Top Benefits
Retirement savings match
Company equity
Top-tier health benefits
About the 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
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
Top Benefits
Retirement savings match
Company equity
Top-tier health benefits
About the 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
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