AI Support Engineer - Toronto (Weekend Shift)

About the Team OpenAI’s User Operations team shepherds our customers’ adoption of AI and ensures that our customers' product experience is nothing short of exceptional. We are building the very first post-AGI support team. We resolve complex issues, provide technical guidance, and support customers in maximizing value and adoption from deploying our products. We work closely with Sales, Technical Success, Product, Engineering and others, to deliver the best possible experience to our customers at scale. OpenAI's customers represent a range of diverse backgrounds and maturity, from early-stage startups to established global enterprises. About the Role 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, v