About this RoleWe’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 alikeDrive measurable outcomes like reducing ticket volume, improving first-contact resolution, and shortening average handle time through automation and smart toolingDevelop and execute the roadmap for internal agent platforms and client chat systems, building on Wealthsimple’s foundational LLM infrastructureCollaborate deeply with Engineering to create and scale shared capabilities — prompt orchestration, evaluation frameworks, observability, and compliance tooling — that other product teams can build onPartner with CX leadership to understand pain points, uncover automation opportunities, and ensure our products meaningfully improve both client and agent experiencesMentor and grow a team of PMs, helping them connect daily execution to long-term strategyShape the narrative of AI at Wealthsimple, helping us define what “Wealthsimple-grade” AI feels like — helpful, transparent, and humanWhat 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 environmentYou 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 agentsYou combine strong product intuition with an analytical mindset; you care about both the quality of an experience and the measurable outcomes it drivesYou 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, etcYou’re comfortable operating in high-ambiguity environments — setting clear strategy, simplifying complex systems, and bringing cross-functional teams with youYou’re deeply collaborative, empathetic, and low-ego — you believe the best work happens in partnership with engineering, design, and operationsYou’re curious about AI, stay close to advances in LLM applications, and have experience translating technical possibilities into practical product strategyWhy 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 yearWe’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!Read our
Culture Manual and learn more about
how we work.Technology & Innovation at WealthsimpleWe 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 StatementAt 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 StatementWealthsimple 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. AI disclaimerWe may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.
