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Manager, Systems Operations
Full-time
Wealthsimple is Canada's leading financial innovator, offering 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 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 — 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, running the team with the rigor of an engineering squad: sprint planning, velocity tracking, backlog grooming, and standups
Act as the ultimate escalation point for Keep The Lights On operations, ensuring stability, routing logic, and API integrations across Zendesk and Five9 run flawlessly for 2,000+ global agents
Oversee the day-to-day health of the AI agent: rapid prompt tuning, hallucination mitigation, knowledge base ingestion QA, and regression testing for new AI releases
Own the ingestion model for 20+ complex Jira requests daily from CX leadership — triaging bugs, sizing system enhancements, and deploying resources without burning out your team
Work lockstep with Strategy & Design architects: 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, and experience managing infrastructure for 1,000+ agent environments
Expert-level administration of Enterprise Zendesk and CCaaS platforms (Five9 preferred), with deep understanding of complex routing, custom objects, trigger/automation load balancing, and API webhook integrations
Proven experience running a sprint-based delivery model using Jira, defining acceptance criteria, managing technical debt, and enforcing CI/CD-style deployment safety in a live CX environment
Experience managing bot QA, monitoring deflection rates, and troubleshooting integrated AI workflows
A relentless optimizer mindset: you see a queue of 600 quarterly support tickets as a math problem to be solved through better tooling, self-service, and root-cause fixes
Bonus: experience in Fintech or a highly regulated security environment
Why Wealthsimple?
Top-tier health benefits and life insurance
Long-term group savings with employer match
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
A hybrid team of over 1,500 employees across North America
