Wealthsimple

Director, Client Experience Systems Architecture

Wealthsimple • $130K — $180K *
US-AnywhereRemote in Canada
Enterprise Technology
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 8-10+ years in CX systems, technical product management, or AI architecture.
  • Proven experience building and leading high-performing teams.
  • Deep understanding of generative AI and related technologies like RAG and prompt engineering.
  • Familiarity with third-party CX AI vendor landscape and their architectural implications.
  • Ability to articulate complex systems design to both technical and non-technical stakeholders.

Responsibilities

  • Design and oversee the technology stack for client and agent services.
  • Collaborate with R&D and Engineering on AI agent integration and decision-making processes.
  • Create a knowledge ecosystem optimized for AI-driven retrieval and evaluation frameworks.
  • Structure team and processes based on operational data for prioritizing initiatives.
  • Lead discussions on CX AI trade-offs, guiding integrative efforts with managers.

Benefits

  • Top-tier health benefits and life insurance.
  • Long-term group savings with employer match via Wealthsimple for Business.
  • Generous vacation policy including 20 vacation days and 4 wellness days per year.
  • Opportunity to work outside Canada for up to 90 days annually.
  • Inclusive employee resource groups promoting diversity.
Full Job Description
Build something people love

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.

Key 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.


What You'll Bring:
  • 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.


Why Wealthsimple?

🌸 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

We are a hybrid team with over 1,500 employees across North America. 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.

ICYMI

Technology & Innovation at Wealthsimple: We move quickly and build thoughtfully. That means we're always looking for better ways to work - whether that's new tools, AI, or rethinking how we approach a problem. 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.

About Wealthsimple

Wealthsimple is a financial services company that provides online investment management and trading services. The company's platform allows users to invest in a variety of financial products, including stocks, bonds, and exchange-traded funds (ETFs), and offers a range of tools and resources to help users manage their investments. Wealthsimple also offers a high-interest savings account and a tax preparation service. The company was founded in 2014 and is headquartered in Toronto, Canada.
Learn more about Wealthsimple
Size
500 employees
Industry
Founded
2014

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