Manager, Systems Operations
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Job Description
Manager of Systems Operations at Wealthsimple leading technical operations for a large CX team. Responsible for ensuring stability and efficiency in a heavily integrated CX ecosystem.
Responsibilities:
- 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 architects. When they design a new telephony tree or AI workflow, your team builds, tests, and deploys it safely into production.
Requirements:
- 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.
- Expert-level administration of Enterprise Zendesk and CCaaS platforms (Five9 preferred). You deeply understand complex routing, custom objects, trigger/automation load balancing, and API webhook integrations.
- Proven experience running a sprint-based delivery model using Jira. You know how to define acceptance criteria, manage technical debt, and enforce CI/CD-style deployment safety in a live CX environment.
- You understand the unsexy, operational side of GenAI. You have experience managing bot QA, monitoring deflection rates, and troubleshooting integrated AI workflows.
- You are a relentless optimizer. 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.
Benefits:
- 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
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