Senior Associate, Technical Operations

Location: Remote (Canada) Workplace: Remote BUILD SOMETHING PEOPLE LOVE 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 $155 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 https://www.wealthsimple.com/en-ca/culture and learn more about how we work https://www.wealthsimple.com/en-ca/careers. We are looking for a Senior Associate, Technical Operations to act as a hands-on workflow builder and quality owner within our Operations ecosystem. You will not just analyze bottlenecks, you will actively build, test, and maintain automated workflows that power our AI Chat Platform. You will bring a rigorous QA mindset to operational workflows: designing resilient logic, catching edge cases, monitoring failure queues, and deprecating outdated processes before they create friction. If you are a structured problem solver who loves writing clean SQL, automating workflows via orchestration tools and Python, and treating operational pipelines with engineering-grade quality standards, this role is for you. What You’ll Do - Build & Orchestrate Workflows: Design, configure, and maintain automated operational workflows using orchestration platforms (such as n8n or Workato) and custom scripting. - Own Workflow QA & Lifecycle Hygiene: Apply software QA discipline to operational systems. Define test cases, validate release readiness, monitor regression risks, and systematically "unship" or refactor legacy workflows that no longer serve the ecosystem. - Investigate & Optimize Pipeline Data: Dig into raw logs and database tables using advanced SQL and Python to identify failure patterns, isolate edge cases, and execute root-cause fixes on failed transactions. - Leverage Applied AI Pragmatically: Actively utilize modern LLM tools for structured data parsing, regex generation, error-log classification, and accelerating operational investigation. - Bridge Ops and Architecture: Partner closely with senior engineering and operational stakeholders to translate complex process requirements into scalable technical implementations. Challenge existing processes with data-backed technical arguments. What You Bring - 1–3+ Years of Relevant Technical Experience: Background in Technical Operations, Systems Analysis, Data QA, Software QA, or Workflow Automation where you were directly responsible for building, troubleshooting, and maintaining data-driven processes. - Solid Data Literacy (SQL & Scripting): Demonstrated ability to write performant SQL beyond basic queries (experience with CTEs, window functions, and query optimization). Foundational familiarity with Python or scripting for data manipulation. - Workflow Automation Mindset: Practical experience working with workflow engines, API integrations, or orchestration platforms (e.g., n8n, Workato, Make, Retool, or equivalent native workflow tools). - Engineering-Minded QA Instincts: You understand that shipping a workflow is only half the job. You instinctively think about edge-case handling, monitoring, rollback plans, and system dependencies. - Applied AI Fluency: You go beyond using LLMs for writing copy; you leverage AI tools to parse unstructured error strings, structure disparate datasets, and validate logic. - Clear Technical Communication: Able to engage deeply with software engineers on architecture while clearly explaining operational impacts to business partners. 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. *Unlimited paid sick days, Wellness Days and the 90 day away program do not apply to certain roles. 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.