AI Support Engineer - Toronto (Weekend Shift)

We’re looking for dedicated, experienced, and deeply curious individuals to help solve some of the most complex challenges faced by our customers while building the future of post-AGI support alongside us. In this role, you’ll work directly with customers through support tickets and live calls, troubleshooting high-impact issues and resolving novel, often ambiguous technical problems in one of the fastest-moving environments in technology. As AI adoption rapidly accelerates, the work you do will directly support mission-critical systems being built on OpenAI’s platform, serving as a critical line of defense for customers operating at massive scale.

Beyond resolving technical issues, you’ll help define what world-class support looks like in an AGI-driven future. You’ll partner closely with Engineering, Product, and Operations to improve systems, reduce bugs, and elevate the customer experience, while leveraging automation, agents, and our own AI technology to transform how support operates at scale.

Note: each person in this role will be expected to work a standard 5x8 work week, with 1 of the days covering weekend shifts each week (e.g., work weeks covering Tuesday - Saturday or Sunday - Thursday)

You’ll be responsible for:

• 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.

You might thrive in this role if you have:

• 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.

About OpenAI

OpenAI is an AI research and deployment company dedicated to ensuring that general-purpose artificial intelligence benefits all of humanity. We push the boundaries of the capabilities of AI systems and seek to safely deploy them to the world through our products. AI is an extremely powerful tool that must be created with safety and human needs at its core, and to achieve our mission, we must encompass and value the many different perspectives, voices, and experiences that form the full spectrum of humanity.

We are an equal opportunity employer, and we do not discriminate on the basis of race, religion, color, national origin, sex, sexual orientation, age, veteran status, disability, genetic information, or other applicable legally protected characteristic.

For additional information, please see OpenAI’s Affirmative Action and Equal Employment Opportunity Policy Statement.

Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the San Francisco Fair Chance Ordinance, the Los Angeles County Fair Chance Ordinance for Employers, and the California Fair Chance Act, for US-based candidates. For unincorporated Los Angeles County workers: we reasonably believe that criminal history may have a direct, adverse and negative relationship with the following job duties, potentially resulting in the withdrawal of a conditional offer of employment: protect computer hardware entrusted to you from theft, loss or damage; return all computer hardware in your possession (including the data contained therein) upon termination of employment or end of assignment; and maintain the confidentiality of proprietary, confidential, and non-public information. In addition, job duties require access to secure and protected information technology systems and related data security obligations.

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At OpenAI, we believe artificial intelligence has the potential to help people solve immense global challenges, and we want the upside of AI to be widely shared. Join us in shaping the future of technology.