Wealthsimple
Operations
Manager,SystemsOperations
Neural analysis suggests this role is
optimal for Senior candidates.
“Manager, Systems Operations at Wealthsimple. Skills: process management, cross-functional coordination, vendor/stakeholder management, operational metrics, resource planning, continuous improvement, CX Systems/Technical Operations, managing technical debt, mitigating AI hallucinations, AI agent health management, prompt tuning, knowledge base ingestion QA, regression testing for new AI releases, Jira request ingestion model, defining acceptance criteria, managing technical debt, enforcing CI/CD-”
What You'll Achieve.
Ensure the stability, routing logic, and API integrations across Zendesk and Five9 are running flawlessly for 2,000+ global agents; Manage bot QA, monitoring deflection rates, and troubleshooting integrated AI workflows; Deploying resources without burning out your team; Build, test, and deploy new telephony trees or AI workflows safely into production
Industry & Context.
mitigating AI hallucinations; triaging bugs; sizing M-level system enhancements; troubleshooting integrated AI workflows; seeing a queue of 600 quarterly support tickets as a math problem to be solved through better tooling, self-service, and root-cause fixes
What They're Looking For.
Must Have
5+ years in CX Systems/Technical Operations, 2+ years directly managing technical admins or systems engineers, Successfully managed infrastructure for 1,000+ agent environments, Expert-level administration of Enterprise Zendesk and CCaaS platforms, Deeply understand complex routing, custom objects, trigger/automation load balancing, and API webhook integrations, Proven experience running a sprint-based delivery model using Jira, Experience managing bot QA, monitoring deflection rates, and troubleshooting integrated AI workflows
Nice to Have
Five9 preferred, Experience in Fintech or a highly regulated security environment
What You'll Do.
Lead the day-to-day operations of a massive
heavily integrated CX ecosystem supporting 2
Run the team with the rigor of an engineering squad: owning sprint planning
Act as the ultimate escalation point for KTLO (Keep The Lights On) operations
and API integrations across Zendesk and Five9 are running flawlessly for 2
Oversee the day-to-day health of our AI agent
Handle 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 M-level system enhancements
and deploying resources without burning out the team
Work lockstep with our Strategy & Design architects to build
and deploy new telephony trees or AI workflows safely into production
How You'll Work.
Team & Collaboration
Manage a specialized team of Team Leads, Senior ICs, and Systems Admins; Work lockstep with our Strategy & Design architects
Process & Methodology
sprint planning, velocity tracking, backlog grooming, standups, sprint-based delivery model using Jira, defining acceptance criteria, managing technical debt, enforcing CI/CD-style deployment safety
Full Job Description
BUILD SOMETHING PEOPLE LOVE Wealthsimple's mission is to help everyone achieve financial freedom – by making financial services simple, transparent, and low-cost. We're Canada's largest fintech, trusted by over 3 million clients with more than $100 billion in assets. We move fast, we own our work, and we care deeply about the people using our products. If that sounds like you, keep reading. We're proud of what we've built — and we're just getting started. 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. 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
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