VP driving product - led growth and market activation for AI solutions in healthcare. Leading teams to enhance product adoption and customer engagement while ensuring strategic alignment and sustained 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
Job title
Job type
Experience level
Salary
Not specified
Degree requirement
Location requirements
Report this job
Found something wrong with the page? Please let us know by submitting a report below.
Operations Manager enhancing operational processes and systems for Big Viking Games, a Canadian gaming company. Focused on improving workflows and implementing AI in daily operations.
Director leading Cint’s enterprise AI transformation office driving measurable business value. Overseeing AI strategy and roadmap while managing high - impact teams and complex workflows.
Director of Enterprise AI Transformation at Cint leading AI - enabled operational change. Focused on measurable business value and managing AI transformation portfolio.
Director of AI Transformation leading enterprise AI initiatives at Cint to drive operational change and measurable business value. Collaborating with global teams to optimize AI workflows and governance frameworks.
AI Governance Advisor at Mila responsible for developing governance training programs and facilitating community of practice. Engaging with executive audiences in workshops and tailored programs.
Senior Cloud & AI Administrator responsible for Azure and Microsoft 365 services, implementing AI solutions. Ensuring security, scalability, modernization, and business outcomes through hands - on delivery.
Executive leader transforming ABC Fitness's Customer Support leveraging AI and new operational strategies. Responsible for driving enterprise - wide change and overseeing customer experience enhancements.
Bilingual AI Training & Business Transformation Specialist teaching AI training sessions for students and employers. Leading facilitation of hands - on AI projects and coaching in a remote setting.
AI Consultant/Freelancer supporting two AI pilots for learning programs at Venture for Canada. Providing strategic AI guidance and implementation support in a nonprofit context.