Wealthsimple

Director, AI & CX Systems

Wealthsimple

full-time

Posted on:

Location Type: Remote

Location: Canada

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Job Level

Lead

About the role

  • 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
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
AIautomation technologiesgenerative AIA/B testingsimulation-based validationdata analysisworkflow designknowledge architectureagentic AIretrieval-augmented generation
Soft Skills
leadershipcoachingteam developmentstrategic thinkingproblem-solvingcreativityaccountabilitycontinuous improvementcommunicationcollaboration