Manager, Systems Operations
About The Position
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.
Requirements
- 5+ years in CX Systems/Technical Operations, with 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 (Five9 preferred).
- Deeply understand complex routing, custom objects, trigger/automation load balancing, and API webhook integrations.
- Proven experience running a sprint-based delivery model using Jira.
- Know how to define acceptance criteria, manage technical debt, and enforce CI/CD-style deployment safety in a live CX environment.
- Understand the unsexy, operational side of GenAI.
- Experience managing bot QA, monitoring deflection rates, and troubleshooting integrated AI workflows.
- 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.
Nice To Haves
- Experience in Fintech or a highly regulated security environment.
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.
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
Stand Out From the Crowd
Upload your resume and get instant feedback on how well it matches this job.
What This Job Offers
Job Type
Full-time
Career Level
Manager
Education Level
No Education Listed
