Director, AI & CX Systems

Director, AI & CX Systems BUILD SOMETHING PEOPLE LOVE Wealthsimple's mission is to help everyone achieve financial freedom – by making financial services simple, transparent, and low-cost. We're Canada's largest fintech, trusted by over 3 million clients with more than $100 billion in assets. We move fast, we own our work, and we care deeply about the people using our products. If that sounds like you, keep reading. 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 systems-oriented, AI-forward leader to invent the future of how technology powers exceptional customer experiences at scale. As Leader of AI & CXO (Client Experience Operations) Systems, you'll own the platforms, intelligence layer, and content ecosystem that enable millions of customer interactions; designing and building the infrastructure that makes complex support simple, efficient, and increasingly autonomous. The Role: - This isn't about optimizing what exists today. - We want someone who thinks without constraints; who can look at the CX landscape, imagine what's possible with AI, and build toward it. - You won't be bound by current tools, platforms, or paradigms. - Your mandate is to define what world-class AI-powered customer experience looks like and then make it real. The Context: - Reporting to the VP of Client Experience Operations with a dotted line into the VP of Product, you'll lead high-performing teams aligned to three pillars (CXO Platform, AI Product, and Knowledge Systems) while partnering directly with the Director of Engineering on AI agent strategy and systems architecture. - You'll be the Ops counterpart to Engineering: together, you own the strategy that drives containment, accuracy, and quality (and the systematic execution that delivers it). - This means you'll be deep in the details of how our AI agent system works and how knowledge base structure, AI operating procedures, and contextual inputs combine to drive outcomes, while simultaneously leading teams and setting strategic direction. KEY RESPONSIBILITIES INVENT THE FUTURE OF AI-POWERED CX - Define a bold vision for how AI transforms customer experience at Wealthsimple: unconstrained by today's tools, vendors, or workflows - Stay at the frontier of generative AI, agentic frameworks, and automation technologies; rapidly deploy innovations that deliver value - Challenge assumptions, propose new paradigms, and be a recognized leader in AI-driven CX AI AGENT STRATEGY AND SYSTEMS ARCHITECTURE - Partner directly with the Director of Engineering to define and execute AI agent strategy - Own containment and accuracy/quality as primary metrics, and the holistic strategy that delivers them: architecting how Knowledge base, AI operating procedures, guidelines, and context work together as an integrated system - Establish systematic development practices: eval-driven development, simulation-based validation, A/B testing, continuous monitoring, and regression testing - Build the playbook for scaling AI agent coverage: diagnose with data, design with confidence, validate before deploying, monitor continuously - Coordinate all contributors to AI agent performance under a unified strategy, ensuring coherence across the system - Define the roadmap for expanding AI capabilities across the full customer journey PLATFORM STRATEGY & DESIGN - Lead the evolution of CX platform architecture: not just optimizing current systems, but envisioning and building what comes next - Design integrations, workflows, automations, and intelligent routing that create seamless, AI-powered experiences across channels - Drive interoperability across CXO and partner teams (e.g., Commercial), reducing manual handoffs and eliminating data silos KNOWLEDGE OPERATIONS & SYSTEMS - Reimagine how content fuels AI systems, self ... (truncated, view full listing at source)