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AI Support Engineer - Toronto (Weekend Shift)

OpenAI - Remote - Remote - posted 2026-09-28

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OpenAI's User Operations team is seeking an experienced AI Support Engineer to help resolve complex technical challenges for customers deploying AI at scale. You'll work directly with enterprise and startup customers through support tickets and live calls, troubleshooting high-impact issues including API failures, integration challenges, authentication errors, and production incidents. You'll provide end-to-end ownership through debugging, log analysis, issue reproduction, and expert technical guidance. Beyond reactive support, you'll help define what world-class support looks like in an AGI-driven future. You'll partner closely with Engineering, Product, and Operations teams to improve systems, reduce bugs, and elevate customer experience. You'll leverage automation, AI agents, and OpenAI's own technology to transform how support operates at scale. You'll identify opportunities for automation and AI-powered workflows, implement scalable improvements, and drive operational excellence by reducing manual effort. The role involves working a standard 5x8 work week with one day per week covering weekend shifts (e.g., Tuesday–Saturday or Sunday–Thursday). You'll serve as a critical escalation point for complex technical issues, becoming a trusted expert on OpenAI's products and platform. You'll take learnings from customer issues and partner with Product and Go-To-Market teams to scale solutions. Occasional holiday and weekend on-call support is required as needed. QUALIFICATIONS: - 8+ years of experience in User Operations, Engineering, Support Engineering, or similar technical roles, ideally in high-growth tech startups or fast-paced environments - Expert-level SaaS troubleshooting skills with ability to rapidly understand new technologies and complex concepts - Comfortable using emerging technologies (Codex, ChatGPT, OpenAI API) to script or engineer code (e.g., Python) for automating repetitive tasks and integrating tools - Polished enterprise communication skills; calm and effective during high-stakes customer incident calls - Proven experience building strong relationships with customers and cross-functional partners to drive resolution of complex issues - Exceptional critical thinking and problem-solving ability; clear communication of complex technical issues to both customers and internal teams - Ability to thrive in ambiguity, adapt rapidly to change, continuously learn, and proactively seek growth opportunities - Humble, team-first mindset with genuine eagerness to help others and curiosity to quickly learn needed knowledge - Bachelor's degree in Computer Science, Computer Engineering, or another relevant technical field, or equivalent practical experience

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