Wealthsimple Technologies - Manager, Systems Operations
Requirements
• What is the largest concurrent agent headcount you have supported in a single CX systems environment? • Under 500 agents • 500 - 999 agents • 1,000 - 1,999 agents • How many years of direct people management experience do you have specifically leading technical system administrators, operations specialists, or ICs? • Which of the following best describes your hands-on experience with Enterprise Zendesk (or equivalent Enterprise CX platforms like Salesforce Service Cloud)? • Administration (Managing agent provisioning, creating macros/shortcuts, building basic views, and pulling standard out-of-the-box reports.) • Standard Configuration (Building complex triggers and automations, managing multiple ticket forms/brands, mapping standard routing logic, and installing out-of-the-box marketplace apps.) • Enterprise Operations (Configuring Omnichannel/skill-based routing, setting up API webhooks to sync with external databases, managing Custom Objects, and running strict Sandbox-to-Production deployment cycles.) • Do you have direct experience managing the day-to-day operations (QA, hallucination mitigation, knowledge base tuning) of a generative AI bot in a live customer support environment? • Are you familiar with these Core CRM & Ticketing Platforms? • Zendesk (Enterprise) • Salesforce Service Cloud • Are you familiar with these Telephony & CCaaS solutions? • Have you supported any of these AI, Automation & Bot Platforms? • Are you legally eligible to work in Canada? • What is the location where you permanently reside? • Submit Application
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 • 🌎 We are a hybrid team with over 1,500 employees across North America. The people are one of the best parts of working here: you'll collaborate with incredibly talented, curious, and driven teammates who are deeply committed to doing great work. • Technology & Innovation at Wealthsimple: We move quickly and build thoughtfully. That means we're always looking for better ways to work — whether that's new tools, AI, or rethinking how we approach a problem. We don't expect you to have all the answers, but we do expect curiosity and a willingness to evolve alongside the products we're building. • Inclusion Statement: We're building products for a diverse world, and we need a diverse team to do it well. We strongly encourage applications from everyone, regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status. • Accessibility Statement: We're committed to an accessible hiring experience. If you need any accommodations throughout the interview process, please let us know — we'll work with you to make sure you have what you need. We also welcome any feedback on how we can better accommodate candidates with accessibility needs. • AI in Hiring: We may use artificial intelligence (AI) tools to support parts of our hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our team but don't replace human judgment – all final hiring decisions are made by people. If you have questions about how your data is used, reach out to us.
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