Manager, Systems Operations

Build something people love

Wealthsimple's mission is to help everyone achieve financial freedom – by making financial services simple, transparent, and low-cost. We're Canada's largest fintech, trusted by over 3 million clients with more than $100 billion in assets. We move fast, we own our work, and we care deeply about the people using our products. If that sounds like you, keep reading.

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 Client Experience Operations org. We own the platforms, tools, and infrastructure that power every client and agent interaction. We operate like a product and engineering team embedded in CX: we design what gets built, we build it, and we make sure it keeps working. The Systems Operations team is the execution engine of this model — the team that keeps the lights on, ships the work, and supports every agent in the org.

This role leads the team that keeps Wealthsimple's CX platform running day-to-day at a massive scale (2,000+ agents). You manage a team of specialists and team leads responsible for KTLO (keep the lights on) work, user support for our agent population, day-to-day AI operational maintenance, and the execution of M-size systems projects.

Think of this role like an Engineering Manager in a product org, you're running a sprint-based team against a prioritized backlog, keeping the on-call function healthy, and making sure your team is unblocked. The backlog you're executing against is shaped by the experience owners and architects; your job is to make sure it gets delivered reliably, with extreme operational rigor.

You'll manage three direct functions: a Team Lead for Decagon Operations (quality control, hallucination triage, release testing), a Team Lead for Agent Support (user troubleshooting, XS and S work), and a group of Senior ICs handling M-size systems admin work across Zendesk and Five9.

In this role you'll have the opportunity to:

• Lead and develop a high-performing systems operations team: Manage, coach, and develop a team of technical specialists and team leads. Set clear expectations, run effective sprint rituals, and create an environment where your team can do their best work.

• Own the execution of the systems backlog: Run a sprint-based delivery model against a prioritized backlog of systems work. Ensure tickets are triaged correctly, work is sized and assigned appropriately, and the team is shipping consistently against commitments.

• Own the enterprise agent support function: Your team is the first line of support for 2,000+ agents across the org. Own the model for how we triage, prioritize, and resolve user support requests — and maintain a high bar for response time and resolution quality.

• Maintain the health of AI (Decagon) operations: Through your Team Lead for Decagon Operations, ensure the day-to-day quality and reliability of our AI chat and voice experiences — handling hallucination fixes, knowledge base updates, quality control, and release testing.

• Partner with Strategy & Design: When an experience owner designs something, your team builds it. You're responsible for ensuring your team understands what's being asked, has the capacity to deliver it, and executes to the standard set by the design.

• Drive continuous improvement: The heavy operational load your team handles daily requires constant optimization. Own the model for how we track, triage, and reduce that volume over time through better tooling, self-service, and process rigor.

What you bring:

• 5+ years of experience in CX systems, support operations, or a related technical operations role, with at least 2 years of direct people management experience.

• Enterprise Scale: Proven experience managing CX systems for large organizations. (Experience supporting 1,000+ agents is highly preferred).

• Engineering Rigor: Experience running a team in an agile or sprint-based delivery model — you understand how to maintain a healthy Jira backlog, run sprint rituals, and keep a technical team focused.

• Deep System Knowledge: Strong technical grounding in enterprise CX platforms — heavily indexing on Zendesk and Five9 (or equivalent) — with the ability to understand and triage the full range of work your team handles.

• AI/Bot Operations: Familiarity with the operational realities of AI tools (like Decagon)—you understand what it takes to maintain, QA, and fix integrated AI experiences on a daily basis.

• Operational Mindset: A track record of building systems and processes that make a team more efficient over time, moving them from reactive firefighting to proactive management.

• Bonus: Fintech or regulated financial services experience.

Why Wealthsimple?

🌸 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.

ICYMI

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.