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AI Support Engineer - Toronto

OpenAI· User Operations
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RemoteCA$200k - CA$290k + equityFull-timePosted 2mo ago

About the role

Toronto-based, remote-friendly role within OpenAI’s User Operations team, focusing on solving complex technical issues for customers, driving operational excellence, and shaping world-class post-AGI support.

Responsibilities

  • Work directly with customers to troubleshoot and resolve their most complex technical issues, including API failures, integration challenges, authentication errors, and production incidents.
  • Become a trusted expert on OpenAI’s products and platform, serving as a go-to resource for complex technical issues.
  • Serve as a critical escalation point and line of defense for complex technical issues, partnering 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.
  • Take learnings from resolving customer issues and creating our approach to scaling these solutions, partnering with Product and Go-To-Market teams.
  • Drive 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.
  • Provide occasional holiday and weekend support on call coverage, as needed, to support business and customer needs.

Qualifications

  • Have 5+ 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 (e.g., Codex, ChatGPT, OpenAI API) 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 calm demeanor 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.
  • Excellent critical thinking and problem-solving abilities 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.
  • Bachelor’s degree in Computer Science, Computer Engineering, another relevant technical field, or equivalent practical experience.

Skills

Required:API troubleshootingSaaS troubleshootingScripting / automationCustomer communication

Benefits

  • Medical, dental, and vision insurance for you and your family
  • Paid parental leave (up to 24 weeks for birth parents and 20 weeks for non-birthing parents)
  • Paid time off: accrual of 20 days per calendar year
  • 12+ paid company holidays, and multiple paid coordinated company office closures throughout the year for focus and recharge, plus paid sick time
Last updated Sep 3, 2026. Interested? Apply on the company site.

About OpenAI

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Company profileWebsite

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