Wealthsimple

Director, Client Experience Systems Architecture

Remote (Canada) · Director

Sponsorship not specifiedDetected 19 days ago

LLMsRAGAgentic AIAccessibilityAgileCRM

About the role

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.
We're proud of what we've built - and we're just getting started.

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.
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.
Technology & Innovation at Wealthsimple: We move quickly and build thoughtfully.
We don't expect you to have all the answers, but we do expect curiosity and a willingness to evolve alongside the products we're building.
Inclusion Statement: We're building products for a diverse world, and we need a diverse team to do it well.
AI in Hiring: We may use artificial intelligence (AI) tools to support parts of our hiring process, such as reviewing applications, analyzing resumes, or assessing responses.
you'll collaborate with incredibly talented, curious, and driven teammates who are deeply committed to doing great work.
You hold your own with engineers and data scientists.
You have built teams, but you also dive into the weeds of process mapping and system design when the team is stuck.

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.
If you have questions about how your data is used, reach out to us.
Design and oversee the holistic tech stack required to serve millions of clients and thousands of agents.
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.
You can clearly articulate the capabilities and components a 2,000-agent organization needs.
8-10+ years in CX systems, technical product management, and/or AI architecture.
You know how to make AI take action securely.
You know the players, the hype, and the architectural trade-offs of using them.

🌴 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

🌸 Top-tier health benefits and life insurance
We strongly encourage applications from everyone, regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.

The company was founded in 2014 by a team of financial experts and technology entrepreneurs, and is headquartered in Toronto, Canada.
Read our Culture Manual https://www.wealthsimple.com/en-ca/culture and learn more about how we work https://www.wealthsimple.com/en-ca/careers.
We're looking for a highly technical, systems-oriented leader to architect the future of how technology powers exceptional customer experiences at scale.
🌎 We are a hybrid team with over 1,500 employees across North America.

This listing is sourced directly from Wealthsimple's careers page and normalized into a canonical job model.