• 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
• 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

• Retirement savings matching plan through Wealthsimple Work
• Company equity for full-time employees
• Access to Premium Client perks, including personal finance learning & advice and a boosted interest rate on deposits
• Paid parental leave (6 months topped up to 100% of salary)
• 20 vacation days per year
• 90 Days Away program
• Top-tier health benefits
• Life & disability insurance
• Generous sick and mental health days
• Up to $5,000 per year for mental health supports
• Gender Affirmation benefits
• Employee resource plan including services like RMT, psychology, and physiotherapy
• Up to $1,500 per year for professional development
• Up to $1,500 per year for wellness and home office expenses
• Employee resource groups
• Social impact hours- 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
• 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
• BONUS: Experience in Fintech or a highly regulated security environment
• 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
• 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