Technical Operations specialist building and QA-testing automated AI chat workflows at Wealthsimple, Canada’s financial innovator. Using SQL, Python, orchestration tools, and LLMs to improve operational reliability.
Responsibilities
Act as a hands-on workflow builder and quality owner within the Operations ecosystem
Design, configure, and maintain automated operational workflows using orchestration platforms and custom scripting
Define test cases, validate release readiness, monitor regression risks, and refactor or deprecate legacy workflows
Investigate raw logs and database tables using advanced SQL and Python
Identify failure patterns, isolate edge cases, and execute root-cause fixes on failed transactions
Use modern LLM tools for structured data parsing, regex generation, error-log classification, and operational investigation
Partner with senior engineering and operational stakeholders to translate process requirements into scalable technical implementations
Challenge existing processes with data-backed technical arguments
Build, test, and maintain automated workflows powering the AI Chat Platform
Requirements
1–3+ years of relevant technical experience in Technical Operations, Systems Analysis, Data QA, Software QA, or Workflow Automation
Direct responsibility for building, troubleshooting, and maintaining data-driven processes
Ability to write performant SQL beyond basic queries, including CTEs, window functions, and query optimization
Foundational familiarity with Python or scripting for data manipulation
Practical experience with workflow engines, API integrations, or orchestration platforms such as n8n, Workato, Make, Retool, or equivalent native workflow tools
Engineering-minded QA instincts, including edge-case handling, monitoring, rollback plans, and system dependencies
Applied AI fluency using LLM tools to parse unstructured error strings, structure disparate datasets, and validate logic
Ability to communicate technically with software engineers and explain operational impacts to business partners
Legally eligible to work in Canada
Permanent residence in Canada
Benefits
Top-tier health benefits and life insurance
Long-term group savings with employer match, through Wealthsimple for Business
20 vacation days per year
4 wellness days per year
Unlimited sick and mental health days per year*
Work outside Canada for up to 90 days per year*
Employee resource groups, including Rainbow (2SLGBTQ), Women of WS, and Black at WS
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