Manager, Systems Operations

Wealthsimple is Canada’s leading financial innovator. The company offers a full suite of simple, sophisticated financial products across managed investing, do-it-yourself trading, cryptocurrency, tax filing, spending and saving. Wealthsimple currently serves more than 4 million Canadians and holds over $125 billion in assets under administration. The company was founded in 2014 by a team of financial experts and technology entrepreneurs, and is headquartered in Toronto, Canada.

We're proud of what we've built — and we're just getting started. Read our Culture Manual and learn more about how we work.

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 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.

What You Bring

• 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.

🌸 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.