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AI Support Engineer - Toronto (Weekend Shift)

OpenAI· User Operations
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Ontario - RemoteFull-timePosted 3w ago

About the role

OpenAI is seeking an AI Support Engineer on the weekend shift to troubleshoot high-impact technical issues, work directly with customers, and help define world-class post-AGI support. The role combines hands-on incident resolution, collaboration with Engineering and Product, and development of scalable, AI-powered support workflows.

Responsibilities

  • Working directly with customers to troubleshoot and resolve their most complex technical issues, including API failures, integration challenges, authentication errors, and production incidents. Providing end-to-end ownership through debugging logs, analyzing system behavior, reproducing issues, and delivering expert guidance.
  • Becoming a trusted expert on OpenAI’s products and platform, serving as a go-to resource for complex technical issues.
  • Serving as a critical escalation point and line of defense for complex technical issues, partnering closely with customers and Engineering teams to troubleshoot, resolve, and proactively prevent recurring problems while leveraging scripting and emerging AI capabilities to improve internal tooling and automate operational workflows
  • Taking learnings from resolving customer issues and creating our approach to scaling these solutions, partnering with Product and Go-To-Market teams.
  • Driving operational excellence by identifying opportunities for automation and AI-powered workflows, implementing scalable improvements that increase team efficiency, reducing manual effort, and elevating the overall support experience.
  • Providing occasional holiday and weekend support on call coverage, as needed, to support business and customer needs.

Qualifications

  • Have 8+ years of experience in User Operations, Engineering, Support Engineering or similar technical roles, ideally within high-growth tech startups or other fast-paced environments.
  • Are comfortable using emerging technologies (ie. Codex, ChatGPT, OpenAI API, etc.) to script or engineer code (e.g., Python) for automating repetitive tasks and integrating tools.
  • Have expert-level SaaS troubleshooting skills with the ability to rapidly understand new technologies and complex concepts.
  • Polished enterprise communication and are calm with high-stakes customers during live incident calls.
  • Proven experience building strong relationships with customers and cross-functional partners to drive resolution to complex issues.
  • Exceptional critical thinker and problem solver with the ability to clearly communicate complex technical issues to both customers and internal teams.
  • Thrive in ambiguity, adapt rapidly to change, continuously learn, and proactively seek opportunities for growth.
  • Bring a humble, team first mindset, a genuine eagerness to help others, and the curiosity to quickly learn whatever knowledge is needed to help both your teammates and our customers succeed.
  • Bachelor’s degree in Computer Science, Computer Engineering, another relevant technical field, or equivalent practical experience.
Last updated Oct 1, 2026. Interested? Apply on the company site.

About OpenAI

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