Wealthsimple

Manager, Systems Operations

Wealthsimple • $100K — $130K *
US-AnywhereRemote in Canada
Consumer Technology
5 - 7 years of experience
3 weeks ago
Job Overview by Ladders

Qualifications

  • 5+ years in CX Systems/Technical Operations.
  • 2+ years of experience managing technical admins or systems engineers.
  • Expert-level administration of Enterprise Zendesk and CCaaS platforms (Five9 preferred).
  • Experience in sprint-based delivery using Jira, focusing on CI/CD safety.
  • Familiarity with operational management of GenAI systems.

Responsibilities

  • Lead a team of Team Leads, Senior ICs, and Systems Admins focused on sprint planning and backlog management.
  • Act as the escalation point for KTLO operations, ensuring stability across Zendesk and Five9.
  • Oversee daily health and performance of the AI agent, including prompt tuning and QA.
  • Manage the influx of complex requests from CX leadership, focusing on triaging and bug handling.
  • Collaborate with Strategy & Design architects to build, test, and deploy new workflows.

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.
  • Option to work outside Canada for up to 90 days per year.
  • Supportive employee resource groups, fostering diversity and inclusivity.
Full Job Description
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.

About Wealthsimple

Wealthsimple is a financial services company that provides online investment management and trading services. The company's platform allows users to invest in a variety of financial products, including stocks, bonds, and exchange-traded funds (ETFs), and offers a range of tools and resources to help users manage their investments. Wealthsimple also offers a high-interest savings account and a tax preparation service. The company was founded in 2014 and is headquartered in Toronto, Canada.
Learn more about Wealthsimple
Size
500 employees
Industry
Finance & Insurance
Founded
2014
* Ladders Estimates

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