Manager, Systems Operations

Build something people love 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. We're proud of what we've built — and we're just getting started. Read our Culture Manual and learn more about how we work. The Systems Design & Optimization team is the technical backbone of Wealthsimple's CX Operations. We operate like an embedded engineering squad: we design the architecture, we build it, and we ensure it scales. As the Manager, Systems Operations, you are our execution engine. You will lead the day-to-day operations of a massive, heavily integrated CX ecosystem supporting 2,000+ agents. You aren't drafting the blue-sky vision; you are the operational general running agile sprints, managing technical debt, mitigating AI hallucinations, and keeping our platform highly available. The Stack: Zendesk (Enterprise), Five9, Decagon (GenAI), Jira, Atlassian Suite, REST APIs/Webhooks. What You’ll Do Manage a specialized team of Team Leads, Senior ICs, and Systems Admins. You will run this team with the rigor of an engineering squad: owning sprint planning, velocity tracking, backlog grooming, and standups. Act as the ultimate escalation point for KTLO (Keep The Lights On) operations. Ensure the stability, routing logic, and API integrations across Zendesk and Five9 are running flawlessly for 2,000+ global agents. Oversee the day-to-day health of our AI agent. Your team will handle rapid prompt tuning, hallucination mitigation, knowledge base ingestion QA, and regression testing for new AI releases. Your team receives 20+ complex Jira requests daily from CX leadership. You will own the ingestion model—triaging bugs, sizing M-level system enhancements, and deploying resources without burning out your team. Work lockstep with our Strategy & Design archi tects. When they design a new telephony tree or AI workflow, your team builds, tests, and deploys it safely into production. What You Bring 5+ years in CX Systems/Technical Operations, with 2+ years directly managing technical admins or systems engineers. You have successfully managed infrastructure for 1,000+ agent environments.