made simple
Job no longer available
Professional investing services made simple
1001+ employees
Job no longer available
1001+ employees
Company mission
To help everyone achieve financial freedom.
Role
Who you are
- 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
What the job involves
- 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
- 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
Our take
Wealthsimple is one of a crop of robo-advisors trying to democratize investment management. These companies are disrupting the industry by automating many of the processes involved in investment removing the need for human advisors.
But while other so-called robo-advisors are focused on courting the high end of the market, Wealthsimple is trying to provide the same types of tools and advice to all users, regardless of the amount they have to invest.
Wealthsimple does have higher fees than some other robo-advisors such as Betterment and Charles Schwab. However, the company believes that it provides a more user-friendly platform, tailored to millennials who will be attracted to Wealthsimple due to its ease of use and social impact offerings.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
-10% employee growth in 12 months
Company
Funding (last 2 of 9 rounds)
Oct 2025
$394m
LATE VC
May 2021
$537.2m
LATE VC
Total funding: $1.2bn
Company benefits
- Retirement savings matching plan through Wealthsimple Work
- Company equity for full-time employees
- Access to Premium Client perks, including personal finance learning & advice and a boosted interest rate on deposits
- Paid parental leave (6 months topped up to 100% of salary)
- 20 vacation days per year
- 90 Days Away program
- Top-tier health benefits
- Life & disability insurance
- Generous sick and mental health days
- Employee resource plan including services like RMT, psychology, and physiotherapy
- Up to $5,000 per year for mental health supports
- Gender Affirmation benefits
- Up to $1,500 per year for professional development
- Up to $1,500 per year for wellness and home office expenses
- Employee resource groups
- Social impact hours
Company HQ
Fashion District, Toronto, ON
Leadership
Michael Katchen
(CEO)Previously worked as a Business Analyst at McKinsey and then at Ancestry.com as Country Director for Canada.
Share this job
View 17 more jobs at Wealthsimple