Wealthsimple is a Toronto-based digital money management platform offering investing, trading, crypto, tax, spending and savings products to Canadian consumers.
BUILD SOMETHING PEOPLE LOVE Wealthsimple is Canada’s leading financial innovator. The company offers a full suite of simple, sophisticated financial products across managed investing, do-it-yourself trading, cryptocurrency, tax filing, spending and saving. Wealthsimple currently serves more than 4 million Canadians and holds over $155 billion in assets under administration. The company was founded in 2014 by a team of financial experts and technology entrepreneurs, and is headquartered in Toronto, Canada. We're proud of what we've built — and we're just getting started. Read our Culture Manual https://www.wealthsimple.com/en-ca/culture and learn more about how we work https://www.wealthsimple.com/en-ca/careers. We're looking for a highly technical, systems-oriented leader to architect the future of how technology powers exceptional customer experiences at scale. As the Director of CX Systems Architecture, you won’t just set a high-level vision, you will actively design the platform ecosystem, intelligence layer, and data infrastructure that enables millions of increasingly autonomous customer interactions. You are the definitive architect of our CX Operations stack. You will lead and scale three distinct, high-performing pillars: Systems Design, Knowledge & Content and AI Experiences. But you won't just manage the roadmap; you will get into the weeds. You must possess the deep technical acumen required to debate API payloads, map complex data flows, and design rigorous LLM evaluation loops directly with our Director of Engineering. Key Responsibilities: - Design and oversee the holistic tech stack required to serve millions of clients and thousands of agents. You must intimately understand how CRM, telephony, ticketing, content/knowledge bases, and agent interfaces seamlessly integrate. - Partner directly with R&D and Engineering to define how AI agents interact with internal APIs. Own the technical trade-offs of building in-house vs. buying third-party, and design the logic for agent routing, human handoffs, and escalations. - Reimagine Information Architecture. Design a knowledge ecosystem optimized for machine retrieval (RAG, semantic search, vectorization) and build the evaluation frameworks (LLM-as-a-judge, human-in-the-loop) that eliminate hallucinations. - Structure your team and intake processes to ruthlessly prioritize initiatives based on operational data. Bridge the gap between CX Operations and Engineering to ensure fast, agile delivery. - Be the definitive voice on CX AI trade-offs. You don’t need to write the production code, but you must be able to draw the system architecture on a whiteboard, define the edge cases, and guide your managers through complex integrations. What You'll Bring: - You can clearly articulate the capabilities and components a 2,000-agent organization needs. You hold your own with engineers and data scientists. - 8–10+ years in CX systems, technical product management, and/or AI architecture. You have built teams, but you also dive into the weeds of process mapping and system design when the team is stuck. - Deep, hands-on understanding of generative AI, RAG, prompt engineering, and Model Context Protocols (MCP). You know how to make AI take action securely. - Strong familiarity with the third-party CX AI vendor landscape. You know the players, the hype, and the architectural trade-offs of using them. WHY WEALTHSIMPLE? 🌸 Top-tier health benefits and life insurance 📈 Long-term group savings with employer match, through Wealthsimple for Business 🌴 20 vacation days, 4 wellness days, and unlimited sick and mental health days per year ✈️ 90 days away: work outside Canada for up to 90 days per year 👥 Employee resource groups, including Rainbow (2SLGBTQ), Women of WS, and Black at WS 🌎 We are a hybrid team with over 1,500 employees across North America. The people are one of the best parts of working here: you'll collaborate with incredibly talented, curious, and driven teammates who are deeply committed to doing great work. ICYMI Technology & Innovation at Wealthsimple: We move quickly and build thoughtfully. That means we're always looking for better ways to work — whether that's new tools, AI, or rethinking how we approach a problem. We don't expect you to have all the answers, but we do expect curiosity and a willingness to evolve alongside the products we're building. Inclusion Statement: We're building products for a diverse world, and we need a diverse team to do it well. We strongly encourage applications from everyone, regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status. Accessibility Statement: We're committed to an accessible hiring experience. If you need any accommodations throughout the interview process, please let us know — we'll work with you to make sure you have what you need. We also welcome any feedback on how we can better accommodate candidates with accessibility needs. AI in Hiring: We may use artificial intelligence (AI) tools to support parts of our hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our team but don't replace human judgment – all final hiring decisions are made by people. If you have questions about how your data is used, reach out to us.