Director, Client Experience Systems Architecture

Wealthsimple Technologies • ,

8d • Hybrid

About The Position

Wealthsimple is Canada’s leading financial innovator. The company offers a full suite of simple, sophisticated financial products across managed investing, do-it-yourself trading, cryptocurrency, tax filing, spending and saving. Wealthsimple currently serves more than 4 million Canadians and holds over $125 billion in assets under administration. The company was founded in 2014 by a team of financial experts and technology entrepreneurs, and is headquartered in Toronto, Canada.
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We're looking for a highly technical, systems-oriented leader to architect the future of how technology powers exceptional customer experiences at scale. As the Director of CX Systems Architecture, you won’t just set a high-level vision, you will actively design the platform ecosystem, intelligence layer, and data infrastructure that enables millions of increasingly autonomous customer interactions.
You are the definitive architect of our CX Operations stack. You will lead and scale three distinct, high-performing pillars: Systems Design, Knowledge & Content and AI Experiences. But you won't just manage the roadmap; you will get into the weeds. You must possess the deep technical acumen required to debate API payloads, map complex data flows, and design rigorous LLM evaluation loops directly with our Director of Engineering.

Requirements

• You can clearly articulate the capabilities and components a 2,000-agent organization needs. You hold your own with engineers and data scientists.
• 8–10+ years in CX systems, technical product management, and/or AI architecture. You have built teams, but you also dive into the weeds of process mapping and system design when the team is stuck.
• Deep, hands-on understanding of generative AI, RAG, prompt engineering, and Model Context Protocols (MCP). You know how to make AI take action securely.
• Strong familiarity with the third-party CX AI vendor landscape. You know the players, the hype, and the architectural trade-offs of using them.

Responsibilities

• Design and oversee the holistic tech stack required to serve millions of clients and thousands of agents. You must intimately understand how CRM, telephony, ticketing, content/knowledge bases, and agent interfaces seamlessly integrate.
• Partner directly with R&D and Engineering to define how AI agents interact with internal APIs. Own the technical trade-offs of building in-house vs. buying third-party, and design the logic for agent routing, human handoffs, and escalations.
• Reimagine Information Architecture. Design a knowledge ecosystem optimized for machine retrieval (RAG, semantic search, vectorization) and build the evaluation frameworks (LLM-as-a-judge, human-in-the-loop) that eliminate hallucinations.
• Structure your team and intake processes to ruthlessly prioritize initiatives based on operational data. Bridge the gap between CX Operations and Engineering to ensure fast, agile delivery.
• Be the definitive voice on CX AI trade-offs. You don’t need to write the production code, but you must be able to draw the system architecture on a whiteboard, define the edge cases, and guide your managers through complex integrations.

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

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed