Change Specialization Lead driving AI and ERP transformation strategies, commercialization, and adoption. Partnering with executive leaders to influence transformation and market growth.
About the role
- AI & CX Systems Director shaping customer experience through AI innovations at Wealthsimple. Leading technical teams to enhance operational strategies and deliver measurable outcomes.
Responsibilities
- 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
- 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
- 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
- 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
- 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
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
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
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