Director, AI & CX Systems

Wealthsimple Technologies

1d • Hybrid

About The Position

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 and learn more about how we work.
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.
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.
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.

Requirements

• 8–10+ years in CX systems, product management, platform design, or AI/automation strategy, with a track record of building and scaling technical solutions
• Proven people leadership: experience building and leading high-performing technical/product teams to deliver measurable outcomes
• Deep expertise in CX platforms and the tools that power modern support; paired with the imagination to look beyond them
• Hands-on experience with AI in customer-facing applications. You understand how agentic AI works: retrieval-augmented generation, automated procedures, prompt design, and how they combine to drive quality outcomes
• Systems thinking at your core: you see how knowledge structure impacts retrieval, how AI operating procedure design interacts with context, and how monitoring enables confident scaling
• Builder's mentality: you're comfortable designing workflows, writing requirements, analyzing data, and personally architecting solutions
• Strong technical fluency: you hold your own with engineers and data scientists in design conversations
• A pioneer's mindset: energized by ambiguity, excited to build what doesn't exist yet, passionate about AI as a transformational force in CX

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-service, and agent enablement
• Design knowledge architecture optimized for machine retrieval; understanding that KB structure directly impacts AI agent accuracy
• Build feedback loops that surface content gaps in real time and close the loop between AI performance and knowledge quality
• People Leadership
• Lead, coach, and develop high-performing teams across all three pillars
• Attract and grow top talent; build capabilities to keep pace with a rapidly evolving landscape
• Foster a culture of ownership, accountability, and continuous improvement

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 501-1,000 employees